In Character: Van Wilder

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Ok, no, this is not a GOOD movie—and not just because Tara Reid is the most serious thing going here. But if you’re looking for a rainy-day excuse to spend a few hours with your couch and Ryan Reynolds? Well, it’s as good as anything going. Also: College-boy dressing in 2002—something to behold. —erica

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A Zanerobe shirt that eventually gets him lei’d.

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An Alexander McQueen chain wallet that makes the frat brothers of DIK especially nervous.

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A Saturdays hat, worn backwards to convince Taj to go for Naomi (“That’s ‘I moan’ backwards.”). 

More, more, more “In Character!”

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Couple Up: Madonna and Sean Penn

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Oof, were these two trouble. Their nickname was S&M, for chrissake, and during their time married in the mid-eighties, his rap sheet was possibly as long as his list of IMDB credits. I mean, they look like they’re up to no good, right? Course that was also their appeal. —erica

Madonna: A blacker-than-black Wendy Nichol bag, a lace-up shirt c/o The Kooples, and striped shorts from Thakoon Addition. 

Sean Penn: A slim Todd Snyder polo, a leather jacket by Nudie Jeans, and charcoal Rag & Bone pants.

Dip into the “Couple Up” archives.

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Of a Kind

Cacti don’t need a lot of water, but these Katin trunks? They’re looking for a whole pool of the stuff. —erica

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Couple Up: Lenny Kravitz and Lisa Bonet

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These two never met a pattern they didn’t like. I mean, to get inside their closets…oh, wait: That’s exactly what it’s like to be Zoe Kravitz, that beautiful creature. Damn her. —erica

Lenny Kravitz: A loud Yarnz scarf, a leather jacket from Billy Reid, and striped pants by Neil Barrett.

Lisa Bonet: A colorful Growing Jewelry necklace, a floral patchwork shirt from Markus Lupfer, and Saturdays sunglasses.

For more old favorites, head this way.

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Couple Up: Jared Leto and Cameron Diaz

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Wait, these two were really together for four years? How does that not seem possible to me? Tell me! Someone! So much time—and so many haircuts (some of them matching, even!). —erica

Jared Leto: A Cheap Monday ring, Baldwin camo pants, and a flowy white Apiece Apart shirt.

Cameron Diaz: A big Clare Vivier bag, slim J Brand black pants, and shades from Elizabeth and James.

Whoa, there’s a whole lot more “Couple Up” action to be had.

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Couple Up: Andre Agassi and Brooke Shields

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Andre and Brooke were a total curveball—ok, that’s the wrong sport, but you know what I mean. People is better at this than I am: When the two divorced in 1999, the mag titled its story “Double Fault.” Ah, there it is. Here, a look back. —erica

Andre Agassi: Silver hoops from Simon Sebbag, a T by Alexander Wang windbreaker, and a sweat-proof Huf hat.

Brooke Shields: Way-classic Super sunglasses, a polished Blk Dnm blazer, and coordinating silver hoops by Alexis Bittar.

More couples who once were!

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In Character: Shawn Hunter

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Ok, gang: The Boy Meets World spinoff premieres in July. Are you ready? Do you know how to find the Disney Channel on your teevee? While you figure all that out, let’s revisit the original and Shawn’s just-bad-boy, TGIF-approp look. —erica

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A Scotch & Soda leather jacket that really sells the rebellious-best-friend thing.

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A Kris Van Assche necklace Mr. Feeny probably thinks is silly.

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A Shipley & Halmos flannel that, along with that hair, draws in all the girls at John Adams High.

This way to the “In Character” archives…

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Of a Kind

A Hitsman tie worthy of a superhero, if you ask me. —erica

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Of a Kind

Super-washed-out Hawaiian print? Smooth move, M.Nii. —erica

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Couple Up: Tom Green and Drew Barrymore

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These two were supposed to get married on Saturday Night Live—mmmhmm, really. Apparently, Drew got cold feet, married Tom anyway in July 2001, and then filed for divorce 163 days later. It was all very confusing, even for those of us not intimately involved. —erica

Tom Green: A classic Neil Barrett bow tie, a Brooklyn Tailors tux, and Duncan Quinn lace-ups.

Drew Barrymore: A shiny Lauren Merkin clutch, a green-and-blue Anna Sui kimono, and teardrop earrings from Alexis Bittar.

If you’re looking for more duos you nearly forgot existed, we have a whole bunch.

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