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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How to Rewear Your Taylor Swift Eras Tour Clothing IRL

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

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June 29, 2023

Taylor Swift in a floral top, black denim jeans, and sling-backs

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The songstress beat the heat in a floral tank, black denim shorts, and classic black sling-backs. Her accessory du jour? Tortoise-shell cat-eye sunglasses.

02of 100

June 27, 2023

Taylor Swift in a white eyelet blouse and jean skort

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Nothing says summer like a white eyelet top. Here, Swift pairs hers with chunky loafers and on-trend denim bottoms (ICYMI: The skort has made a comeback).

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03of 100

June 26, 2023

Taylor Swift in a baseball cap, striped dress shirt, and tennis skirt

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In New York City, Swift resembled an off-duty schoolgirl embracing summer. She topped off her pinstriped button-down by The Row and Free People skort with a navy baseball cap and Malone Souliers chunky oxfords-sock-combo.

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May 24, 2023

Taylor Swift in a white eyelet top and skirt

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Swift stepped out in Ralph Lauren all-white summery separates and neutral accessories — a Mansur Gavriel leather bag and strappy sandals, to be exact — as she headed to Electric Lady Studios in Greenwich Village.

05of 100

May 22, 2023

Taylor Swift in a white button-down shirt and black destroyed shorts

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Swift made a stylish appearance in New York City wearing a simple white button-down and black distressed denim shorts that read as casual sophistication.

06of 100

June 11, 2022

Taylor Swift wearing a pinstriped navy vest and suit pants

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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.

07of 100

January 23, 2020

Taylor Swift in head-to-toe gray, black, and white plaid

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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.

08of 100

October 6, 2019

Joe Alwyn with Taylor Swift who is in a black coat and black pants with colorful sequins

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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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09of 100

April 22, 2019

Taylor Swift wearing a red checked coat, floral skirt, and graphic cat bag

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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.

10of 100

July 22, 2018

Taylor Swift in an oversided white button-down, destroyed denim shorts, and booties

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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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11of 100

July 20, 2018

Taylor Swift wearing a leopard mini skirt, and a sheer, black, lace top with studded sandals

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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.

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July 18, 2018

Taylor Swift in a cropped denim top and black denim shorts

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

13of 100

October 23, 2016

Taylor Swift in a black bandeau top and high-slit skirt

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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.

14of 100

September 28, 2016

Taylor Swift in a plaid shirt, black skinny jeans, and Gucci loafers

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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.

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September 27, 2016

Taylor Swift in a black mini dress and trench coat

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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

Taylor Swift in a multicolored striped top and purple mini skirt

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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.

17of 100

September 14, 2016

Taylor Swift in a black and white striped minidress and loafers

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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.

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July 14, 2016

Taylor Swift wearing overall shorts and a white sleeve shirt with sneakers

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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

Taylor Swift in a printed wrap dress

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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.

20of 100

July 6, 2016

 Tom Hiddleston with Taylor Swift wearing a navy knit pullover, plaid skirt, and oxfords

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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.

21of 100

June 28, 2016

Taylor Swift in a light yellow top, white skinny jeans, and gray suede sandals with Tom Hiddleston

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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.

22of 100

June 21, 2016

Taylor Swift wearing a red crop top and maxi skirt with Tim Hiddleston

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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.

23of 100

May 12, 2016

Taylor Swift in a black to and leopard print mini skirt

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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.

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May 1, 2016

Taylor Swift in a plaid dress and black jacket

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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.

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April 30, 2016

Taylor Swift in a black lace Haney jumpsuit

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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

Taylor Swift in denim shorts, a black t-shirt, and white sneakers

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

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April 6, 2016

Taylor Swift in a belted black dress with Calvin Harris

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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

Taylor Swift in an all-white outfit with crop top

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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.

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February 24, 2016

Taylor Swift in a black t-shirt dress and chunky boots

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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.

30of 100

December 13, 2015

Taylor Swift in a plaid miniskirt, cropped navy sweater, and stockings

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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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31of 100

October 7, 2015

Taylor Swift in high-waisted black skinny jeans, a ribbed turtleneck, and booties

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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.

32of 100

July 13, 2015

Taylor Swift in a pink lace dress and flower crown

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

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June 10, 2015

Taylor Swift in a white crop top, flirty skirt, and sandals

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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

Taylor Swift wearing a floral skirt and cropped knotted top

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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.

35of 100

May 28, 2015

Taylor Swift in tight black overalls and a white crop top

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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.

36of 100

May 27, 2015

Taylor Swift in a white top and shorts with a nude handbag and turquoise pumps

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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

Taylor Swift in a navy tank, high-waist printed shorts, and turquoise pumps

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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.

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May 8, 2015

Taylor Swift in Alice + Olivia shorts with a black top, Charlotte Olympia crossbody, and Prada booties

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

39of 100

May 2, 2015

Taylor Swift wearing a little black dress, Louis Vuitton monogram bag, and Asos platforms

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

40of 100

April 18, 2015

Taylor Swift in a matching set with pointed green shoes and bag

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

41of 100

April 18, 2015

Taylor Swift wearing a powder blue minidress, mustard yellow bag, peach kitten heels, and a headband

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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.

42of 100

March 30, 2015

Taylor Swift wearing a black paneled crop top, white pleated skirt, and heart-stamped purse

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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.

43of 100

February 4, 2015

Taylor Swift wearing a black bowler hat, shirt, skort, and chunky platform sandals

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The singer stepped out in L.A. 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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44of 100

January 19, 2015

Taylor Swift in a plaid wool coat over a teal top and Brandy Melville corduroy skirt

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Swift hit the N.Y.C. 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.

45of 100

January 17, 2015

Taylor Swift in a red double-breasted coat with knee-high boots

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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.

46of 100

December 26, 2014

Taylor Swift wearing black skinny jeans, boots, and a leather jacket

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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

Taylor Swift in a powder blue coat, sheer black stockings, and sparkly headband

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

48of 100

December 22, 2014

Taylor Swift in a Mackintosh toggle coat,, plaid skirt, maroon tights, and oxford heels

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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.

49of 100

December 12, 2014

Taylor Swift in an Oscar de la Renta frock, Christian Louboutin heels, and a sleek black topper

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

50of 100

December 1, 2014

Taylor Swift in black lace top, red plaid skirt, and patterned tights

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

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November 23, 2014

Taylor Swift in a graphic tee and gray plaid skirt

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For a jaunt in L.A., 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

Taylor Swift wearing a navy and white sweater, burgundy pants, and knee-high boots

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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.

53of 100

November 4, 2014

Taylor Swift wearing a checked Miss Patina collared dress and an oxblood Aldo top handle bag

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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.

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October 27, 2014

Taylor Swift in a graphic top and pencil skirt with turquoise platform pumps

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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

Taylor Swift in a Miss Patina button-down top with Everlane shorts, oxford pumps, and knee-highs

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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.

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October 12, 2014

Taylor Swift wearing a burgundy 525 America sweater layered over a gray top and tights

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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.

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October 10, 2014

Taylor Swift wearing skinny khaki pants, flats, and a bright pink stop

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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

Taylor Swift in a Novis swing coat worn over Timo Weiland separates

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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.

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October 8, 2014

Taylor Swift wearing a Tanya Taylor sweater and skirt with pink heels

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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.

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October 7, 2014

Taylor Swift wearing a trench coat

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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

Taylor Swift wearing a burgundy plaid coat

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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.

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October 3, 2014

Taylor Swift in a flirty black Erin Fetherston frock and metallic heels

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

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September 16, 2014

Taylor Swift in a plaid skirt, white long-sleeve tee, burgundy thigh-high stockings, black heeled loafers, and a forest green handbag

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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.

100 Reasons Why Taylor Swift Is a Street Style Pro

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September 15, 2014

Taylor Swift in a matching set by Aqua and hot pink Christian Louboutin peep-toe pumps

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

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September 3, 2014

Taylor Swift in a black top and flared skirt with blush pink handbag

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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.

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August 13, 2014

Taylor Swift in a black-and-white Jonathan Simkhai peplum croc dress

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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.

Street Style

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August 12, 2014

Taylor Swift in a floral and stripe print top and skirt with metallic pink and mesh-paneled pumps

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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.

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August 6, 2014

Taylor Swift in a teal patterned crop top, marigold yellow skirt, and platform boots

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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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July 31, 2014

Taylor Swift in a nautical navy and white stripe Topshop dress

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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.

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July 30, 2014

Taylor Swift wearing a sheer, dotted Novis dress layered over a matching cropped bustier top and skirt

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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.

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July 29, 2014

Taylor Swift wearing a tucked in striped button-down with a pair of coral shorts

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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

Taylor Swift wearing a matching Alice + Olivia crop top and skirt with bright pink Christian Louboutin pumps and a yellow Dolce & Gabbana bag

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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.

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July 22, 2014

Taylor Swift in printed mint green dress with pink peep-toe pumps

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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

Taylor Swift wearing a peach Alice + Olivia boxy crop top and trapeze skirt, Tod's handbag, and nude Prada heels

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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.

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July 14, 2014

Taylor Swift wearing a white tee, denim cutoff shorts, and nude pumps

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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

Taylor Swift in a black tube top, capris, and strappy heels

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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.

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July 7, 2014

Taylor Swift in a black-and-white polka dot bralette crop top and skirt combo

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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.

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July 2, 2014

Taylor Swift in a belted floral romper and mustard yellow pumps

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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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June 30, 2014

Taylor Swift in a white button-down tied in the front with gray-and-white floral-print capris

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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.

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June 20, 2014

Taylor Swift in a cheery floral Oscar de la Renta frock and green pumps

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

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June 19, 2014

Taylor Swift in an A.L.C. blouse, bright short shorts, and Oxford heels

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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.

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June 18, 2014

Taylor Swift in a matching pink and white crop top and skirt

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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.

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June 17, 2014

Taylor Swift in a blue shirt, black capris, and maroon pumps

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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

Taylor Swift wearing a black MinkPink crepe romper

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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.

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May 31, 2014

Taylor Swift in a floral print sundress and nude platform sandals

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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.

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May 4, 2014

Taylor Swift in a gingham-print top and pencil skirt

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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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