100 Reasons Why Taylor Swift Is a Street Style Pro

Taylor Swift is a global superstar with unparalleled musical talent, an impressive girl squad, and most importantly (or at least for the sake of this article), covetable street style.

And while we love seeing her dressed to the nines on the red carpet, there’s something wholesome and humbling about spotting Miss Americana out and about in off-duty gear — especially when her cat is involved.

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Keep scrolling for 100 of Taylor Swift’s best street-style moments.

June 11, 2022

Outside the Beacon Theatre in New York City, Swift stepped out in menswear — with a twist. Her pinstriped vest and pants sans shirt is the business casual look we’re excited to get behind.

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January 23, 2020

Usually, when we refer to monochrome outfits the focus is solely on color (or lack thereof). But here, Swift elevates your standard monochromatic look by embracing a head-to-toe pattern that we can’t get enough of.

October 6, 2019

Who could forget when Miss Americana was spotted out with then-boyfriend Joe Alwyn wearing coordinated black blazers? The couple’s outfits pulled at our heartstrings and almost had us convinced that they were a perfect match.

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April 22, 2019

Swift takes a turn from her signature synchronized style by opting for this eclectic ensemble instead: red checkered coat, floral skirt, and … graphic cat shoulder bag? Let’s just say it gives the cat lady name a whole new appeal.

July 22, 2018

Leaving her apartment in New York City, the It-girl wore a white button-down with destroyed denim shorts. It was the perfect mix of classic and cool.

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July 20, 2018

The star hit the streets in a sheer black lace top, leopard-print miniskirt, and studded sandals that had us saying, grr, baby, very grr.

July 18, 2018

She styled her blue denim crop top with black denim shorts and some fresh white kicks. It’s practical, yet stylish.

October 23, 2016

Swift stepped out for Drake’s 30th birthday party in L.A. in a black bandeau top and high-slit skirt that showed off her mile-long legs. She completed the look with a black Meshki duster trench coat, Christian Louboutin spiked heels, and a metallic box clutch.

September 28, 2016

Swift put her street style know-how to good use in a comfortable black, red, and white plaid shirt, coordinating her simple shirt with black skinny pants and a pair of black leather Gucci loafers.

September 27, 2016

Out in New York, she strutted the pavement in a leg-baring black minidress and a classic trench coat.

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September 16, 2016

Here, the blonde beauty wore a flirty purple miniskirt that she paired with a colorful striped long-sleeve top. She accessorized the fall-ready pieces with a pair of towering suede heels and a coordinating leather crossbody bag.

September 14, 2016

The pop princess looked poised and polished in a black and white striped minidress with burgundy Michael Kors loafers and a small baby blue bag while out in the Big Apple.

July 14, 2016

The singer-songwriter ventured out for a shopping trip in Australia wearing a casual uniform of overall shorts layered over a long-sleeve white tee. Paired with classic white sneakers, a small green cross-body bag, and an impeccable blowout, the star was all smiles as she headed out for a shopping spree on the country’s Gold Coast.

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July 10, 2016

The songstress heading into Gemelli Italian Restaurant for a romantic dinner with her date Tom Hiddleston. She accessorized her plunging wrap dress with suede lace-up sandals, a tan cross-body bag, and maroon stud earrings.

July 6, 2016

The couple was seen flying out of LAX in coordinating navy ensembles: Hiddleston wore a navy quilted jacket, dark jeans, and gray suede shoes, while Swift opted for a navy knit pullover over a short blue plaid skirt, and delicate cream and tan oxford flats with cutout details.

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June 28, 2016

While out in Rome with new boyfriend Tom Hiddleston, the singer wore a light yellow top, white cropped skinny jeans, a nude crossbody bag, and gray suede FL&L X Raye Myra heels.

Taylor Swift and Tom Hiddleston Step Out in Coordinating Looks17of 100June 21, 2016

The new couple attended Selena Gomez’s Nashville concert where they were spotted leaving the venue hand in hand. For their date night out, Swift wore a tight short-sleeve red crop top and coordinating maxi skirt, which she accessorized with a Rebecca Minkoff crossbody bag and black flats.

May 12, 2016

Swift stepped out in L.A. wearing high-waisted leopard print The Kooples short shorts, a black turtleneck, Alexander McQueen bag, and mesh Alaïa heels.

May 1, 2016

Swift was seen leaving Gala preparations sporting a flowy, asymmetrical plaid dress with a black leather jacket and a pair of black patent leather chunky-heeled boots.

April 30, 2016

The “Shake It Off” singer wore a black lace Haney jumpsuit with see-through long sleeves and pants out in New York City. She accessorized the outfit with a pair of black lace-up booties and a crisp cranberry lip.

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April 28, 2016

The singer rocked a pair of black denim shorts with a matching T-shirt and plain white sneakers.

April 6, 2016

Swift and boyfriend, Calvin Harris, were spotted heading to dinner at Giorgio Baldi in Santa Monica. The singer wore a black dress with matching heels and clutch, plus a bright red lip for a pop of color.

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February 24, 2016

Swift chose an all-white look for dinner with producer Jack Antonoff at Maia restaurant in West Hollywood. The singer wowed for the occasion in wide-leg pants, an Isabel Marant double-breasted blazer with gold buttons, and an ab-tastic crop top.

February 24, 2016

The “New Romantics” singer stepped out in Los Angeles for a quick shopping trip to the Isabel Marant Melrose boutique wearing a T-shirt dress by the designer, which she accessorized with platform boots and a Versace bag.

December 13, 2015

Swift strutted through LAX in a plaid mini skirt with an asymmetric hemline. A navy crop top sweater that revealed her bare midriff added a touch of warmth to the look.

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October 7, 2015

To hit the recording studio in N.Y.C., the songstress wore high-waisted black skinny jeans and a matching ribbed turtleneck, which she paired with heeled booties.

July 13, 2015

The “Bad Blood” singer sported a pink lace dress and matching gilded flower crown while stepping out of her Tribeca apartment in NYC.

June 10, 2015

Swift stepped out in New York City wearing a crop top and flirty skirt that she paired with sweet pale pink accessories.

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May 29, 2015

A Michael Kors floral skirt and knotted top were the singer’s pieces of choice for a girl’s night out in N.Y.C.

May 28, 2015

Taylor Swift jumped on the overalls trend, stepping out in an inky black slim-fit denim one-piece that she styled with a crop top (aka her go-to piece), a burgundy cross-body purse, and black booties.

May 27, 2015

Off to promote her 1989 World Tour-inspired Keds collection in N.Y.C, Swift stepped out in a structured white top and matching shorts. She accessorized the look with bright turquoise SJP Collection shoes and a neutral Michael Kors handbag.

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May 26, 2015

Swift exuded confidence in these high-waist graphic-print shorts styled with a navy sleeveless top, a glittery Mary Katrantzou purse, Swarovski shades, and aqua pumps.

May 8, 2015

For an outing in the Big Apple, Swift paired her Alice + Olivia shorts with a black top, Charlotte Olympia crossbody, and Prada heels.

May 2, 2015

Taylor showed off her chic airport style in a cute LBD, Louis Vuitton monogram bag, and Asos platforms.

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April 18, 2015

The star stepped out in a matching set by Missguided, which she paired with bright green Prada pumps and a matching Elie Saab bag.

April 18, 2015

The singer was spotted in New York City in a sugary sweet pastel ensemble that included a powder blue minidress, mustard yellow bag, peach kitten heels, and a headband.

March 30, 2015

Taylor Swift hit the town with friends in a black paneled crop top with a white pleated skater skirt. The finishing touches? A sweet heart-stamped purse, her signature red lip, and black peep-toes.

February 4, 2015

The singer stepped out in LA wearing a black origami-front Missguided skort that she styled with a loose black T-shirt, chunky Asos platform sandals, a Free People hat, and burgundy Cambridge Satchel bag.

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January 19, 2015

Swift hit the NYC streets with her cat Olivia Benson. She wore a Gestuz plaid wool coat over a teal top and Brandy Melville corduroy skirt. Finishing off her look, Swift opted for bordeaux suede booties by Rag & Bone and a black top-handle bag.

January 17, 2015

Swift channeled her inner equestrian by pairing a bright red Rachel Zoe peacoat with tan jodhpurs, knee-high boots, and a Gigi Burris Millinery cap for a Whole Foods run in N.Y.C.

December 26, 2014

Swift chose head-to-black for an outing in New York City, where she wore a J Brand leather jacket, dark skinnies, and Rag & Bone booties.

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December 24, 2014

The star hit the Big Apple streets in a chic powder blue coat, floral embroidered tights, a sparkling headband, and a bold fuchsia lip.

December 22, 2014

Swift took preppy to a new level in a Mackintosh toggle coat, navy Ralph Lauren turtleneck sweater, a plaid skirt, maroon tights, and Cole Haan oxfords.

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Swift left her apartment in NYC wearing a dreamy Oscar de la Renta frock, which she paired with Christian Louboutin heels and a sleek black topper.

December 1, 2014

Swift hit the streets of Londontown in a black lace Free People top, red plaid bottoms, patterned tights, and matching accessories.

November 23, 2014

For a jaunt in LA, the star added edge to her look in a graphic T-shirt and gray plaid RD Style skirt with black accessories.

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November 13, 2014

The singer looked festive in this navy sweater, burgundy skinny jeans, chic knee-high boots, and her favorite Aldo bag, all topped off with a green Topshop knitted beanie.

November 4, 2014

Swift arrived at the airport in Japan wearing a checked Miss Patina collared dress, which she accessorized with an oxblood Aldo top handle bag and & Other Stories chunky black heels.

October 27, 2014

Swift made her way out of Good Morning America in New York City rocking a matching graphic top and pencil skirt, which she paired with platform heels and her signature red lip.

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October 21, 2014

Swift showed off her cheeky side in a quirky Miss Patina button-down top with Everlane shorts, oxford pumps, and an Aldo handbag in Los Angeles.

October 12, 2014

Swift hit the streets of New York City wearing a burgundy 525 America sweater layered over a gray top and tights, which she styled with a selection of matching accessories including an Aldo bag and Jimmy Choo booties.

October 10, 2014

The singer added a pop of pink to her look in London in the form of a crewneck sweater worn with caramel-colored Joe’s jeans and Miu Miu jeweled flats.

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October 9, 2014

Swift mixed prints in a Novis swing coat worn over Timo Weiland separates in London, which she paired with a Rag & Bone hat, black tights, and Jimmy Choo ankle boots.

October 8, 2014

The star perfectly matched her pout to her Giuseppe Zanotti platforms while out in London, rocking a hot pink shade that brightened up her chic Tanya Taylor sweater and skirt combo. She completed the look with delicate Hysteric Co. jewels.

October 7, 2014

For an outing in Paris, Swift chose a seriously chic camel-colored trench coat worn over a zippered red A.L.C. top and skirt that she paired with black heels and a retro-style hairdo.

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October 6, 2014

The singer hit the streets of Paris in a white long-sleeve top and pleated BCBG MaxAzria A-line skirt worn under a burgundy plaid coat. She topped off her look with sleek Brian Atwood booties and a matching bag.

October 3, 2014

Swift stepped out in New York City in a flirty black Erin Fetherston frock and metallic Christian Louboutin heels.

September 16, 2014

Swift wore a plaid skirt, white long-sleeve tee, burgundy thigh-high stockings, black heeled loafers, and a forest green handbag for an outing with her adorable kitten, Olivia Benson.

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September 15, 2014

Swift made her way around New York City in a matching set by Aqua and hot pink Christian Louboutin peep-toe pumps.

September 14, 2014

The songstress stepped out in New York City wearing a reclaimed vintage floral matching set by Asos, which she paired with vibrant purple Brian Atwood pumps.

September 3, 2014

Swift hit the pavement in London wearing an chic matching set by Guess. She complemented the sultry pieces by elegantly styling them with her favorite blush Prada bag and strappy heeled sandals, creating a playful-yet-sexy look.

August 13, 2014

Swift switched things up and stepped out in an edgy black-and-white Jonathan Simkhai peplum croc dress, complete with her go-to blush pink Prada handbag and lace-up Bionda Castana pumps.

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August 12, 2014

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Swift paired her enviably adorable floral and stripe print H&M crop top and skirt with metallic pink and mesh-paneled pumps by Elie Saab, completing her look with black sunnies, favorite blush-hued Prada bag, and a selection of delicate jewels.

August 6, 2014

For an outing in New York City, Swift stuck to a ’70s color scheme in a teal patterned crop top, marigold yellow skirt, burgundy Max Mara bag, and Timberland platform boots.

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August 1, 2014

Swift made a stylish appearance in New York City wearing a black-and-white check gingham dress, lipstick red Hayden Lasher crocodile bag, and heeled oxfords.

July 31, 2014

Swift stepped out in New York City looking nautical and fresh in a navy and white stripe Topshop dress. She finished off her look with nude Saint Laurent shoes, a matching Prada bag, Ray Ban wayfarers, and her signature red lip.

July 30, 2014

The singer stepped out in New York City wearing a sheer, dotted Novis dress featuring an attached floral skirt that she layered over a matching cropped bustier top. She completed her look with metallic Christian Louboutin peep-toe pumps and a bright blue Bulgari bag.

July 29, 2014

Swift nailed her street style again with a menswear-inspired look. She tucked in a striped button-down into a pair of coral shorts, and styled them with her blush Dolce & Gabbana handbag and two-toned Oxfords.

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July 24, 2014

For a day out in New York City, Swift donned a matching Alice + Olivia crop top and skirt with bright pink Christian Louboutin pumps and a sunny yellow Dolce & Gabbana bag.

July 22, 2014

The musician stepped out in another one of her signature sweet looks, accessorizing her printed mint green dress with wayfarers, an “S” Lulu Frost necklace (in honor of BBF Selena Gomez’s birthday), her go-to nude Tod’s handbag, and fuchsia peep-toes.

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July 18, 2014

The country star hit the New York City streets wearing a peach Alice + Olivia boxy crop top and trapeze skirt, Tod’s handbag, and nude Prada heels.

July 16, 2014

Swift stepped out in New York City wearing a belted navy tunic dress, leather Rag & Bone ankle boots, and a black Dolce & Gabbana bag.

July 14, 2014

Swift hit the street in New York City wearing a white Theory tee, Black Orchid denim cutoff shorts, nude Prada pumps, and her favorite Dolce & Gabbana handbag.

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July 11, 2014

The singer looked impeccable in a sultry Reformation jumpsuit for an outing in New York City. She completed her all-black ensemble with a Dolce & Gabbana handbag, Christian Louboutin sandals, and a cherry red lip.

July 9, 2014

Swift stayed true to her retro-chic aesthetic with a pretty floral print button-down dress that she styled with a nude ladylike Tod’s handbag, a sweet hairpin, and nude Mary Jane sling-backs.

July 7, 2014

Swift stepped out in New York City in a black-and-white polka dot bralette crop top and skirt combo, which she styled with a green Kate Spade bag, retro heels, and her signature bold red lip.

July 2, 2014

Swift squeezed in another workout and was snapped leaving the gym in a bold floral-print button-down Reformation romper, cinching it at the waist with a brown belt. Suede goldenrod yellow Gucci pumps and her go-to Dolce & Gabbana tote completed her look.

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July 1, 2013

Swift welcomed the month of July in a retro-inspired white-and-yellow gingham print Miu Miu crop top and mint green skater skirt, which she paired with coral heels and her trusty Dolce & Gabbana handbag while out and about in New York City.

June 30, 2014

Swift left the gym looking impossibly chic and refreshed in a white button-down that she tied in the front, pairing it with gray-and-white floral-print capris, her go-to Dolce & Gabbana handbag, and nude high-heel sandals.

June 20, 2014

Swift stood out in a cheery floral Oscar de la Renta frock in NYC, further amping up the vibrancy with a Kelly green Elie Saab cross-body purse and matching pumps.

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June 19, 2014

Swift made a case for preppy summer attire in an A.L.C. blouse, bright short shorts, Oxford heels, and her trusty Dolce & Gabbana handbag.

June 18, 2014

Swift fended off the heat (and showed off her toned tummy in the process) in a matching skirt and crop top combo while out and about in New York City. She completed the outfit with nude sandals, a tan handbag, and red lipstick.

June 17, 2014

The singer was spotted leaving the gym in a ladylike ensemble of black leggings, a classic blue button-down, maroon pumps, and a Gelareh Mizrahi heart-shaped bag.

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June 14, 2014

The singer stepped out in New York City post-workout wearing a simple MinkPink crepe romper. She paired the summer-ready piece with a black circle bag, strappy peep-toe heels, and her signature bold red lip.

May 31, 2014

Swift arrived at Narita International Airport looking picture-perfect in a pretty floral print sundress, accessorizing it with an embellished braided headband, Red C Jewels, a Tod’s handbag, and strappy nude heels.

May 4, 2014

Swift was picture-perfect in ladylike separates, tucking a sculpted gingham-print top into a below-the-knee-length pencil. A boxy bright red cross-body purse and Oxford heels rounded out her look.

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May 2, 2014

The singer gave the “To Tommy, From Zooey” polka-dot-striped shirtdress her personal flair with a red bow-accented belt, a top-handle Dolce & Gabbana bag, and black Mary Janes.

April 29, 2014

Not even April showers can put a damper on Swift’s style, who was all smiles in a striped long-sleeve top, burgundy skinnies, a felt hat, and black Rag & Bone lace-ups.

April 28, 2014

Swift struck again in a retro-glam look, styling her vintage-inspired floral ModCloth dress with a forest green Elie Saab purse, a pearl hair barrette, and moss green loafer heels.

April 27, 2014

Swift was spotted with one of her BFFs (model Karlie Kloss) in a belted Michael Michael Kors indigo shirtdress, complete with her Dolce & Gabbana bag and black Oxford heels.

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April 26, 2014

Swift showed off her stems in a mini dress, layered under a moto style trench, and delicate ankle-strap sandals.

April 24, 2014

The musician channeled a throwback look reminiscent of the ’60s with a striped tee and a flirty gray A-line skirt, teaming them with a lovely yellow headband, her trusty Dolce & Gabbana handbag, and loafer heels.

April 23, 2014

Swift countered a flirty vibe with scalloped short shorts with preppy pieces, including a Rails blue button-down (with suede elbow patches!), burgundy knee-high socks that matched her fedora, and brown Oxford heels.

April 22, 2014

The singer looked garden party-ready in a blue-and-marigold yellow floral dress, color-matching the sunny hue with a floral headband. As for shoes, she selected green bow-topped Mary Janes.

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April 16, 2014

Swift wore her heart on her sleeve, or rather, all over, with a multicolored knit that she styled with a red cross-body purse, teal jeans, and aubergine brogues.

April 15, 2014

Swift ran errands in Soho, expertly matching her red purse to her colorful plaid top. Mint green AG skinnies and Oxford heels completed her look.

April 14, 2014

Swift sported one of her favorite silhouettes: high-waisted shorts. She paired them with a lace-collared top, an oversize cardigan, and two-toned Oxford heels.

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April 12, 2014

Swift embraced warmer weather in a striped top, cuffed Hudson denim shorts, statement red shades, and her favorite shoe type: Oxford heels.

April 10, 2014

Swift boasted a pretty pastel color palette, styling her blush pink Joe’s denim with a lemon-striped button-front, a nude Tod’s bag, and neutral pumps.

March 29, 2014

Out and about in New York City (with her kitty Meredith in tow), Swift pulled off mustard skinnies by coordinating them with a tucked-in blue Oxford and navy blazer with a yellow cross-body purse.