There's no segment of celebrity life that Taylor Swift hasn't conquered—from Easter eggs in her content to her deepening relationships with fans to her (oft-discussed) dating life. She gives us just enough to keep us interested, but we're always wanting more. Her street style is no exception: Over the course of her long career, she's had various "eras" to go along with her musical movements—from soft and feminine, to chic and business-like, to "fashion-girl" edgy. Swift is rarely afraid to try something new, and her everyday sartorial style is a real feast for the eyes.
Part of the basis of the appeal is Swift's "eye candy" (i.e., the person she's currently dating) or "gal pal" (the BFF she's going out with) that accompanies the outfit. Even when she knows that she'll be photographed, she does an impressive job of making all her street style sightings feel spontaneous—as if she's just like us, only cooler and better dressed. We usually catch glimpses of her out and about in New York (where she owns property), but we've also seen her edgy LA street style too and other formal events. Swift really kicked her street style into high gear in the 2020s, and her fashion-forward looks have been a blessing to witness.
Below, 32 of Taylor Swift's best street style outfits—this is just a smattering of many, many outfits to choose from. There are even Easter eggs in her outfit choices; I may not have spotted them all, so keep an eye out for them!
With Joe Alwyn in New York, 2019
The haphazard sparkles on Swift's Libertine trousers are a little unusual for the star—she tends to prefer patterns that are bigger and/or bolder—but it's actually her SNL performance look. Also, you can't fault her for matching with Joe Alwyn! They're wearing matching black oversized blazers, and the brown in her pants match the brown in his shoes.
With Selena Gomez in Los Angeles, 2015
I'm not...totally sold on the harness, but look at the cool graphic tee! Swift really loves "Fight Song," and she even had Rachel Platten (who released the debut single in 2015) perform the song with her during her 1989 tour. So this is a) a reference to Swift's adoration of the song, and b) a tour tie-in. Synergy!!
With Matt Healy in New York, 2023
Leaving aside the short-lived relationship with Matt Healy, Swift's fun choice of sweater—a vintage NYU shirt that fans went wild buying off the official store—was paired with a micro pleated miniskirt and tan flats. Per PopSugar, the Tod's bag is "a nod to her 2014 style when she notoriously sported the Italian brand's Stella tote." Always referencing!
In Los Angeles, 2016
Swift has magnificent taste in outerwear, and this edgy leopard-patterned coat is absolutely no exception. She paired the look with shorts—the better to show off her long, long legs—and impressively high platform sandals. As is often the case, she donned a red lip to take it over the top.
Attending the Republic Records MTV VMA 2022 Afterparty, New York, 2022
We don't always see the "graphic party outfit" look from Swift, but I really enjoy it—especially since she is literally a star. After taking home three awards, it was time to party in a shaggy white coat and Moschino mini romper(!) and glittery platform heels. Never, ever forget the red lip!
In New York, 2011
Ignoring the nude platforms (trendy at the time but now a bit dated), I really love this belted red dress. It felt like we really got an impressive style evolution from Swift in the '10s, where she really started to evolve from teen star into mega-mega-superstar adult.
In New York, 2012
Even though in her Red era Swift started going with blunter hairdos, edgier outfits, and a generally cool-girl style, she still opted for feminine pieces when headed to more formal events. With the gold sparkles in the dress perfectly matching her golden hair, Swift also trades her signature red lip with a softer mauve.
In New York, 2009
This mustard-y yellow Kate Spade coat (in a color she loves, with good reason) has enoooormous buttons in traditional '00s fashion. This is a sweet look at the star's early style: long, luscious wavy hair, a polished and feminine style, but still with a little personality—check out the patterned tights!
In New York, 2016
Now those are some tall sandals! (I could never, but she's rocking 'em effortlessly.) The pretty purple mini goes beautifully with the multicolored striped shirt—side note: is this the perfect fall outfit??—and brown suede peep-toe sandals, as well as the wine-colored lip she's blessed us with.
In New York, 2015
Swift moved to New York in 2015, and we started getting more sightings of the well-dressed star out and about. This was a particularly polished time for the star, and this color-blocked outfit, with pastel blue, yellow, and peach all in attendance, is no exception.
In New York, 2014
I'm always impressed at Swift's ability to look calm, cool, and composed—even when hordes of delighted fans are mere feet away from her. This fit and flare dress (which apparently was sold at Urban Outfitters and probably sold out in three seconds) was all the rage at the time.
In New York, 2023
The Taylor Swift of 2023 brought together trends and evolved her style in new and interesting ways. Take a floral red corset top, black denim shorts, chunky slingbacks, tortoise sunglasses, and a matching red lipstick, and you've got "Eras" Taylor Swift all the way.
In New York, 2023
Pulling from several 2020s trends—the wide leg pants, the baseball cap as fashion statement, the knit top, the slouchy shoulder bag, and the chunky boots—Swift also manages to make the look her own with some thin braids and a surprisingly nude lip color.
In New York, 2023
The 2000s pleated mini came back into fashion in the 2020s, and Swift jumped on board. Technically this looks to be a Free People skort, which combined with a The Row collared shirt is a nice high-low moment. Chunky Oxfords and a baseball cap kept things super-casual.
In New York, 2016
Never in my life will I ever be able to rock peep-toe booties like this! Swift wisely opts to keep things simple for the rest of the look: Simple black mini, tan trench, and pretty nude lip (I really need to figure out what makeup brand that is, because it's very cute).
In New York, 2014
I enjoy the posing here, with Swift glancing back as if she's about to head into a glamorous meeting, Sex and the City-style. This graphic black, brown, and white Jonathan Simkhai dress was a departure from her style at the time—although she has long loved that pink Prada bag.
With Keleigh Sperry in New York, 2023
This is a very-Princess Diana-esque take on athleisure, and it's super-fun. Swift sports a Shania Twain graphic tee, exercise shorts, and low sneakers on the way to a studio recording session. If you didn't know, her pal Keleigh Sperry (pictured) also starred in the music video of "Taylor Swift: I Bet You Think About Me (Taylor's Version)."
In New York, 2023
Swift, on the way to support Travis Kelce at a football game, is sporting a fun leather-on-leather look. The Christian Louboutin red-bottom heels (a rewear!) matching the red lip is a nice touch, but the standout is the bedazzled Area shorts that actually have a cutout at the lower back.
In New York, 2014
Actually, this might be the most fall outfit of all time (even though this photo was taken in spring). Plum-colored pants, an upscale tan short coat, plaid scarf and top, brown boots, black bag, and (of course) red lip: a classic matchy-matchy mid-10s Taylor Swift look.
With Gracie Abrams in New York, 2023
Swift and Gracie Abrams performed “I Miss You, I’m Sorry” live during the Eras Tour in 2023 (and Abrams opened for Swift on the same tour). This pic was taken after both were nominated for 2024 Grammys; The two pals are stylish, both in chunky loafers and Swift in a white dress and navy jacket.
In New York, 2023
Swift loooooves a mini. So this black Stella McCartney tunic dress is right up her alley. On the way to celebrate the re-release of 1989 (Taylor’s Version) with friends like Blake Lively and Ryan Reynolds, nbd, she also wore a Tod's crossbody and Prada boots—according to fans, a rewear!
In New York, 2015
Swift's nighttime looks are always really, really polished. See also: This tan coat, striped and polka-dotted tights (she loves polka dots, and this is fun and subtle) and Louboutin booties. According to fan sites, she was having dinner with Kanye West; Frankly, this is a great dinner outfit.
In Los Angeles, 2014
Lest anyone be laboring under the impression that "modern-polished" Taylor Swift is a recent thing, just know she was out here looking cute all the way back in 2014. As is standard for her, the red Oxfords match her red lip, and the whole thing feels like "I'm on the way to a meeting, cool girls only."
In New York, 2022
What do you wear when strolling around the Upper West Side? Pinstripe separates, of course! Loving the trademark Swift red shoes (Prada pumps) and red lip, but nothing's cooler than a Max Mara vest and trousers. Swift even cheerfully waved to fans as she exited the car.
In New York, 2023
A matching set in summer is the cutest way to stay cool. On her days off from touring, Swift sported this Ralph Lauren top and skirt. She kept things neutral in her bag and shoes, and then added a pop of color with blue Larkspur & Hawk earrings—and red lip, natch.
In New York, 2023
Swift shows us all that the skort, once thought to be a style for 8-year-olds, is now an item of clothing for adults too! (And they're quite comfy!!) Yellow bag, yellow shoes, white lacy Doên top, Free People skort: Swift made waves for her super-stylish summer outfit.
At the 2020 Sundance Film Festival, Park City, Utah
Ooooo head-to-toe houndstooth! In case you're curious, these are Manolo Blahnik boots and Carmen March top, pants, and jacket set. Usually, tonal dressing is all one color, often neutral but sometimes bolder. Somehow Swift pulls off the seemingly impossible—all-over pattern dressing.
In New York, 2021
I cannot help but love this purple velvet Etro suit. This is technically red carpet as much as it is street style, as Swift was there to promote her All Too Well: The Short Film. So as not to compete with the richness of the color, she wears a pretty pink lip (she took her mask off when she got inside).
With Tom Hiddleston in LA, 2016
When Swift dated Tom Hiddleston in 2016, it immediately became iconic amongst fans, dubbing the relationship "HiddleSwift." Fans got a few glimpses at their stylish pairing; Here, Hiddleston's blue jacket matches with her sweater and plaid mini (gotta love that LV bag, too).
With Sophie Turner in New York, 2023
Without ever having to say a word to the press, Swift showed support for her pal Sophie Turner, in the midst of a contentious divorce with Joe Jonas, by taking her out to dinner. The simple act proved wildly popular, and Turner and Swift were spotted again with a group of girls (including Selena Gomez). Love the thigh high boots and plaid mini, too.
With Travis Kelce at the 'SNL' Afterparty, New York, 2023
Fans may have never been more excited than after hearing about Taylor Swift's relationship with Travis Kelce. Here, at the SNL afterparty, the two aren't exactly matching, per se, but still look great together (Swift is in a Versace corset top and gray plaid Gant trench coat, if you're curious).
With Travis Kelce in New York, 2023
Kelce and Swift are wearing pretty different outfits here (I suppose you could argue that his black tee matches with her outfit), but for their date night they still look ultra-cute here, with Swift in a sheer print Jean Paul Gaultier top and brown mini and black boots from Louis Vuitton. Chef's kiss.
