In Character: Randy Taylor

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Roster of nineties Tiger Beat heartthrobs: Joey Lawrence, Luke Perry, Devon Sawa, and little, chubby-cheeked Jonathan Taylor Thomas, who, on Home Improvement, played the middle son of a man who grunted to express emotion. Still got a soft spot for JTT? Well, then, you can hang this in your locker cubicle. —erica

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A sleeveless plaid shirt—from Thom Browne—worn like a jacket for reasons still unknown.

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Frame overalls that Brad probably made fun of.

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Diemme boots ready to hang on the set of Tool Time with Al.

Get your television fix over here.

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Couple Up: January Jones and Ashton Kutcher

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What are these two most remembered for? The fact that he told her she should probably stick to modeling. Oof. But, they were so young! Just look and their toothy smiles, their fresh faces, and their outfits. —erica

January Jones: A fancy little Ben-Amun bobby pin, a jacquard Kenzo dress, and a thin Demylee cardigan.

Ashton Kutcher: A rumpled Save Khaki oxford, a tweed blazer from Steven Alan, and some Yuvi man jewelry.

More duos past their expiration date over here…

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Of a Kind

Short-sleeve button-downs are inherently dorky. And this Barque one embraces that. —erica

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Of a Kind

This is a surf club jacket. That’s how M.Nii is selling it, anyway, and I’m buying. —erica

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Couple Up: Johnny Depp and Kate Moss

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If it was possible for us to do a reader poll in this space, we’d have to ask who you <3 <3 <3 more, Johnny and Kate or Johnny and Winona? Tough decisions, these. A look at the former pairing’s style, while you ponder. —erica

Johnny Depp: A yellow-and-black knit cap from Eugenia Kim, a no-nonsense leather jacket by Scotch & Soda, and an Apolis gingham shirt.

Kate Moss: Simple-but-cool Lauren Wolf studs, a pretty major LBD from Motel, and a wide belt c/o Alice + Olivia.

For more couples we miss, click here.

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Couple Up: Katy Perry and Russell Brand

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To fully understand the drama of these two, you’ve gots to see the teary-eyed, show-must-go-on scene in the movie Katy Perry: Part of Me. Watch it! No, you really should. Really, really. For real. —erica

Katy Perry: An armor ring from Eddie Borgo, a gunmetal sequin dress by Milly, and cheeky-as-they-come Charlotte Olympia pumps.

Russell Brand: A nearly sheer Hartford shirt, a white Neil Barrett blazer, and a three-finger ring from Erica Anenberg.

For more couples that once were, head here.

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Couple Up: Paul Rudd and Jennifer Aniston

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Paul Rudd and Jennifer Aniston have been a couple in two movies, The Object of My Affection and Wanderlust. But, turns they did stint together in real life, too, waaay back in 1998—and I’m pretty into the idea of them as a twosome. Maybe they broke up because of the soul patch he had for part of their relationship? —erica

Paul Rudd: A Pierrepont Hicks tie, a brown Everlane shirt, and a corduroy jacket from Billy Reid.

Jennifer Aniston: A Carven shrug (yes, shrug), a strapless column dress from Cedric Charlier, and a sparkly necklace by Tom Binns.

Get all the “Couple Up” you can handle if you head this way.

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Couple Up: Adam Brody and Rachel Bilson

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Adam Brody is a married man now, but long before he shacked up with Leighton Meester, he dated her near-twin, Rachel Bilson. IRL and on the teevee! Here’s what their Seventeen-worthy relationship looked like. —erica

Adam Brody: Super sunglasses fit for a music festival, a red-and-black tee from Saturdays, and navy Supergas.

Rachel Bilson: Rolled-up Denim Refinery jean shorts, a sleeveless Americana shirt from Chaser, and a leather-cord necklace by Vanessa Mooney.

More couples of yesteryear right over here.

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Couple Up: Emilio Estevez and Demi Moore

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Ok, tell me: Doesn’t throwback Demi Moore look like she could front a band playing Knitting Factory in Williamsburg? ANYWAY, get a load of the Brat Pack couple—they were engaged in the eighties, even. —erica

Emilio Estevez: Common Projects loafers, a perfect white T-shirt from Billy Reid, and Incotex gray pants.

Demi Moore: Slouchy pants from Otte, an Everlane cardigan, and Warby Parker glasses.

Double down on your “Couple Up” over here.

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Of a Kind

A Reigning Champ down vest printed to look all sweatshirt-y—smart. —erica

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