Jaden Smith and New Girlfriend Odessa Adlon Make Casual Look Cool

Don’t expect Jaden Smith to show up in board shorts and a Hawaiian shirt when it’s time to hit the beach. On a trip to Miami with actress Odessa Adlon, his rumored new girlfriend, the always-original actor put a unique spin on warm-weather style by revisiting the look of the ’90s: a kitschy pair of patchwork MSFTSrep jeans and a black T-shirt covered in eagles and lightning bolts. Throw in a set of freshly bleached dreads and plenty of PDA with Adlon, and you have Smith at his casual best.

Adlon’s own offbeat fashion choices make her an equal standout ahead of her small-screen arc on Nashville. Here, she followed Smith’s lead by doubling down on retro essentials with a Simpsons tee, choker, and belted mom jeans—a combo pulled straight out of 1995. To that, Adlon added hoop earrings, ankle boots, and a single red rose that looked like a romantic gift.

The couple’s low-key look underscores one of fashion’s great ironies—that no one loves ’90s nostalgia more than those who didn’t really live through it. Having spent years in skorts and lace chokers, Gen Xers may never want to see those trends again, while current teens can’t stop embracing the era’s hallmarks. Smith’s love of the decade is particularly well documented—he frequently cites Spike, the bleach-blond sometimes villain from Buffy the Vampire Slayer, as one of his style icons—and it seems like he has finally found someone who shares his enthusiasm. Young, in love, and fashionably in sync—we expect plenty more throwbacks ahead.

Ashley Olsen Gives Geek-Chic Dressing a Cool Twist

Ashley Olsen has always known the game-changing power of a good pair of shoes, and yesterday in New York, she proved the importance of dressing from the ground up yet again. The designer typically favors a muted palette where the rest of her look is concerned, and her elegant olive coat was just the right way to counterbalance lo-fi sneakers.

To give her optic-white kicks an unexpected geeky twist, Olsen accessorized them with marled pink socks. She also pulled out a more familiar styling trick, namely carrying two bags at once. Retro shades and an oatmeal funnel-neck top were the only other additions she made to her voluminous statement topper.