Fashion Selena Gomez Makes a Cutout Dress Look Classy Welcome to "Who Won Fashion Today," where we award the boldest, best dressed person of the day. Winning fashion doesn't necessarily mean you're wearing the most expensive, trendiest, or prettiest dress. Rather, we reward risk-takers—those that stay true to their personal style and make us go, "Now THAT is a LEWK." By Ruthie Friedlander Ruthie Friedlander Twitter Ruthie Friedlander is a New York-based writer, editor, and founder of the At Large Agency. She is also the co-founder of The Chain, a non-profit eating disorder support system for women in fashion and entertainment. InStyle's editorial guidelines Updated on February 9, 2017 @ 10:45AM Pin Share Tweet Email Photo: Robert Kamau/GC Images Hello world. Welcome to fashion month. Where there are going to be WAY too many winners of the day to feel fair giving just one person an award. Relax. Don't worry. We still will be telling you Who Won Fashion each day, but a warning to all contenders: competition is gonna be TOUGH. Selena Gomez's M.O. for Dressing Guys Is "Anything Gosling Would Wear" Yesterday, Selena Gomez (whom I typically prefer to see in a silk pajama set with heels over a frilly dress) was seen promoting 13 Reasons Why in a Proenza Schouler spring 2017 dress. The dress epitomizes the brand's spring collection, which played around with layering, moving silhouettes, and experimental shapes. The experiment worked, if you ask us. Selena Gomez's Standout Street Style Moments Palace Lee/INSTARimages.com Image zoom December 4, 2017 The singer put a chic twist on the bare trend. While out in London, Gomez wore a black sheer turtleneck (sans bra) with a patterned coat and orange-red heels for a pop of color. Palace Lee/INSTARimages.com Image zoom December 4, 2017 Before stepping out without a bra, Gomez wore not just one, but three other dresses, including this black one from Proenza Schouler. Neil Mockford/Getty Images Image zoom December 4, 2017 Gomez spent part of her day rocking a blue minidress with a Bardot cut and Trademark velvet slides. Neil Mockford/Getty Images Image zoom December 4, 2017 To kick off her über fashionable day, the singer wore bright red Mansur Gavriel with a floral print dress with an asymmetrical hem. SAV/Getty Images Image zoom October 22, 2017 The singer made a case for the pants-over-dress trend in a long, sleeveless gray sweater dress, black skinnies, and slingback pumps in N.Y.C. She paired the look with wet hair, round sunnies, and a black satchel. Christopher Peterson/Splash News Image zoom October 17, 2017 Leave it to Gomez to make sleepwear look chic. The singer was spotted in N.Y.C. while wearing a silk Olivia von Halle nightshirt ($490; neimanmarcus.com) as a dress, and she couldn't have looked better. She paired the look with simple sneakers and a gold necklace. Splash News Image zoom September 25, 2017 Gomez made her casual powder blue shirt and cuffed jeans look downright sexy by adding a pair of red Stuart Weitzman stilettos ($398; stuartweitzman.com). Her "Selena Grace" Coach bag ($395; coach.com), a sleek bun, and reflective round sunnies completed the look. Raymond Hall/GC Images Image zoom September 14, 2017 The singer was spotted out in N.Y.C. wearing the perfect outfit for the transitional weather. She paired an orange sweater, crimson miniskirt, and long gray plaid coat with bare legs and white accessories to create an ideal look for the end of summer. James Devaney/Getty Image zoom September 12, 2017 The singer took a break from the New York Fashion Week rush to grab dinner, and she kept things cool with her look. Gomez wore a sheer wine-colored dress (similar here) with red-tinted glasses and heeled black boots (similar here). Before grabbing a bite, the singer appeared at the Coach fashion show. North Woods / Splash News Image zoom September 10, 2017 Gomez stepped out for SoulCycle in N.Y.C. wearing a dark gray sports bra and high-waist leggings (shop a similar style here). She topped off the sexy workout look with Puma high-top sneakers, a herringbone coat, and reflective round sunglasses. The singer went with minimal makeup for the occasion, and slicked her short hair back into a low bun. Allan Bregg / SPLASH NEWS Image zoom September 4, 2017 Gomez made the most of the semi-official end of summer, wearing all white on Labor Day in a white graphic tee, Cotton Citizen joggers ($225; saksfifthavenue.com), and a pair of white sneakers. Team GT/GC Images Image zoom August 19, 2017 Gomez stepped out in L.A. wearing a flirty, feminine Khaite red midiskirt that's currently on sale for half off its original price of $780 ($390; matchesfashion.com). If it's sold out in your size, shop a similar style here. The star paired her statement skirt with a black long-sleeve shirt with a square neckline, a pair of square-toe white slides by The Row, and her very own Selena Grace Coach bag ($395; coach.com). PressPhotoBank / Splash News Image zoom July 11, 2017 The singer went for a stroll along the water in Malibu, Calif., while wearing a red off-the-shoulder Reformation dress ($198; reformation.com) that featured button detailing down the front and pockets on each of her hips. To polish off her low-key look, Gomez threw on a pair of thong flip-flops and accessorized with round wire sunglasses, pulling her short hair back into a low ponytail. PacificCoastNews Image zoom June 8, 2017 Gomez stepped out in L.A. in the perfect summery LBD, a Proenza Schouler crepe dress which featured spaghetti straps, a fitted bodice, and pleated skirt with metallic detailing. She paired the frock with a tight ponytail, smoky eye, peach-toned lip, and chunky black sandals (shop a similar pair here). The Mega Agency Image zoom June 8, 2017 The singer was white-hot in a Jacquemus top-and-pant combo. Her plunging shirt featured large armholes that cut all the way down to the top of her pants and showed off major sideboob. She paired the daring shirt with a pair of cropped gray pants, a statement belt, and a pair of white pumps (shop a similar pair here). The Mega Agency Image zoom June 6, 2016 The singer and The Weeknd stepped out for dinner after his Tuesday-night concert at the Barclay's Center in Brooklyn, N.Y. Gomez went braless in a curve-hugging black dress that turned see-through in front of the cameras. She paired the ensemble with strappy stilettos and a high ponytail. PressPhotoBankNY/MEGA Image zoom June 5, 2017 The "Bad Liar" singer looked chic in a Shaina Mote Eames black and white dress ($515; shainamote.com). She paired it with a leather jacket and matching heels. Rob Kim/Getty Image zoom June 5, 2017 Gomez stepped out in a hot pink bird-print onesie paired with metallic stilettos. She pulled her hair back in a ponytail and smoldered in smoky eye makeup. Robert Kamau/Getty Image zoom June 5, 2017 Being able to wear such a loud prints doesn't mean that Gomez won't pull off a classic look every once in awhile. The singer stunned in a navy and white side split dress with cat eye shades on Monday. Robert Kamau/Getty Image zoom June 5, 2017 Gomez showed off her toned legs in a structured cobalt blue dress affixed with a large oversized button. She paired the bold hued-frock with a pair of black sandals with a lucite heel. Robert Kamau/Getty Image zoom June 5, 2017 Gomez stepped out in New York, ditching a bra and donning a pop-of-color bright orange Christopher Kane dress instead. To complete the look, the chart topper left her jewelry behind and opted for a classic pair of classic black sandal heels. Robert Kamau/Getty Image zoom June 4, 2017 Gomez looked low-key in New York, pairing frayed-hem Re/done jeans with a black hoodie from her boyfriend The Weeknd's line of merch ($78; theweeknd.com) and black Stuart Weitzman booties ($575; nordstrom.com). She accessorized with a pink JW Anderson crossbody bag ($1,690; modaoperandi.com) and added a pair of yellow-tinted gradient shades. Robert Kamau/Getty Image zoom June 3, 2017 Gomez dined at Park Side Restaurant in Queens wearing a plunging light blue wrap dress with pink flowers. She accessorized with a pink JW Anderson crossbody bag ($1,690; modaoperandi.com) and peep-toe platform stilettos. Splash News Image zoom June 3, 2017 For a Saturday in N.Y.C., the young pop star wore a fuzzy sleeveless ALEXACHUNG sweater that featured multicolored stripes with a pair of high-waisted jeans cropped just above her ankle. She slipped on a pair of orange Mansur Gavriel sandals with a chunky heel ($475; net-a-porter.com), yellow-tinted sunglasses, and a small crossbody bag for an effortlessly cool look. JWNY Image zoom April 28th, 2017 Gomez stepped out for lunch in Beverly Hills on Friday in an edgy, denim-on-denim getup. After clapping back at critics of her new show 13 Reasons Why, the singer joined a friend for lunch on the patio outside the Montage hotel, and looked very cool in her high-waisted Re/Done jeans, vintage t-shirt, and oversized denim coat. Is she perhaps taking style cues from beau The Weeknd? For some reason we feel he would approve of this outfit, which Gomez topped off with—wait for it—a scrunchie. Prepare to see them in everyone's hair by next Saturday. TC / Splash News Image zoom March 31, 2017 Gomez headed to lunch in L.A. looking chic with sleek tresses, reminiscent of J.Lo's recent cut, and wearing a classic cool girl ensemble: dark wash J Brand skinnies that she cropped herself ($188; nordstrom.com), a plain white tee, round-lensed sunnies, and a pair of white crocodile slip-ons ($199; stuartweitzman.com). Vasquez-Max Lopes/AKM-GSI Image zoom March 28, 2017 Gomez looked effortlessly cool while strolling through Buenos Aires with her boyfriend, The Weeknd, in a black striped Isabel Marant dress ($1,350; available in beige at bergdorfgoodman.com), white Converse Jack Purcell sneakers ($65; nordstrom.com), and round sunglasses. For a similar strappy black patterned sundress, try this look via Topshop ($75). The Grosby Group/AKM-GSI Image zoom March 23, 2017 Gomez surprised high schoolers, with help from Coach and the charity Step Up, and discussed female empowerment with the young students. She looked casual and cool in a pair of dark wash, cropped jeans, a white tank, and a floral jacket (try a similar rose-print bomber here). Donato Sardella/Getty Image zoom March 14, 2017 Gomez was spotted leaving a pilates studio after a workout with some friends in a pair of black leggings from Alo Yoga ($82; nordstrom.com) and a baby blue crop top. Vasquez-Max Lopes/AKM-GSI Image zoom February 14, 2017 The singer was spotted out in New York City on Valentine's Day wearing a red hot dress and animal print sandals. She topped off her outfit with a cool black leather jacket. selenagomez/Instagram Image zoom February 9, 2017 Gomez braved the New York City snow in a chic winter white coat that featured a delicate bow accent at the waist. She paired the topper with a contrasting pair of black skinny pants and matching boots, and finished her ensemble with a white leather bag and red sunnies. Marc Piasecki/GC Images/Getty Image zoom February 8, 2017 The singer stunned in N.Y.C. in a mustard-colored ribbed Victoria Beckham dress with a red collar and cuffs. She paired the look with leopard-print sandals and loose, sexy waves. Mr. Exclusive/MEGA Image zoom February 8, 2017 Gomez radiated in a black and white cut-out Proenza Schouler dress paired with black sandals. Robert Kamau/GC Images Image zoom February 8, 2017 Gomez turned heads in the Big Apple in a flirty floral dress and too cool red bomber jacket that we can't get enough of. She completed her winning outfit with towering black heels and matching red sunnies. Splash News Image zoom February 07, 2017 The star was spotted at LAX Airport flaunting her toned midsection in a cropped black top and kick flare patchwork jeans. She topped off her look with a coordinating black coat, slingback heels, a neutral leather bag, and red sunglasses. Bauer-Griffin/GC Images Image zoom January 19, 2017 Gomez showed off her unique sense of style in Los Angeles when she donned a dinosaur-adorned Coach sweater ($695; spring.com) over a white turtleneck. High-waisted jeans, rose-hued sunglasses, and Kurt Geiger pumps ($230; kurtgeiger.us) balanced out her ensemble. JB Lacroix/GC Images Image zoom December 3, 2016 Gomez was spotted hitting the town in a chic black number made up of a wrap top with choker details, matching trousers, and strappy heeled sandals. A black leather bag and red manicure completed her Los Angeles-ready outfit. AKM-GSI Image zoom December 2, 2016 The "Same Old Love" singer stepped out on in a seriously chic pajama set: a navy and purple patterned silk set, featuring white trimming and buttons from Olivia Von Halle (oliviavonhalle.com; $423). She paired the set with a black duster coat and traditional black pumps from Casadei, wearing her dark brown hair in a low ponytail, and carrying a black wallet clutch. FameFlynet Pictures Image zoom November 28, 2016 To travel through LAX Airport, the actress opted for a cozy ivory sweater, skintight leather pants, and chunky black boots. Dark shades and a delicate necklace accessorized her classic look. starzfly/Bauer-Griffin/GC Images Image zoom August 9, 2016 While hanging out with friends in Australia, the star wowed in a black slipdress and coordinating coat that she draped over her shoulders. A pair of suede boots and bright orange nail polish topped off her number. Splash News Image zoom August 1, 2016 The singer touched down in Tokyo wearing a ribbed black crop top that showed off her super toned abs. She paired the piece with a matching cropped denim jacket, olive green Vetements drawstring sweatpants, and black Converse sneakers. Jun Sato/GC Images Image zoom July 13, 2016 The "Hands to Myself" singer channeled a '70s look in Los Angeles, styling her long hair and heavy bangs into a sleek 'do. Gomez flaunted her toned abs in a tiny gray crop top, which she paired with fitted black trousers, black loafers, and a glittery statement necklace. She finished off her retro-inspired ensemble with a denim jacket that she wore off her shoulders. Vasquez/Eagle Eye/Fameflynet Pictures Image zoom June 10, 2016 The 23-year-old donned an oversize Guns N' Roses graphic T-shirt and light blue bootcut jeans at LAX Airport, topping the look with black patent heeled boots, a black leather tote bag, gold aviator sunnies, a chic metallic watch, and rockstar bangs. Sharky/Polite Paparazzi/Splash News Image zoom June 3, 2016 Gomez hit the streets of New York City in an eye-catching red satin dress and metallic heels. Statement earrings and a coordinating cuff finished off her dazzling look. AKM-GSI, Inc. Image zoom April 10, 2016 The pop star sensation looked to Marques' Almeida for a tailored menswear take on classic denim. She breezed through airport security in Miami rocking an ab-baring bralette and slim-fit jeans styled with a matching frayed duster and simple sandals. Xposure/AKM-GSI Image zoom March 10, 2016 The star gave ruffles a sexy spin with this plunging red-hot Giambattista Valli number that she donned in Paris. She topped off the dramatic plunging frock with a sleek topknot. FameFlynet Image zoom March 9, 2016 Gomez attended a Louis Vuitton dinner party in Paris, where she opted for a sophisticated (yet sexy) strappy black Vionnet gown with a gauzy sheer overlay and Soebedar black mesh pumps. AKM-GSI Image zoom March 8, 2016 Selena arrived in Paris clad in a cozy pair of red Vetements sweats for the city's Fashion Week activities. She dressed up the comfy hooded logo-print sweatshirt and drawstring track pants with white heels. MPI99/Bauer-Griffin/GC Images 1 of 48 Advertisement Thanks again, Queen Kate (Young)! For putting Selena in this sexy sweet-meets-high fashion elegant black and white cutout asymmetrical dress.