Taylor Swift’s 50 Hottest Outfits
By Ani Bundel
Taylor Swift ever evolving fashion choices over the years have yielded more hit than they have misses, which is remarkable considering she grew up in the public eye. Her outfits from the first have always been true to her own style and always in keeping with the image and brand she was trying to project, which is a remarkable amount of self possession for one so young. Today we’re counting down the 50 Hottest Outfits she’s worn over the years, with an eye to Swift’s ever evolving style from then to now.
Next: Number 50: The 2006 ACMs
Taylor Swift during 41st Annual Academy of Country Music Awards – Arrivals at MGM Grand Theater in Las Vegas, Nevada, United States. (Photo by Jeff Kravitz/FilmMagic, Inc)
50. 2006 ACMs, in BCBG Maz Azria
Our first look is one of Taylor’s first red carpet appearances, at the 2006 American County Music Awards. held only months after her first album had dropped, this was one of her first forays into wearing actual designer dresses. You wouldn’t know it though. Though she looks age appropriate here, it’s also shockingly casual for a red carpet, and for the red carpet of an event that considers itself a cut above that other County Music Award group. Still, it’s Taylor keeping to a certain look, and one that she was sporting regularly at the time–the young high school ethereal hippie in cowboy boots. Commitment to the way she was trying to present herself is very admirable and understandable, but perhaps not appropriate for the venue.
Singer Taylor Swift arrives at the 44th Annual CMA Awards at the Bridgestone Arena on November 10, 2010 in Nashville, Tennessee.
49. 2010 CMAs, in Monique Lhuillier
Taylor’s look in her earlier years took some time to evolve. Looking back over the dresses she wore can sometimes feel like watching a teenager try different looks on to figure out who she is–which, to be fair, was exactly what she was doing. It’s just that most teenagers aren’t doing it on a global stage. This Monique Lhuillier gown at the 2010 CMAs feels like an attempt at Jessica Rabbit–not bad, just drawn that way. Cute, certainly. The hair and make up are both flawless. Above the neck, I have no complaints. But the gown just feels like it’s trying too hard. Swift’s whole persona is exactly the opposite of Jessica Rabbit–she’s not bad at all, but sweet and innocent. Drawings don’t become her.
Taylor Swift (Photo by Rick Diamond/WireImage)
48. 2006 CMAs in Sandy Spika
Get used to the name Sandy Spika, you’ll be seeing Taylor wearing a lot of her in the early years. No, she’s not some off the beaten track high end fashion designer you’ve never heard of, that only Taylor knew about. Spika is the wife of Swift’s producer Scott Borchetta. Remember, Borchetta was a nobody with a company he was just starting out when he discovered Swift. She made his career just as much as he made hers. And in those early years, he was working to sell her as hard as she was, and that included having his wife design and sew her red carpet looks. This one might have been panned as a bit to Elvira at the time, but I think the real problem is the huge country hair and the make up that’s doing a Renee Zellwegger number on her eyes.
Next: Number 47: 2007 Opening Act
Taylor Swift (Photo by Jason Squires/WireImage)
47. 2007 Tour Performance Outfit
Much like her appearance at the American County Music Awards that spring, Taylor’s professional outfits were all aiming for that Midwestern high schooler hippie vibe, head in the clouds clothing, with the down to earth country boots keeping her rooted. She had a theme, and she stuck with it. This is one of my favorites of her earliest performance outfits, from when she was performing in Kansas City in 2007. The white and gold floral paisley print reads wholesome and innocent high school girl from afar, while setting off the woodgrain of her guitar nicely. (The girl-with-guitar persona means the guitar has to match.) Meanwhile the brown cowboy boots are both a nicely matching pop of color as well as adding a comfortable cowgirl vibe to the proceedings. Note they too have paisley like shapes worked into them for a full head to toe theme.
LOS ANGELES, CA – NOVEMBER 21: Taylor Swift attends the 38th Annual American Music Awards at Nokia Live on November 21, 2010 in Los Angeles, California. (Photo by Gregg DeGuire/FilmMagic)
46. 2010 AMAs in Collette Dinnigan
Taylor’s other “bad” habit on the carpet–when she wasn’t wearing gowns that try too hard, or designs from her producer’s wife, was a love of the flashy and sparkly gown. There was a point in her career when you could guarantee that if Swift was showing up to a red carpet, it would be beaded, metallic and sparkly. This was one of her better efforts in that department, a Collette Dinnigan cocktail number for the 2010 AMAs right at she was parlaying her Fearless crossover success into her new album, Speak Now. The beads are a bit on the oversized side, but in general the short hem and the straightened hair are a good first attempt at stepping from the country music world into one of pop chart success.
Next: Number 45: 2013 Met Gala
NEW YORK, NY – MAY 06: Taylor Swift attends the Costume Institute Gala for the “PUNK: Chaos to Couture” exhibition at the Metropolitan Museum of Art on May 6, 2013 in New York City. (Photo by Stephen Lovekin/FilmMagic)
45. 2013 Met Gala in J.Mendel
Taylor loves the Met Gala, and ever since getting her first invite to what is known as the Fashion World’s Oscar event, she’s gone every single year, no matter what the theme. Speaking of themes, the Met Ball always tries to coordinate the theme they want their stars to wear to the red carpet with whatever the collection the Metropolitan Museum Fashion Wing is showing. Unfortunately for Swift, in 2013, the theme was punk. She might have done better to ignore it (as many who came the event that night did.) But Swift is team player. They say punk–she’s going to go to J. Mendel and say “We’re doing punk. Whatcha got?” This was the answer. The gown itself is not bad on her–I would have liked to see it with an updo maybe, and a different make up job. But the over kholed eyes and the teased hair that she wore down didn’t help matters. A for effort anyway.
Singer/songwriter Taylor Swift arrives at the 41st Annual CMA Awards at the Sommet Center on November 7, 2007 in Nashville TN. (Photo by Michael Loccisano/FilmMagic)
44. 2007 CMAs in Sandy Spika
“Taylor Swift Surprised Face” is something of a ongoing joke, as Taylor swept award after award in her career, and every time looked as shocked and grateful as the first time. Speaking of the first time, here it is. In 2007, Taylor took home the CMAs Horizon Award, given out to the most promising new artist. But the gown was a little less so. I get that the way Borchetta wanted to sell her, and Taylor herself wanted to be perceived was “Country Disney Princess,” but Spika took it a little too literal and actually made a knock off version of Belle’s gown from Beauty and the Beast. Let’s not ask who the beast is here. I’m sure she’s written a song about him though.
Next: Number 43: 2010 BMI Awards
NASHVILLE, TN – NOVEMBER 16: Taylor Swift attends the 58th Annual BMI Country Music Awards at BMI on November 9, 2010 in Nashville, Tennessee. (Photo by Andrew H. Walker/Getty Images for BMI)
43. 2010 BMI Awards in Zspoke by Zac Posen
Taylor Swift doesn’t wear enough cocktail dresses. This is not a criticism–she has insisted most profusely that she is a gown girl. She likes long dresses, and she likes princessing it up. And fairy tale princesses don’t usually show up to the ball in a cocktail dress. (Though we should point out for the record that not having long poufy skirts to hike up and carry would have made Cinderalla’s flight from the ball at midnight far easier. But I digress!) The point is, Taylor is very tall, and naturally thin. She has legs, as they say, that go on for days. And she keeps hiding them under skirts. As we can see from this Zac Posen number she wore to the BMIs in 2010, she should maybe consider flashing them more often.
Next: Number 42: 2014 SStreet Style
NEW YORK, NY – JULY 24: Taylor Swift is sighted in Central Park on July 24, 2014 in New York City. (Photo by Alo Ceballos/GC Images)
42. 2014 Street Style, Alice+Olivia
Ah yes, Taylor’s 2014 “Sidewalk Tour” as fashionistas Tom and Lorenzo dubbed it. All though out 2014 as she worked to rehabilitate her imagine as some sort of crazed maneater, Taylor did an entire series of “walks” around new York City, always in a designer clothes, usually sporting a designer purse that was oversized for the amount of stuff she was probably carting around and always with the paparazzi and a big smile in tow. We’ll have a couple of the looks from that tour throughout the countdown, but clocking in first is this Alice + Olivia two piece outfit. This is one of my favorites because it’s literally almost the same cut as one of her on stage outfits from that year, just the dressed down comfy looking version. Now that’s sticking to a style.
LOS ANGELES, CA – FEBRUARY 10: Singer Taylor Swift arrives to the 50th Annual GRAMMY Awards at the Staples Center on February 10, 2008 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
41. 2008 Grammys in Sandy Spika
There are things I really like about this 2008 Sandy Spika number. During Swift’s Fearless campaign, she was working the medieval angle pretty hard, and this dress is definitely working to channel that. And though it might put me in the minority, I actually like the blue and purple vine appliques on the skirt. They’re pretty! They’re girly! They also make it feel a little bit like a costume, instead of a red carpet gown. But Taylor clearly loves the hell out of it, so there you go. And in a sea of safety colors –red, beige, black–going deep blues and purples is to be commended, even if parts of the dress don’t really hit the mark.
Next: Number 40: 2012 Teen Choice Awards
UNIVERSAL CITY, CA – JULY 22: Musician Taylor Swift arrives at the 2012 Teen Choice Awards at Gibson Amphitheatre on July 22, 2012 in Universal City, California. (Photo by Jason Merritt/Getty Images)
40. 2012 Teen Choice Awards in Marcia Lucia Hohan
What did I just say about Taylor and short hems? Exactly. Here we have her in a cute cocktail number from Marcia Lucia Hohan. There are arguments that this gown isn’t quite red carpet level–it’s a little on the casual beachy night side of things. But it’s the Teen Choice Awards. Held in the high of summer, this marries all the pretty things that Taylor loves–the chiffon folding, the romantic hemline, the pretty princess style, and dresses it up just enough to match the event perfectly. Even better–it’s age appropriate, in a venue that’s almost always filled with those over 30 dressing like fifteen year olds, while the 15 year olds where styles that double their age for the camera. Thank heavens.
NASHVILLE, TN – NOVEMBER 12: Musician Taylor Swift attends the 42nd Annual CMA Awards at the Sommet Center on November 12, 2008 in Nashville, Tennessee. (Photo by Jemal Countess/WireImage)
39. 2008 CMAs in Kaufman Franco
When Taylor Swift likes a designer, she has a tendency to stick with them for several occasions in a row. This slow yet steady approach to changing looks is why she wore so much Sandy Spika as long as she did. But when she finally moved on, is was to another designer whose name we’ll see regularly on this countdown–that of the design team of Ken Kaufman and Isaac Franco, otherwise known as Kaufman Franco. The duo had only been producing their line for about four years when Swift began to turn to them with regularity. they were her first step into a more mature look, and also coincided with her sparkle and metallic phase, as we can see above for the 2008 CMA awards. The hair’s pretty on point too, but the make up is still making her eyes look square.
LAS VEGAS – MAY 14: Music artist Taylor Swift performs during the Academy of Country Music New Artists’ Party for a Cause show at the MGM Grand Conference Center May 14, 2007 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
38. 2007 ACM Performance Outfit
Moving up in the performance outfit category. We’ve still got Taylor doing the “grounded girl in country boots” look. But the dress is no longer channeling high schooler with her head in the clouds. This is a “young country superstar” look. It’s still young and fresh, with frilly edges and tiers, but there’s an added sparkle with the sequins and the embroidered lines. And much like her last performance outfit the color is very well chosen to offset the wooden finish of the guitar. (Details like that matter!) And notice that the boots now are much closer in color to matching instead of clashing. Also, unlike before, they now are personalized. Taylor Swift is somebody.
Next: Number 37: 2011 Met Gala
Taylor Swift attends the ‘Alexander McQueen: Savage Beauty’ Costume Institute Gala at The Metropolitan Museum of Art on May 2, 2011. AFP PHOTO / TIMOTHY A. CLARY (Photo credit should read TIMOTHY A. CLARY/AFP/Getty Images)
37. 2011 Met Gala in J.Mendel
The 2011 Met Ball was Swift’s second outing to the Fashion Oscars. The theme was another one where she played along gamely, though it probably didn’t suit her sense of style as well as she might have if she had just ignored it. The carpet was dedicated to the late Alexander McQueen, who had taken his own life only a year or so earlier. Swift had the presence of mind not to wear a McQueen gown–that never would have suited her. Instead she went for another edgy designer who still has the soft girly girl undertones that she was looking for: J.Mendel. Mendel would later on become one of her go-to choices for red carpet wear, and the details of this dress show why. Though the bottom might be fairly perplexing, the lace applique pieces are both feminine and interestingly laid. it’s certainly an outfit that’s worth looking at twice, and that’s always a bonus when it comes to a red carpet appearance.
Next: Number 356: 2012 Grammys
LOS ANGELES, CA – FEBRUARY 12: Singer Taylor Swift arrives at the 54th Annual GRAMMY Awards held at Staples Center on February 12, 2012 in Los Angeles, California. (Photo by Jason Merritt/Getty Images)
36. 2012 Grammys in Zuhair Murad
I love this dress. If Taylor is looking for the gold ball gown of Belle and the metallic sparkle to flash under the lights of the cameras, this is a perfect marriage of the two. It’s got just enough of a train to cause drama and OMG the back is just to die for.
But the designer of this dress is not one that flatter’s Taylor’s natural looks. The neck is too high, the pattern of the design is too blocky and the slicked back hair is too severe. Much like her Jessica Rabbit look earlier, this feels like Taylor is attempting to play at pop diva instead of simply being one. It is a gown more for Jennifer Lopez than Swift. (No surprise that Murad is actually Lopez’s go to designer.) Which is too bad, because I can see why she loved it so much.
Next: Number 35: 2013 Red Tour
FOXBORO, MA – JULY 27: Taylor Swift performs onstage at Gillette Stadium in Foxborough, Mass. in front of a sold-out crowd of more than 55,000 fans. (Photo by Theo Wargo/TAS/Getty Images for TAS)
35. 2013 Red Tour Performance Outfit
With this outfit, we start getting to what I would call Taylor’s “iconic” outfits. The striped top with the three quarter sleeves became something of a calling card for Swift during her promotional tour of the Red album. Google “Taylor Swift, stripes” and you’ll get a whole host of pictures of Swift in variations of this blouse all dating from mid 2012 through the end of 2013. (One think I can’t get over about Taylor is her fanatical attention to these sort of details. Girl picks a head turning look and then makes sure to do variations in all situations in order to guarantee everyone will see her wearing it at least once.) For this countdown, I chose the version she wore for the Red Tour with another staple of her wardrobe–the high waisted hot pants. In red, natch! Casual, yet memorable.
ARLINGTON, TX – APRIL 19: Taylor Swift makes her way to the stage during the 50th Academy of Country Music Awards at AT&T Stadium on April 19, 2015 in Arlington, Texas. (Photo by Kevin Winter/ACM2015/Getty Images for dcp)
34. 2015 ACMs in Reem Acra
The ACMs are one of the high points of the country music awards calendar, and if they are celebrating their 50th anniversary, everyone is going to show up.. And though by 2015, Taylor had basically left the country world behind to go conquer larger shores, the country music scene wasn’t nearly ready to let her go. Note this isn’t a red carpet shot though. Swift skipped that part and only showed up for the ceremony itself, where she received one of the Milestone Awards that were given out that night to the most notable country acts in the last fifty years. Still,t eh dress, a mint colored Reem Acra spoke volumes about how far Swift had come in her style and the industry in only a few short years.
Next: Number 33: 2013 Brit Awards
LONDON, ENGLAND – FEBRUARY 20: Taylor Swift attends The Brit Awards 2013 at The O2 Arena on February 20, 2013 in London, England. (Photo by Dave J Hogan/Getty Images)
33. 2013 Brit Awards in Elie Saab
The year 2013 was one where Taylor made great strides in leaving behind her country roots and becoming more pop focused with the release of her album Red, and several cross over successive hits. Her style evolution matched that, especially when she crossed the pond to attend the Brit Awards that year. The UK is the home to great many cultural things, but US Country Music is not the mainstream sound or style, and so Swift took this opportunity to test drive the more minimalist and sexy lines that she would begin to sport as she left the country scene behind–note that even her hair is thoroughly straightened too. the only curves to be found in the entire outfit are the snake like gold lines on her shoes.
Next: Number 32: 2014 Street Style, Part 2
NEW YORK, NY – JULY 30: Singer Taylor Swift is seen on July 30, 2014 in New York City. (Photo by XPX/Star Max/GC Images)
32. 2014 Street Style, Novis
Another gorgeous look of Taylor’s, from the period of her 2014 Summertime Street Tour of New York City. I love this Novis number for all the opposite reasons I liked the other one. This one, with the sparkly silver overlay and the bright silver heels is so hilariously impractical for the height of NYC’s stuffy and smelly hot summers. Here she is in something that looks like it’s more appropriate for an casual evening industry party. She looks cool and soft in the hard city around her, without a drop of sweat or even slightly ruffled by the scene around her. it is the very definition of having a designer outfit you want to show off and nowhere to do so, and therefore making the sidewalk your catwalk. Fantastic.
Singer Taylor Swift arrives at the 51st Annual Grammy Awards at the Staples Center on February 8, 2009 in Los Angeles, California. (Photo by Jon Kopaloff/FilmMagic)
31. 2009 Grammys in Kaufman Franco
Another Swift foray into mature looks in another Kaufman Franco gown, this time for the very high end, and very televised 2009 Grammy Awards. This would be the year just before her Speak now album would speak every category it was nominated in. She certainly is working towards stepping up from the “pretty princess” look to something more mature, with this black number with a neckline that plunged nearly to the belly button. I think the hem is a touch too long personally, though note that in sensible fashion the skirt is split so she has no problem walking in it. The idea is clearly a train, but the way it pools around her feet when she stands still doesn’t do that part justice. But in terms of stepping up the sex appeal, this was a huge leap forward.
LOS ANGELES, CA – NOVEMBER 20: Taylor Swift arrives at the 2011 American Music Awards at Nokia Theatre L.A. Live on November 20, 2011 in Los Angeles, California. (Photo by C Flanigan/FilmMagic)
30. 2011 AMAs in Reem Acra
Sparkly metallic gowns and princess gowns. Those were Taylor’s early go-tos in her red carpet career. On a few occasions she combined them, but not always to the best effect. This one was one of the better ones. Ree Acra is exactly the sort of designer where sparkly and princess are right in his wheelhouse, so it’s no surprise that his was one of the winning combinations. Of course, Acra is also one who does a lot of bridesmaids gowns, so much of his work can easily fall that way. And though the halter top nature of this gown is a little basic, the cut and the sheer overwhelming burst of light from the gown more than make up for it. Not so much in love with the hair those. Not sure if it’s the styling to the side, but it looks more tired than straightened.
Next: Number 29: 2010 People's Choice
LOS ANGELES, CA – JANUARY 06: Singer Taylor Swift poses with the Favorite Female Artist Award in the press room during the People’s Choice Awards 2010 held at Nokia Theatre L.A. Live on January 6, 2010 in Los Angeles, California. (Photo by Jason Merritt/Getty Images for PCA)
29. 2010 People’s Choice Awards in Jenny Packham
Who says one can’t be a pretty pretty princess in high hemlines? Some might call this Jenny Packham number (a designer, by the way, who does much of real-life princess Kate Middleton’s looks) a touch on the wedding side, but I think it’s spectacular. It captures everything about Taylor that she’s trying to express through her clothing. It’s girly. it’s frilly, it’s sparkly. It;’s got a fantastical amount of detail considering that it’s barely 3′ of fabric square. It shows off Taylor’s legs to fantastical effect, as well as her arms. My only quibble with the entire look is that this is still the era where whoever did her make up wasn’t doing her eyes nearly enough justice.
Next: Number 28: 2011 Speak Now
NEW YORK, NY – NOVEMBER 22: Taylor Swift performs onstage during the “Speak Now World Tour” at Madison Square Garden on November 22, 2011 in New York City. Taylor Swift wrapped up the North American leg of her SPEAK NOW WORLD TOUR with two sold-out shows at Madison Square Garden this week. In 2011, the tour played to capacity crowds in stadiums and arenas over 98 shows in 17 countries spanning three continents, and will continue in 2012 with shows Australia and New Zealand. (Photo by Larry Busacca/Getty Images)
28. 2011 Speak Now Tour Performance Outfit
The metallic sparkly outfit to end all metallic sparkly outfits during the peak era of Taylor and her metallic sparkly outfits craze. This Speak Now glitter and fringe outfit, which was her closing number on the tour, is actually a designer piece, made by Roberto Cavalli. It was also her first tour outfit that clearly was designed to be worn without a guitar. Not that it doesn’t look great with one–it totally does. But one can see the first major shifts from the “country singer-songerwriter” vibe from her earlier performance outfits to something more big glittery stage show, meant for the pop star style performance.
LAS VEGAS, NV – APRIL 06: Singer Taylor Swift arrives at the 49th Annual Academy of Country Music Awards at the MGM Grand Hotel and Casino on April 6, 2014 in Las Vegas, Nevada. (Photo by Axelle/Bauer-Griffin/FilmMagic)
27. 2014 ACMs in J.Mendel
After eight years of arriving at the American County Music awards every inch a country princess, 2014’s release of 1989 was the year that Taylor said farewell to the niche area of the music industry that catapulted her to fame. Swift was always going to be too big to stay in the country lane. her dreams of world domination simply were too large for Nashville to hold. New pop-driven edgy Taylor arrive at the ACMs in an outfit by her go-to edgy designer, J.Mendel in a two piece number with a slit all the way up one side, her midriff bar, peepholes in the shoulders and a new hairstyle that was leaving the country music scene behind. The album mioght have been a few more months in the releasing, but Taylor was already clearly leaving.
LOS ANGELES, CA – FEBRUARY 08: Singer Taylor Swift arrives at the 57th GRAMMY Awards at Staples Center on February 8, 2015 in Los Angeles, California. (Photo by Jon Kopaloff/FilmMagic)
26. 2015 Grammys in Elie Saab
How does one dress like a pop princess? This seems to be Taylor’s fashion question this year. This high-low gown by Elie Saab for the 2015 Grammys was certainly a stab in the right direction. One might call it a mermaid gown, just due to the color gradation. It shows off more skin that the country style more modest Taylor would have a couple of years ago, with a really short mini hem on the inside, but still has that long dramatic drape with the overskirt. The bodice has interesting cut outs that photograph nicely from the waist up for face-centric shots. My only quibble is the bright fuchsia shoes. Not that I think matchy-matching shoes would have been the right call (too bridesmaid), but this is one instance where a beige “nude” heel would have done the trick without distracting.
Next: Number 25: 2014 Tonight Show
NEW YORK, NY – AUGUST 13: Taylor Swift visits “The Tonight Show Starring Jimmy Fallon” at Rockefeller Center on August 13, 2014 in New York City. (Photo by Theo Wargo/NBC/Getty Images for “The Tonight Show Starring Jimmy Fallon”)
25. 2014 The Tonight Show in Bec and Bridge
Many of Taylor’s casual looks for 2014 come from her long Summer Street Tour of New York City. But I have to say that one look that really stuck out for me was actually worn as part of her promotional TV appearances to promote her 1989 album. This rose patterned minidress, by Australian design team Bec and Bridge, was one she wore for her last night appearance on The Tonight Show with Jimmy Fallon. It’s a really smart choice for TV, with the black and white graphic design that stands out against the blue and brown set. The hem is nice and short so it shows off her legs, but not so short as to seem showy. The recent haircut is also on full display here, curled under into a long bob. And the makeup is subtle–the red lips of the Red years are gone. Swift looks like the harmless girl next door who is merely planning a minor conquest of pop world domination. Nothing to fear, home viewers!
NEW YORK, NY- SEPTEMBER 13: Taylor Swift arrives for the MTV Video Music Awards at Radio City Music Hall on September 13, 2009 in New York City. (Photo by Gregg DeGuire/FilmMagic)
24. 2009 VMAs in Kaufman Franco
It’s the dress everyone has seen Taylor in. It doesn’t matter if you listen to country, pop, rap, R&B, or really, if you don’t listen to radio at all. If you turned on the news at any point in the latter half of 2009, you saw Taylor, wearing this dress, hand over her mouth looking completely dazed as “jackass” Kanye West (the president’s words! Not mine!) walked up and attempted to negate her win for Video of the Year. It’s kind of a shame really, because that last part is the part people remember, and not the beautifully draped silver caftan-esque gown by Kaufman Franco, which was one of the best numbers they put her in during her year and a half of wearing them. We can blame Kanye for that too, right? Right.
LAS VEGAS, NV – MAY 17: Singer Taylor Swift arrives at the 2015 Billboard Music Awards at MGM Garden Arena on May 17, 2015 in Las Vegas, Nevada. (Photo by Axelle/Bauer-Griffin/FilmMagic)
23. 2015 BBMAs in Yves Saint Laurent
Taylor Swift is a self proclaimed “dress girl.” But since releasing 1989 and crossing over into pop stardom, she’s been working hard to break with the past. this was never more obvious than at the Billboard Music Awards earlier this years. In sea of pop star wannabes and looks like were trying way too hard, Swift stuck out as the best dressed on the carpet–and she did it in pants. YSL is not a designer Swift had worn much before, if ever, and the look is so radically different from her other choices that came before it–from the barely there bodice to the wide cut outs on the side–it’s a heck of a head turner. Jumpsuits, and sparkly 70s ones at that, are very now, to be sure, but when Swift is the one riding that fashion trend, it’s worth looking at twice.
Taylor Swift arrives at the 52nd Annual GRAMMY Awards held at Staples Center on January 31, 2010 in Los Angeles, California.
22. 2010 Grammys in Kaufman Franco
Kaufman Franco timed their Swift era perfectly. There are two gowns nearly everyone has seen her in. the first was up above at the 2009 VMA awards, and that was theirs. The other is this Kaufman Franco number, the one she wore to the 2010 Grammys when she proceeded to sweep every category she was nominated in. It’s not a gown many would have worn to the Grammys–not because of the design, but the color, which is a dark navy, is not what you would consider a “safety” color. And the square cut out at the center of the bodice, though daring by Swiftian standards, would probably not come close for the rest of the pop star crowd eager for attention. the same goes for the demur and tasteful accessories. But Taylor didn’t need to dress for attention. the five Grammy Awards she walked around juggling in this dress after the ceremony was plenty accessory enough.
Next: Number 21: 2015 1989 Tour
TOKYO, JAPAN – MAY 05: Taylor Swift performs during The 1989 World Tour at Tokyo Dome on May 5, 2015 in Tokyo, Japan. (Photo by Jun Sato/LP5/Getty Images for TS)
21. 2015 1989 Tour Performance Outfit
How far Taylor has come in her performance outfits since those early hippie dresses. The cowboy boots are long gone, replaced by hip trendy heel booties. And the outfits? Well, they are desined to show off just how good Taylor looks and just how in shape she is at 25 years of age. The long curls that swing around as she performs have also gone the way of the cowboy boots, with a slick, straightened bob that stays out of her face at all times. This is an outfit that shows no plans to be weilding a guitar while she’s wearing it. The only nod to her old style choices is the shiny patterned designer skirt, and even that is so short as to be a little eyebrow raising. But ti’s still Swiftian though–note that there’s no bellybutton. She may be pop, but she’s still got standards of decency.
Taylor Swift during 42nd Academy of Country Music Awards – Arrivals at MGM Grand Hotel and Casino Resort in Las Vegas, Nevada, United States. (Photo by Jon Kopaloff/FilmMagic)
20. 2007 ACMs in Sandy Spika
Our last of the Sandy Spika gowns on the list. This one, for the 2007 American Country Music awards, notches in notably higher than the other ones, and that’s because it’s the one time the designer really knocked it out of the park for her young charge. Taylor Siwft in 2007 was looking for the pretty country princess look, and this one delivers in spades. Everything about it is on point, from the pale pink beaded bodice that suggests medieval without going overboard into costume, a long trailing skirt that is nonetheless not overdone. And for once the hair and the makeup are both on point. The curly hair is swept into a romantic updo, and the eyes are done to show them off instead of receding them into her face. Bravo.
Next: Number 19: 2013 Golden Globes
BEVERLY HILLS, CA – JANUARY 13: Taylor Swift arrives at the 70th Annual Golden Globe Awards at The Beverly Hilton Hotel on January 13, 2013 in Beverly Hills, California. (Photo by Steve Granitz/WireImage)
19. 2013 Golden Globes in Donna Karen
Taylor’s first trip to the Golden Globes came courtesy of her nomination for The Hunger Games soundtrack. It was her first major televised A-list awards show invite outside of the Grammys, which meant stepping up her red carpet game. To do so she chose this wine colored Donna Karen number, with a plunging back and sheer side panels. It was an Old Hollywood goes pop star glam type design that suited her well. The Grace Kelly hair and the natural make up look that she paired with it spoke to the serious songwriter musician she wants to be thought of, which still reveling in the fact that she’s in her early 20s and can get away with being thoroughly sexy. She may not have taken home the hardware, but she certainly dressed the part anyway.
Next: Number 18: 2015 Street Style
LOS ANGELES, CA – JANUARY 14: Taylor Swift is seen on January 14, 2015 in Los Angeles, California. (Photo by Bauer-Griffin/GC Images)
18. 2015 Street Style, Free People
Taylor continued her Street as Catwalk tour that served her so well in 2014 into 2015. This is one of my favorites, because it speaks to everything Taylor is trying to present about herself currently–stylish, trendy, bit of a hippie, a natural girl next door. (Next door just happening to be a multi-million dollar condo in the tony part of NYC.) But even better, she’s doing it in an outfit that most girls her age not only would wear, but could afford. Free People is a spin off line from the ubiquitous Urban Outfitters brand. (It was actually called “Free People” before it was named Urban Outfitters.) geared towards the young to mid 20 something crowd, it is exactly the sort of thing Swift’s contemporaries are wearing too. A reminder that though she might be an international superstar, Taylor swift is just like us.
Next: Number 17: 2014 Golden Globes
BEVERLY HILLS, CA – JANUARY 12: Singer Taylor Swift attends the 71st Annual Golden Globe Awards held at The Beverly Hilton Hotel on January 12, 2014 in Beverly Hills, California. (Photo by Jason Merritt/Getty Images)
17. 2014 Golden Globes in Carolina Herrera
Taylor’s second trip to the golden Globes wasn’t as pleasant as her first. Most people remember the fact that Tina Fey and Amy Poehler decided to make her the butt of man eater jokes, which unfortunately solidified a negative image about the singer that had been nebulously forming ever since she used her powers for good and killed professional douchebro John Mayer’s career. The resulting retrenchment on Swift’s part helped unleash the 2014 Sidewalk Tour as well as Swift’s Girl Gang of buddies. But what most people don’t remember is the two toned Carolina Herrera gown that Swift wore to the event, which–like the Donna Karen–was another knock out performance in an Old Hollywood style, serious artist vibe red carpet moments. Matched with the side curls and the on point makeup, it was definitely the better of her two turns on the A List carpet.
LAS VEGAS, NV – APRIL 01: Singer Taylor Swift arrives at the 47th Annual Academy Of Country Music Awards held at the MGM Grand Garden Arena on April 1, 2012 in Las Vegas, Nevada. (Photo by Jon Kopaloff/FilmMagic)
16. 2012 ACMs in J.Mendel
J. Mendel has been a good designer to Swift throughout her time relying on his edgy designs. The trick to Taylor when she looks “edgy” is that she still project that innocent and wholesome vibe. This gown threaded that needle perfectly with modern clean lines in white, with only the minimal amount of gold lame inserts–one at the bodice and one that hit at mid thigh and expanded down to the ground, creating the smallest of trains. There are sexy cut out panels on the sides, but they are demur enough and show so little as to almost be overlooked by the casual observer. The straightened hair matches the dress lines, and though the bangs might feel a touch heavy, the overall effect is perfect.
Next: Number 15: 2015 IHeartRadio
LOS ANGELES, CA – MARCH 29: Singers Madonna (L) and Taylor Swift perform onstage during the 2015 iHeartRadio Music Awards which broadcasted live on NBC from The Shrine Auditorium on March 29, 2015 in Los Angeles, California. (Photo by Kevin Winter/Getty Images for iHeartMedia)
15. 2015 IHeartRadio Performance Outfit
Now, before you get a little shocked by Taylor’s semi boudoir borderline BDSM outfit from the IHeartRadio performance with Madonna, realize this isn’t the first time she’s worn something like it. The Red Tour featured an outfit that was akin to the this with a faux corset top and a bedroom style wrap. It was slightly more demur than this one, but not much. Also remember that this is Taylor’s moment to be anointed by Madonna, as earlier pop stars like Britney and Xtina were once upon a time. After nearly a decade in country, this appearance rocking out on guitar to Madonna’s latest single “Ghost Town” was an acknowledgement by those who had come before that Taylor was part of their world now. It was only fair for her to dress the part, and have a guitar to match.
NEW YORK, NY – AUGUST 25: Taylor Swift attends the 2013 MTV Video Music Awards at the Barclays Center on August 25, 2013 in the Brooklyn borough of New York City. (Photo by James Devaney/WireImage)
14. 2013 VMAs in Hervé Léger by Max Azria
Most people remember Taylor’s 2009 VMAs outfit the best, but I think they should remember this one far more. For the 2013 VMAs, as Taylor experimented with a poppier edgier and sexier look, she did a turn in the style known throughout the industry as the “bandage dress.” Popularized by Max and Lubov Azria, the bandage dress is the staple of their Hervé Léger line. For any hardbodied pop star under a certain age, having one or two on hand to show off in is paramount. For Taylor, who has up until then mostly gone for long flowing pieces that didn’t show off too much skin, the curve hugging and deep neckline plunging outfit was a headturner. Paired with the throwback Old Hollywood style hair and makeup, the result was both modern yet unexpectedly pretty. It’s one Swift should do more often.
Next: Number 13: 2010 Met Gala
Taylor Swift attends the Costume Institute Gala Benefit to celebrate the opening of the ‘American Woman: Fashioning a National Identity’ exhibition at The Metropolitan Museum of Art on May 3, 2010 in New York City. (Photo by Ron Galella/WireImage)
13. 2010 Met Gala in Ralph Lauren
This was Taylor Swift’s first Met Gala. Just getting an invite to the event was proof that in the world of fashion and culture, at least for that minute, she had arrived. But Swift was determined not to allow this to be a one time event. She wanted to be a regular attendee of this premiere fashion red carpet. Also, she was lucky–the theme of this year was “American Woman” which meant her field of choices was wide open in terms of style, and designer. No “punk” directives to follow here. So in dressing to impress she choice the classic gown by Ralph Lauren. The sweet yet minimal simplicity of the gown suited her perfectly. There was a romantic softness to it as well that blended perfectly with the image she was trying to project. Combined with a vintage style hairdo and soft makeup the overall effect was perfect. It was a stunner for a first timer, and a guarantee she would be receiving more invites in the near future.
Next: Number 12: 2014 Cosmo UK
Photo Spread from the UK edition of Cosmopolitan Magazine’s December 2014 Issue (Dress: Valentino. Photograph by James White)
12. 2014 December Issue of Cosmopolitan UK
As Taylor has gotten older, she’s gotten mush better at working it for the cameras in those requisite photoshoots for magazines like Cosmopolitan that come with the promotions of new albums. This one from just under a year ago for Cosmo UK is proof of that. The spread, which credits this as a Valentino gown, put Swift in various snow scapes, allowing her to match Disney’s latest Frozen princesses without being obvious about it. The gown gown against the dark blue and snow background made for a gorgeous two page spread for the beginning of the article, and was one of Swift’s most stunning spreads to date.
NASHVILLE, TN – NOVEMBER 06: Singer Taylor Swift attends the 47th annual CMA Awards at the Bridgestone Arena on November 6, 2013 in Nashville, Tennessee. (Photo by Jon Kopaloff/FilmMagic)
11. 2013 CMAs in Elie Saab
Is it Christmas time already? No, it’s just the 47th CMAs. It was 2013 though and Queen Taylor, as she should at this point be addressed when among her country community, was promoting an album called Red. What color do you think she should wear?
Now, to be fair, this is exactly the sort of design Elie Saab is known for. he does high end ball gowns that are monochromatic, with tone on tone beadwork, tone on tone chiffon and tone on tone lace. So Taylor, though red from head to foot (and lipstick to match) is actually fairly restrained, with only the first of those embellishments on her oversized skirt. What really makes the outfit over the top royalty is the hair make up and earrings. Grace Kelly called and sent her compliments.
LAS VEGAS – APRIL 18: Singer Taylor Swift arrives for the 45th Annual Academy of Country Music Awards at the MGM Grand Garden Arena on April 18, 2010 in Las Vegas, Nevada. (Photo by Denise Truscello/WireImage)
10. 2010 ACMs in Marchesa
If some of Taylor’s greatest looks have come at the Met Gala red carpets, her other red carpet of choice to hit it out of the park seems to be the American Country Music Awards. It’s no accident that this list includes every year she’s attended the event. And though her earliest and her latest appearances at it have not been her greatest hits, it’s her biggest years on the country scene that seem to have brought out the best her her styling. Perhaps that’s because, while there were times in the pop world where you could see her experimenting and trying new styles, here in the country world, she has always known who she is, and been the most confident about her pretty and soft look, such as when she wore this princess goddess style gown by Marchesa (who specializes in just such a gown) in 2010. Paired with the soft hair and the minimal make up, this is one of her best looks to date.
Next: Number 9: 2014 IHeartRadio
LAS VEGAS, NV – SEPTEMBER 19: Recording artist Taylor Swift performs onstage during the 2014 iHeartRadio Music Festival at the MGM Grand Garden Arena on September 19, 2014 in Las Vegas, Nevada. (Photo by Denise Truscello/WireImage)
9. 2014 IHeartRadio Performance Outfit
Back up towards the beginning of this list, I pointed out that Taylor’s street style has a tendency to echo her stage style, in a canny through-line of image management. Here now is that stage outfit I was talking about. Worn as the opening act for the 2014 IHeartRadio music festival, this outfit to me is a perfect balance of the new style that Taylor is working to project as she enters the pop world. She’s never going to be Britney Spears–she too wholesome for that, and that’s why her bellybutton stays firmly covered. But she’s fun and flirty, in bright pink, and covered in rhinestones. She’s the kind of girl you might mistake for a bubbly blonde, masking one of the most canny business women in the business. Get in her way, and one of these days you’ll find those rhinestone boots will walk all over you.
LOS ANGELES, CA – FEBRUARY 10: Singer Taylor Swift attends the 55th Annual GRAMMY Awards at STAPLES Center on February 10, 2013 in Los Angeles, California. (Photo by Jeff Vespa/WireImage)
8. 2013 Grammys in J.Mendel
As I’ve said before, J.Mendel is Taylor’s go-to when she’s trying to go in a more “edgy” direction. But Taylor’s best looks aren’t actually edgy. They play to the dress girl style that she is most comfortable in. Which is why one of her best looks from J.Mendel is this one–the time he took his own more edge style and softened it up into a Grecian goddess type look for Taylor at the 2013 Grammys awards. There’s still a bit of the hard edge to be found, with the silver belt that extends up across the bodice and to the shoulders (conveniently giving just a bit more coverage on the otherwise plunging neckline for the demur Taylor.) The silver also acts as accessories, making it so she needs minimal jewelry. The braided hair across the top of the head actually works the bangs to her advantage, and minimal makeup completes the look.
LAS VEGAS, NV – APRIL 03: Recording Artist Taylor Swift arrives at the 46th Annual Academy Of Country Music Awards at MGM Grand on April 3, 2011 in Las Vegas, Nevada. (Photo by Jon Kopaloff/FilmMagic)
7. 2011 ACMs in Elie Saab
As I said above, Taylor’s biggest years in the country business correspond to her best years at the American Country Music Awards. Her best look at this event came in 2011, after shedding the Sandy Spika years, and moving on to big name designers. This is her every inch a princess, but there’s nothing contrived or costumey about it. After all, this is Elie Saab, who doesn’t make princess outfits as much as he just makes gorgeous gowns geared toward red carpet royalty (which are almost always tone on tone, like the one here.) With this choice of gown, Taylor picks a royal-esque color–gold–without actually making a dress that is cloth of gold. The result is a more refined version of the metallic looks she was favoring during this period in other venues. Since it’s a country event, the hair can sport it’s natural curl, but here the waves are perfectly controlled, and the makeup is certainly there, but not totally in your face. She is every inch the modern country princess.
Next: Number 6: 2015 Street Style Part 2
NEW YORK, NY – JULY 13: Taylor Swift is seen in Tribeca on July 13, 2015 in New York City. (Photo by Alo Ceballos/GC Images)
6. 2015 Street Style, Free People with a Dauphines of New York Headpiece
Speaking of princess, this is probably my favorite of the Street Style moments from this past year. And yes, it’s because she’s wearing a goddamn crown. This, like her last one is another Free People dress, and one you or I could easily afford. But ask yourself. Would you really be able to pull a dress like that off while wearing a crown? The floral Dauphines of New York headpiece she’s sporting on the freshly cut bob is a reminder that just because Taylor is wearing something you or I can afford, she’s not really Just Like Us. She’s the current reigning Queen of Pop.
The only miss for me here is the shoes. Much like her tendency to wear cowboy boots early in her career to symbol her down to earth-ness, these beige Mary Jane heelss are clearly supposed to anchor her majesty to the NYC sidewalks of earth. But I think she should ahve just gone whole hog and worn some sort of impossible shoes that elevated her off the ground.
NASHVILLE, TN – NOVEMBER 09: Recording artist Taylor Swift arrives at the 45th annual CMA Awards at the Bridgestone Arena on November 9, 2011 in Nashville, Tennessee. (Photo by Jon Kopaloff/FilmMagic)
5. 2011 CMAs in J.Mendel
Taylor’s best look from J.Mendel came at the 2011 Country Music Awards red carpet. Taylor might like to think of herself as a mermaid, but she doesn’t always go for the silhouette, preferring to A line Princess gown it instead. But when she does go for this, it always works. The strapless gown wraps her tightly in chiffon and then explodes out of one side on a diagonal forming the train. It might seem a touch bridal, but we’re not asking where the bouquet and aisle are. Her hair is pulled back into a wavy ponytail that goes past her shoulders, but from the front, you cannot tell what length it is, a trick that pop starlets pull a lot, and a reminder that though this might be the height of her Country Career, the hair was no longer reaching for the skies, but practicing pop perfection.
Next: Number 4: 20145 Brit Awards
LONDON, ENGLAND – FEBRUARY 25: Taylor Swift attends the BRIT Awards 2015 at The O2 Arena on February 25, 2015 in London, England. (Photo by Samir Hussein/WireImage)
4. 2015 Brit Awards in Roberto Cavalli
Taylor Swift, Queen of Pop, Mother of Dragons. Because Dragons are in right now, thanks to Game of Thrones. (Though one might argue Dragons are never not in. Dragons are where they wish to be, and no one is allowed to say boo.) In this case, the dragon in question is riding across Taylor Swift’s back in this knock out Roberto Cavalli dress at the 2015 Brit Awards. It’s taking advantage of the dramatically shortened hair–a few years ago, Taylor would have needed a serious up do to remove the long length of curls she sported on a daily basis to show this creation off properly. Now there’s no need–the trendy hair keeps itself to itself, and far away from any fire the dragon might breathe. And this is a case where the very red lip is deployed properly, taking it’s shade cue from the dragon and tying the face to the long dragon’s tail that adorns the train. Daenerys Targaryen would approve, and perhaps have one commissioned for herself.
LOS ANGELES, CA – JANUARY 26: Recording artist Taylor Swift attends the 56th GRAMMY Awards at Staples Center on January 26, 2014 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
3. 2014 Grammys in Gucci Première
This is one of my personal favorite gowns of Taylor’s ever. In 2014, Taylor Swift wore armor to the Grammys. At first glance this Gucci Première feels like a throwback to an earlier style she had favored with her metallic and sparkle phase. At first glance, one might even say it was unsophisticated, with the causal ponytail and minimal make up. But those aren’t sequins or silver threads. This is a column of chain-mail from head to foot. She could walk into battle wearing this gown and walk out unscathed. Even her platform shoes are easy to hand weaponry. With 1989 only weeks from coming out, and Swift feeling under siege from a momentary (though perhaps not all that unexpected) backlash, this is the perfect way to keep the hounds like Ryan Seacrest at bay. All that and it photographs spectacularly too.
Next: Number 3: 2011 Wonderstruck
Wonderstruck Ad Campaign, 2011. Elizabeth Arden / Taylor Swift Wonderstruck fragrance (Dress: Christian Siriano. Art Directors: Eugenio Recuenco and Eric Dover)
2. 2011 Wonderstruck Ad Campaign in Christian Siriano
It’s always a moment when designer and muse come together at the same place at the same time going in the same direction. Christian Siriano, who designed this amazing floating princess dream of a gown for Taylor’s 2011 Wonderstruck perfume campaign, was exactly in the same place as Taylor when it came to his aesthetic. The most successful of the Project Runway winners alumni club, Siriano made his career on fantasy gowns for the girliest of girls, and though nowadays he’s reaching farther afeild in 2011 this was right smack in the middle of his lane, as it was Taylor’s as well. A perfect match created one of Taylor’s most amazing moments on celluloid, and one of her most memorable and most beautiful moments of her career to date.
NEW YORK, NY – MAY 05: Taylor Swift attends the “Charles James: Beyond Fashion” Costume Institute Gala at the Metropolitan Museum of Art on May 5, 2014 in New York City. (Photo by Kevin Mazur/WireImage)
1. 2014 Met Gala in Oscar de la Renta
Hands down the best she’s ever looked. Vintage is Taylor Swift’s fashion wheelhouse, a fact she’s been slowly copping to as she grows older. So when the theme for the 2014 Met Gala was announced as Charles James, the famous 1950s designer, it was one of those no brainer moments. Other years she might have done better to avoid the theme algether, but ehre it was like they had made on just for her. Much like the pale pink gown was just for her. Custom designed by the late Oscar De La Renta, it was one of the last dresses he designed before he passed later that year. He blessed her with one of her most sophisticated looks ever. Then of course, there’s the train, which stretched out from the bow at the back, made a good impact in photos on the Met staircase. The flat ironed hair adds to the 1950s retro vibe, as does the make up with the waning days of her signature red lip. It’s one of my personal favorite dresses Taylor Swift has ever worn.