Ever since she burst onto the scene in 2006, Taylor Swift has taken over the music industry (and fans’ hearts) with songs, albums, music videos, and so much more. Not a week has gone by without jamming out to classics like “Teardrops On My Guitar” and newer records like “Snow on the Beach,” and this year—with the Eras Tour, the accompanying concert film, and Taylor’s Version re-records of Speak Now and 1989 all in play—just may be the biggest yet. While the musician started out with her iconic curly locks and cowboy boots, her style has evolved with each era and we’ve since seen her rock matching sets, blazers, and more. While her red carpet looks always steal the show, we’re especially enamored with her street style looks, which show a more casual, wearable take on how her taste has evolved. Interested in doing a deep dive with us? Keep reading to see 35 of the most iconic Taylor Swift street style outfits of all time.
“Saturday Night Live” Afterparty (2023)
Swift and Travis Kelce have been making major headlines lately, and we love the outfit the star was serving at the “SNL” afterparty. The long gray trench from Gant took center stage atop a black Versace corset, and for accessories, she opted for a handbag from celeb-favorite brand Aupen, black and gold Greymer heels, and Maria Tash jewelry.
New York City Street Style (2023)
On an unseasonably warm day, Swift adapted her always-strong fall style by pairing an oversized black quarter-zip with brown knee-high boots. She completed the look with a brown shoulder bag and a hint of red lipstick.
Kansas City Chiefs Game (2023)
We’re getting Reputation-era vibes with this ensemble Swift wore to a recent Chiefs game. She wore Area denim cutoffs with crystal embellishments plus leather knee-high Christian Louboutin boots, showing her ability to make a statement without being too over-the-top. She finished the look with a Logan Hollowell chain necklace and a leather shacket from Gant, giving a subtle nod to the outfit-sandwiching trend.
Recording Studio Session (2023)
During a visit to Electric Lady Studios in early October 2023, Swift showed off her own version of model-off-duty style (musician-off-tour style?) in this casual yet expertly styled look. She paired a graphic tee with bike shorts, then took the outfit to the next level with a hard-sided Louis Vuitton bag, New Balance sneakers, sunglasses, and a baseball cap.
New York City Street Style (2023)
Out to dinner recently with Sophie Turner and a whole crew of friends, Swift elevated a pair of baggy gray trousers for evening by pairing them with a black boat-neck top, a top handle bag, and open-toe heels. Classic jewelry and red lipstick completed the look.
VMAs Afterparty (2023)
Unexpected denim has been having a moment lately, and Swift embraced the trend in this pleated, corset-style minidress by EB Denim that she wore to the VMAs afterparty. A sparkly silver bag, open-toed heels, and layered jewelry completed the understated yet glam look.
New York City Street Style (2023)
During days off from the Eras Tour in summer 2023, Swift’s street style was on point, and this white eyelet Ralph Lauren set creates a fresh look that would work for any season, depending on the accessories. To create a warm-weather appropriate look, she opted for a minimalist brown leather Mansur Gavriel bag and strappy leather Aeyde sandals. For a pop of color, we love her earrings from Larkspur & Hawk.
Recording Studio Session (2023)
Another baseball cap moment from the music icon, Swift dressed down a classic pinstriped button-down during an early summer recording session. She wore the shirt loose and untucked with a relaxed baby blue mini skirt, a gray shoulder bag, the navy cap, and she even brought back her once-go-to oxfords (more on that later).
Upper West Side Stroll (2022)
Swift loves a matching set, and this tailored pinstripe moment from Max Mara is unforgettable. She wore this ensemble on the Upper West Side while rocking her signature red lip, and she tied in the red with loafer-style Prada pumps.
“Saturday Night Live” Afterparty (2021)
Swift and Blake Lively have been best friends for years, so it’s no surprise they attended the “SNL” afterparty together in 2021 following the release of Red (Taylor’s Version). For Swift’s outfit of choice, she opted for an Anine Bing double-breasted houndstooth blazer, black pants, a Vince Camuto bag, and a black silk face mask.
Sundance Film Festival (2020)
In 2020, Swift attended the Sundance Film Festival in a full houndstooth ensemble, and we’re here for it. To lean into the iconic pattern, she paired show-stopping knee-high Manolo Blahnik boots with a matching top, pants, and jacket set from Carmen March.
Gigi Hadid’s Birthday Party (2019)
Swift loves to mix and match high-end and affordable pieces, and that’s exactly what she did at Gigi Hadid’s birthday party in 2019. Her checkered Mango blazer was all the rage that year among everyone from Diane Kruger to Lucy Boynton, and the star paired hers with a floral dress from Zimmermann. She also put her love for cats on full display with a printed bag from Anya Hindmarch.
New York City Street Style (2018)
Walking around the streets of Tribeca, Swift wore a casual summer ‘fit that’s easy to recreate with pieces you likely already have in your closet. She paired a classic white button-down shirt with Gucci cut-off shorts, and for shoes, she chose heeled Tod’s booties with red and white stitching. Her black Tommy Hilfiger clutch pulls the entire outfit together, but we keep coming back to the cat earrings from Miu Miu, which are quintessentially Taylor.
“Saturday Night Live” Afterparty (2017)
Swift turns to Prada time and time again for accessories, and she looked powerful in these combat boots from the brand at the “SNL” afterparty in 2017. The specific style is no longer in production. She also wore an oversized bomber jacket, and the all-black outfit proves the classic color will always be in, no matter the season.
New York City Street Style (2016)
In 2016, Swift stepped out rocking a chic, monochromatic ensemble for a night out on the town in Manhattan. She paired a black Aritzia bodysuit with a darling white mini skirt, and we love how it looks with her strappy Louise Et Cie heels and Aspinal of London hard-sided clutch. If you remember 2016, you’ll recall how popular chokers were, and her crystal necklace from Adornmonde truly makes the look.
Los Angeles Street Style (2015)
If you look closely, you might notice that Swift’s dress spells her name. And yes… it’s indeed a dress, albeit styled in “baseball” fashion. It might not be everyone’s cup of tea, but we love that she’s been a style risk-taker over her years in the spotlight. This dress was part of a collection exclusively available in China at the time, and we love how she styled it with heeled sandals from Stuart Weitzman. Her bag was from Elizabeth & James, the now-discontinued brand by Mary Kate and Ashley Olsen.
Los Angeles Street Style (2015)
There’s a lot going on in this outfit Swift wore while hanging out with Selena Gomez in 2015—but hear us out. This was the epitome of fashion during that time, and Swift nailed all the trends in one ensemble. She paired a “This Is My Fight Song” graphic tank (graphic shirts were a go-to for her during the early 2010s) with a Free People harness, and to finish off the look, she went with brown booties, sunnies, and a Louis Vuitton handbag that’s currently available on Rebag.
New York City Street Style (2014)
While we love Swift’s summer outfits, nothing beats her winter wardrobe. Her statement bright blue ASOS coat, which she styled with a white beanie and classic red lipstick, is something we’d absolutely wear today. For the bag, she once again turned to Prada, which is a designer she’s been spotted wearing tons of over the years.
London Street Style (2014)
We don’t know if this quite qualifies as outfit sandwiching, but Swift’s hot pink Giuseppe Zanotti heels and matching lipstick provided a fun pop of color against a neutral matching sweater set from Tanya Taylor.
New York City Street Style (2014)
Swift emphasized her long legs while out and about in SoHo in 2014. The hero piece of this look is a pair of high-waisted black-and-white shorts, which she styled with a black long-sleeve crop top from Aritzia, ankle boots, and a forest green leather bag.
New York City Street Style (2013)
Oxfords used to be Swift’s favorite fall and winter shoe choice, and here, she paired them with a classic pair of Wayfarers from Ray-Ban and a large brown leather shoulder bag. As for the outfit itself, she opted for a pair of maroon skinny jeans and a black sweater.
New York City Street Style (2012)
Swift is wearing the same pair of oxfords in this photo from 2012, and we love the cozy way she styled them for winter. Back then, beanies were the winter accessory, and she paired a maroon version with dark green skinny jeans from Mother Denim, a polka-dot blouse, and a navy blue tailored coat. While she opted to wear several colors in one outfit here, they all come together seamlessly.
Arriving in Narita, Japan (2012)
Arriving in Japan in 2012, Swift looked impressively put-together after getting off a long flight. She paired a classic and cozy Ralph Lauren blue cable knit sweater with some jodhpurs featuring inner knee patches. For the bag, she went with her then-favorite leather satchel, which we imagine is great for holding travel essentials.
London Street Style (2012)
Again in her go-to pair of oxfords, Swift strolled through London in 2012 in a winter-friendly outfit. She made a mini dress cold-weather-friendly by layering it over black leggings, then completed the outfit with a leather satchel and dark gray scarf. The ensemble was very much with the times and a general outfit formula that many of us used to recreate.
New York City Street Style (2011)
Swift served a color blocking moment while walking the streets of New York in a pleated, mustard yellow skirt from Modcloth, pairing it with a simple navy blue sweater. The music artist added even more color with a pop of scarlet red heels and a blue Fendi bag, and we’d be remiss not to mention the hand-drawn 13 on her hand, which she used to do a lot in the early 2010s.
London Street Style (2011)
Back when striped tees were the cool-girl wardrobe must-have, Swift went shopping on London’s Portobello Road in the staple. She styled it with a black blazer and dark skinny jeans, giving off a subtle punk-rock vibe. For the accessories, she went with brown oxfords, a brown leather bag, and a navy blue beanie. And again—notice the 13 on her hand.
London Street Style (2011)
Swift looked effortlessly put-together while leaving her hotel in London in 2011. The oversized cream sweater here has billowing sleeves that, when layered atop a blue floral dress, create an elevated bohemian silhouette. She went with a simple long gold pendant necklace to tie everything together.
New York City Street Style (2010)
It’s not often that Swift has worn Betsey Johnson, but back in 2010, she embraced a ’40s-style frock from the designer in a pink-and-green floral print that’s a statement on its own. She finished off the look with a simple Ralph Lauren crossbody bag.
Paris Street Style (2010)
This full black-on-black look is timeless, and Swift used it to channel the Parisian aesthetic while out and about in the beautiful French capital. She tucked black skinny jeans into black leather riding boots with silver hardware, exaggerating the silhouette of her long legs. For the rest of the outfit, she chose a black tee, a blazer, and a brown leather purse.
New York City Street Style (2010)
Swift was in her original Speak Now era back in 2010, and the vibes were immaculate. While shopping in NYC, she opted for a boho white dress, which she paired with black T-strap sandals from American Eagle. Her bag choice from Gerard Darel is larger than life and has a fun floral pattern.
Arriving in Japan (2010)
Fresh off a plane in Japan in 2010, Swift exited the airport in a casual travel ensemble. She layered a striped cardigan over a black mini dress and sheer black tights, also carrying a ginormous brown leather bag and—in true Taylor fashion—rocking some brown cowboy boots.
London Street Style (2009)
Swift loves a red moment, whether it’s her iconic lipstick or a pop of color in her outfits. Here, she wore a red plaid mini dress with a black coat, which she styled with black tights and a pair of heeled lace-up Christian Louboutin boots.
London Street Style (2009)
With her lucky number 13 printed on her hand, Swift walked around the streets of London in 2009 in a youthful ensemble. The star went with black leggings and knee-high boots for the bottom half of her outfit, and on top, she opted for a graphic tee from Topshop layered underneath a black leather jacket.
“The Late Show with David Letterman” Appearance (2008)
In 2008 Swift made an appearance on “The Late Show with David Letterman” in a fun, printed skirt from French Connection. She took it a step further with lacy tights, then kept the rest of the look simple with a black sweater and layered brown bracelets.
MTV Studios Visit (2008)
If you’ve been a Swiftie since day one, you’ll recall her love for cowboy boots dated all the way back to the beginning. Here, she wears a pair from Corral, which she styled with black skinny jeans, an oversized black coat, and a gray beanie.
