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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In Character: Clark Griswold

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AHHH, summer vacation. It’s upon us. And if you don’t have any big holiday-weekend plans, maybe you want to cozy up on the couch and make like Rusty, sharing a six-pack with the ultimate road-trippin’ dad? Here, how to rip off his look. —erica

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A Barque polo that says, “My wife picked this out for me.”

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A Band of Outsiders khaki bomber—cool enough to attract the attention of the blonde in the Ferrari, maybe?

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YMC x Clarks loafers as classic as a trip to Wally World.

Another good Saturday activity: a deep dive into the “In Character” archives.

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Of a Kind

Can’t you see this Life After Denim polo hanging around a sixties block party, with a mai tai and a pack of Lucky Strikes? —erica

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In Character: Nolan Ross

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Of all of the questions that Revenge raises, the one that nags me the most is why none of the people desperately searching for Carrion have looked for it under Nolan Ross’s three collars. Seems like a decent hiding spot to me. When he’s not trying to protect Nolcorp from Grayson Global and The Initiative, everyone’s favorite tech wunderkind is showing Montauk what personal style is all about. Here, an outfit that transitions seamlessly from the board room to the Stowaway. —claire

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A red Orlebar Brown polo perfect for Victoria Grayson’s next Fire & Ice fête.

imageA Lucy Jay pocket square for wiping the sweat off his brow after narrowly dodging yet another CFO-turned-lover-turned-mole.

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A Brooklyn Tailors blazer with an interior pocket for discreetly transporting the shamu-cam.

For more “In Character” radness, head this way.

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Of a Kind

It’s pretty tough to get excited about a polo, but the spread collar on Kent Wang's—constructed from the same material the rest of the shirt is—makes it damn near perfect. Think Mike Brady mowing the lawn. —erica

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Of a Kind

I imagine that wearing this Pennsylvania-made Left Field polo, with its floral trim, would get you approached by women on the street. It’s like the fashion equivalent of having a puppy. —erica

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Of a Kind

Sweating: The two-tone chambray collar on this gray Apolis polo is just…GAH. It’s weird to buy the BF an Easter gift, huh? —erica

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