Celebrity 100 Reasons Why Taylor Swift Is a Street Style Pro By Kelsey Glein Published on January 21, 2015 Pin Share Tweet Email Photo: Christopher Peterson/Splash News There's no doubt that Taylor Swift really does love her cats! The singer was snapped leaving her New York City apartment this week with one of her adorable pets in tow, and sporting one stylish outfit to boot. While this wasn't the first time we've seen Taylor toting her feline friend on the streets, it was the first time we've spotted her using one of her new personalized cat carriers. Taylor Swift Sports an Equestrian-Inspired Ensemble For the outing, Swift donned a Gestuz plaid wool coat over a teal top and Brandy Melville corduroy skirt, ($26), which she paired with bordeaux suede booties by Rag & Bone ($300) and a black top-handle bag. But the most eye-catching addition to her look was the red duffel, which housed her cat, Detective Olivia Benson. The embroidered carriers were actually a Christmas gift from Swift's mom—and she has one for each of her famous kitties. Check out the photo Swift shared of the set on Instagram below. http://instagram.com/p/xFiG7BDvLu/?modal=true PHOTOS: Taylor Swift's 68 Best Street Style Looks 01 of 100 October 23, 2016 AKM-GSI 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 ($68), Christian Louboutin spiked heels ($1,095), and a metallic box clutch. 02 of 100 September 28, 2016 Gardiner Anderson/Bauer-Griffin/GC Images 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. 03 of 100 September 27, 2016 Felipe Ramales/Splash News Swift stepped out in N.Y.C. on Tuesday in a leg-baring black minidress and a classic trench coat. 04 of 100 September 16, 2016 Alo Ceballos/GC Images For an outing in N.Y.C., the blonde beauty showed off her mile-long legs in a flirty purple mini skirt 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. 05 of 100 September 14, 2016 AKM-GSI 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 New York City. 06 of 100 July 14, 2016 AKM-GSI The singer-songwriter ventured out for a shopping trip in Australia wearing a casual uniform of overall shorts ($25) 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. 07 of 100 July 10, 2016 Splash News The songstress was out on Australia's Gold Coast heading into Gemelli Italian Restaurant for a romantic dinner with her Tom Hiddleston. She accessorized her plunging wrap dress with suede lace-up sandals, a tan cross-body bag, and maroon stud earrings. 08 of 100 July 6, 2016 Stoianov/FAMEFLYNET PICTURES The couple were 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. 09 of 100 June 28, 2016 Agostino Fabio/Splash News 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. 10 of 100 June 21, 2016 TheImageDirect.com 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 ($295) and black flats. 11 of 100 May 12, 2016 Maciel/AKM-GSI 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. 12 of 100 May 1, 2016 Raymond Hall/GC Images 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. 13 of 100 April 30, 2016 TheImageDirect.com 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. 14 of 100 April 28, 2016 Poersch / SPOT / AKM-GSI The singer rocked a pair of black denim shorts with a matching T-shirt and plain white sneakers. 15 of 100 April 6, 2016 AKM-GSI Swift and Harris were spotted heading to dinner at Giorgio Baldi in Santa Monica, Calif., and they couldn't have looked happier. The singer wore a black dress with matching heels and clutch and a bright red lip. 16 of 100 March 1, 2016 X17online.com Swift showed off her long legs in a black mini and strappy heels while out on a date in L.A. with boyfriend, Calvin Harris. 17 of 100 February 24, 2016 AKM-GSI 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. 18 of 100 February 24, 2016 TrickyD/FAMEFLYNET PICTURES 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. 19 of 100 February 21, 2016 Robert Kamau/GC Images Swift wore a chic black jumpsuit for the casual get-together and dinner with friend Lena Dunham and she accessorized the piece with a pair of pointy black pumps and a Prada handbag. 20 of 100 December 13, 2015 GVK/Bauer-Griffin/Getty Images 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. 21 of 100 November 17, 2015 AKM-GSI After dining out in Beverly Hills, the "Shake it Off" singer looked chic in an all black ensemble of leggings and a leather jacket with shawl collar. 22 of 100 October 7, 2015 Josiah Kamau/BuzzFoto via Getty Images 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. 23 of 100 July 13, 2015 Josiah Kamau/BuzzFoto via Getty Images The "Bad Blood" singer sported a pink lace dress and matching gilded flower crown while stepping out of her Tribeca apartment in NYC. 24 of 100 June 10, 2015 Papjuice/Bauer-Griffin Swift stepped out in New York City wearing a crop top and flirty skirt that she paired with sweet pale pink accessories. 25 of 100 May 30, 2015 James Devaney/GC Images The star hit the streets in short-shorts, platforms, a striped top, and cool shades. 26 of 100 May 29, 2015 NCP/Star Max 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. 27 of 100 May 28, 2015 Alessio Botticelli/GC Images 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. 28 of 100 May 27, 2015 Alessio Botticelli/GC Images 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. 29 of 100 May 26, 2015 GC Images Swift showed off her enviably long legs in NYC wearing a pair of high-waist graphic-print shorts that she styled with a navy sleeveless top, a glittery Mary Katrantzou purse, Swarovski shades, and aqua pumps. 30 of 100 May 8, 2015 GC Images For an outing in the Big Apple, Swift paired her Alice + Olivia shorts with a black top, Charlotte Olympia crossbody, and Prada heels. 31 of 100 May 2, 2015 FameFlynet Taylor showed off her chic airport style in a cute LBD, Louis Vuitton mongram bag, and Asos platforms. 32 of 100 April 18, 2015 NCP/Star Max/GC Images The star stepped out in a matching set by Missguided, which she paired with bright green Prada pumps and a matching Elie Saab bag. 33 of 100 April 18, 2015 Raymond Hall/GC Images 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. 34 of 100 March 30, 2015 Splash News 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. 35 of 100 February 4, 2015 Ramey Photo 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. 36 of 100 January 19, 2015 AKM-GSI Swift hit the NYC streets with her cat Olivia Benson wearing a Gestuz plaid wool coat over a teal top and Brandy Melville corduroy skirt, which she paired with bordeaux suede booties by Rag & Bone and a black top-handle bag. 37 of 100 January 17, 2015 Alessio Botticelli/Getty Images 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 ($290) for a Whole Foods run in N.Y.C. 38 of 100 December 26, 2014 Gardiner Anderson/Bauer-Griffin/GC Images 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. 39 of 100 December 24, 2014 NCP/Star Max/GC Images The star hit the Big Apple streets in a chic powder blue coat, floral embroidered tights, a sparkling headband, and a bold fuchsia lip. 40 of 100 December 22, 2014 NCP/Star Max/GC Images 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. 41 of 100 December 12, 2014 Gardiner Anderson/Bauer-Griffin/GC Images 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. 42 of 100 December 1, 2014 FameFlyNet Pictures Swift hit the streets of Londontown in a black lace Free People top, red plaid bottoms, patterned tights, and matching accessories. 43 of 100 November 23, 2014 Pacific Coast News 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. 44 of 100 November 15, 2014 Splash News Swfit ran errands in New York City wearing a rabbit-covered Talbots sweater, black skinny jeans, burgundy Rag & Bone booties, and her favorite Dolce & Gabbana top handle bag. 45 of 100 November 13, 2014 Alo Ceballos/GC Images The singer hit the streets in New York City wearing a festive navy sweater, burgundy skinny jeans, chic knee-high boots, and her favorite Aldo bag, all topped off with a green Topshop knitted beanie. 46 of 100 November 4, 2014 Jun Sato/Getty Images 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. 47 of 100 October 27, 2014 Raymond Hall/GC Images 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. 48 of 100 October 21, 2014 GVK/Bauer-Griffin/Getty Images 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. 49 of 100 October 12, 2014 AKM-GSI 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. 50 of 100 October 10, 2014 Beretta/Sims/Startraksphoto 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. 51 of 100 October 9, 2014 FameFlynetUK/FAMEFLYNET PICTURES 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. 52 of 100 October 8, 2014 Neil Mockford/Alex Huckle/GC Images 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. 53 of 100 October 7, 2014 Marc Piasecki/Getty Images 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. 54 of 100 October 6, 2014 Splash News 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. 55 of 100 October 3, 2014 Michael Stewart/Getty Images Swift stepped out in New York City in a flirty black Erin Fetherston frock and metallic Christian Louboutin heels. 56 of 100 September 16, 2014 GG/FAMEFLYNET PICTURES 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. 57 of 100 September 15, 2014 Raymond Hall/GC Images The songstress hit the Big Apple in a black Aritzia crop top and chic printed shorts that she accessorized with black booties and a forest green bag. 58 of 100 September 15, 2014 Raymond Hall/GC Images Swift made her way around New York City in a matching set by Aqua and hot pink Christian Louboutin peep-toe pumps. 59 of 100 September 14, 2014 Adam Nemser/Startraksphoto 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. 60 of 100 September 3, 2014 Beretta/Sims/Rex/REX USA 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. 61 of 100 August 13, 2014 Raymond Hall/GC Images 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. 62 of 100 August 12, 2014 Alo Ceballos/GC Images 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. 63 of 100 August 6, 2014 Raymond Hall/GC Images 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. 64 of 100 August 1, 2014 Splash News 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. 65 of 100 July 31, 2014 AKM-GSI 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. 66 of 100 July 30, 2014 Alo Ceballos/GC Images 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. 67 of 100 July 29, 2014 Sharpshooter Images / Splash 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. 68 of 100 July 24, 2014 Splash News 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. 69 of 100 July 22, 2014 FameFlynet 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. 70 of 100 July 18, 2014 Raymond Hall/GC Images 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. 71 of 100 July 16, 2014 Alo Ceballos/GC Images Swift stepped out in New York City wearing a belted navy tunic dress, leather Rag & Bone ankle boots, and a black Dolce & Gabbana bag. 72 of 100 July 14, 2014 Alo Ceballos/GC Images 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. 73 of 100 July 11, 2014 FameFlynet, Inc 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. 74 of 100 July 9, 2014 Raymond Hall/GC Images 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. 75 of 100 July 7, 2014 FAMEFLYNET PICTURES 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. 76 of 100 July 2, 2014 Alessio Botticelli/GC Images 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. 77 of 100 July 1, 2013 NCP/Star Max/GC Images 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. 78 of 100 June 30, 2014 INFphoto 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. 79 of 100 June 20, 2014 AKM-GSI 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. 80 of 100 June 19, 2014 FAMEFLYNET PICTURES Swift made a case for preppy summer attire in an A.L.C. blouse, bright short shorts, Oxford heels, and her trusty one of her favorite images" target="NEW">Dolce & Gabbana handbag. 81 of 100 June 18, 2014 Zelig Shaul/ACE/INFphoto.com 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. 82 of 100 June 17, 2014 Splash News 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. 83 of 100 June 14, 2014 GG/FAMEFLYNET PICTURES 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 peeptoe heels, and her signature bold red lip. 84 of 100 May 31, 2014 Jun Sato/GC Images 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. 85 of 100 May 4, 2014 FameFlynet Pictures 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. 86 of 100 May 2, 2014 AKM-GSI 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. 87 of 100 April 29, 2014 © DDNY/Broadimage 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. 88 of 100 April 28, 2014 © DDNY/Broadimage 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. 89 of 100 April 27, 2014 North Woods/Splash News 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. 90 of 100 April 26, 2014 PacificCoastNews Swift showed off her stems in a mini dress, layered under a moto style trench, and delicate ankle-strap sandals. 91 of 100 April 24, 2014 Kristin Callahan/ACE/INFphoto.com 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. 92 of 100 April 23, 2014 Splash News Swift countered a too-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. 93 of 100 April 22, 2014 Steffman-Turgoen/Splash News 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. 94 of 100 April 16, 2014 JDH Imagez/Splash News 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. 95 of 100 April 15, 2014 HUMBERTO CARRENO/startraksphoto.com 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. 96 of 100 April 14, 2014 JDH Imagez/Splash News 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. 97 of 100 April 12, 2014 Splash News/Incognito MP Swift embraced warmer weather in a a striped top, cuffed Hudson denim shorts, statement red shades, and her favorite shoe type: Oxford heels. 98 of 100 April 10, 2014 AKM-GSI 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. 99 of 100 April 3, 2014 PacificCoastNews Swift styled her checkered shirtdress for cooler weather with knitted tights and Oxford heels. 100 of 100 March 29, 2014 Christopher Peterson/Splash News 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. Was this page helpful? Thanks for your feedback! Tell us why! Other Submit