Couple Up: Miley Cyrus and Nick Jonas

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How psyched was Disney about these two holding hands, do you think? But when they broke up—well, Miley says that’s what sparked her teenage rebellion (which led straight into her early 20s rebellion, obvs). Get into their adolescent power couple look below—and here, too. —erica

Miley Cyrus: A beaded Shashi bracelet, a striped tee from NSF, and washed-out Siwy cut-offs.

Nick Jonas: A blue Brooklyn Tailors suit, a Stock Manufacturing Co. oxford, and a tie by John Varvatos.

Get all the “Couple Up” you can handle.

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A patterned chambray Kiriko tie? LOVE. I’m sure you’re shocked. —erica

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Couple Up: Mandy Moore and Zach Braff

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When these two broke up, Mandy Moore wrote, oh, most of an album, Wild Horses, about him. Sample lyrics: “And I know you loved me in your way / I’m looking forward to looking back on these days.” Well, here’s to looking back, then? —erica

Mandy Moore: Tom Ford aviators, a cozy-looking Tess Giberson sweater, and a Rebecca Minkoff bag.

Zach Braff: Worn-in jeans from Ron Herman, a short-sleeve, just-dorky Steven Alan shirt, and a York St. by J. Press belt with a big, fat buckle.

Double down on your “Couple Up.” Right here.

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Lately, I’ve been really feeling the idea of a blue suit—not navy or royal, exactly, but something between. Basically exactly what Shades of Grey is doing here. —erica

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Move over, blue suede shoes. There’s a blue suede *jacket* (from Todd Snyder!) in town. —erica

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I’m kind of all about the fabric of this Alex Mill shirt. You dig? —erica

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Couple Up: Owen Wilson and Kate Hudson

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If these two were a high-school couple, they would be pictured in the yearbook under the header “Best Beach Hair” (and, ok, probably “Best Smiles” too, those jerks). Here’s a tribute to those Owen-plus-Kate days of yesteryear… —erica

Owen Wilson: Super-dark Acne jeans, a navy Everlane polo, and a long-sleeve tee from James Perse.

Kate Hudson: Ripped Current/Elliott jeans, a Rachel Zoe vest (worn as a top), and a lariat necklace by Vanessa Mooney.

More match-ups right this way.

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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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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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