Of a Kind

Anyone want to teach me to pull-off a wide-leg trouser? Because these M. Patmos ones are where it’s AT. —erica

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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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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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Of a Kind

No, no—drop-crotch chinos are not easy to pull off. But doesn’t NLST make you want to try? —erica

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Couple Up: Carson Daly and Tara Reid

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Does anything take you back to the year 2000 faster than hearing the names Tara Reid and Carson Daly? Basically as iconic (and now, in retrospect, as hilarious) as Y2K. Here’s what all that looked like. —erica

Carson Daly: A silver Miansai ring or five, an almost-brown Brooklyn Tailors blazer, and a crisp Seize sur Vingt shirt.

Tara Reid: Glittery pumps from B Brian Atwood, suspendered Brunello Cucinelli pants, and a black Iro bandeau.

More couples who are no more here.

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Of a Kind

Just chillin’ in some baggy, half-sheer Nomia pants. You know. —erica

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Of a Kind

Something says you’d wear the crap out of these Crazy Wind pants (which, by the by, aren’t so crazy at all). —erica

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Of a Kind

Few things impress me more (ok, style-wise, guys) than a girl who can work a wide-leg trouser. Yah, Osei-Duro. —erica

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Weather Vain: Amagansett, New York - 68 and Clear

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Love ya, Montauk, but for a really chilled-out, do-nothing day, Amagansett is where it’s at. This is what to wear for a day that’s a bit too cool for an ocean dip. —erica

Clockwise from top left: 

+ A couldn’t-be-breezier Ace & Jig top that’s ready to catch some music at The Stephen Talkhouse

+ This Lila Rice ring on your finger and a coconut-coconut cupcake from Mary’s Marvelous in your hand—dreamy.

+ Because Otaat / Myers Collective knows you don’t need a big bag to stroll Main Street. 

+ A beach cardigan—yah, that’s what L’Agence calls it, and we’re down.

+ Sandals that look good AND could handle some gardening—leave it to the Steven Alan x Dr. Scholl’s collab.

+ Some laid-back Current/Elliott pants—because the toughest decision you should have to make today is whether you want the Clam Bar staple fried, steamed, or raw.

Head to “Weather Vain” heaven.

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