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.”

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Rihanna
Credit: 247PAPS.TV / Splash News

Last night, Sienna Miller STUNNED in a Gucci gown at the Hollywood premiere of her new movie, Live by Night. But let’s be honest. We’ve seen a lot of gowns since Sunday. And while I’ll never tire of a pretty dress, looking at all these gorgeous women in heels and fancy dresses makes me yearn for a casual, cozy outfit.

Today, I really considered wearing sweatpants. But then I remembered I’m not Rihanna. Last night, Rih was hanging at Tao in New York City wearing a super cozy fleece lace-up jumpsuit from her eponymous Fenty x Puma Collection. And while she was wearing sky-high booties, that jumpsuit looked like the chicest snuggie we’ve ever seen. 3 Outfits to Wear with Rihanna's Fenty x Puma Trainer

With a Slip Dress and Tee
Credit: Courtesy

Image zoom With a Slip Dress and Tee

The slip dress is one of this season's hottest pieces—give it a dose of cool-girl appeal with a tee layered underneath, a statement-making purse, and a geometric cuff.

Shop the look: T by Alexander Wang tee, $85; net-a-porter.com. Babaton dress, $30 (originally $75); aritzia.com. Adorn Monde cuff, $52; adornmonde.com. Les Petit Joueurs purse, $640; shopbop.com. Fenty x Puma sneakers, $228; luisaviaroma.com. Courtesy

Image zoom With an Off-the-Shoulder Top and Joggers

Complement the sneakers with a pair of joggers, but then elevate it with a crisp off-the-shoulder top, a bejeweled choker, and a pretty velvet clutch.

Shop the look: Tibi top, $295; tibi.com. French Connection joggers, $50 (originally $138); frenchconnection.com. Fallon choker, $300; fallonjewelry.com. Mansur Gavriel clutch, $695; barneys.com. Fenty x Puma sneakers, $228; luisaviaroma.com. Courtesy

Image zoom With a Lace Cami, Bomber, and Culottes

Tap your edgy side with a bomber jacket (all the It girls are wearing them) and cool culottes, but blend it with hint of romance with a pretty lace cami and a delicate necklace.

Shop the look: Vrai & Oro necklace, $355; vraiandoro.com. Zara cami, $40; zara.com. Topshop bomber, $110; topshop.com. Mango culottes, $50; mango.com. Courreges duffel, $1,170; openingceremony.com. Fenty x Puma sneakers, $228; luisaviaroma.com. Courtesy 1 of 3 Advertisement