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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Of a Kind

Have you eyeballed Lauren Manoogian's sweaters yet? Because they’re the sorts of things you’d probably wear for the next three decades. —erica

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In Character: Lane Kim

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I know that Gilmore Girls is a TV show and that we didn’t actually get to watch Lane Kim grow up, but it feels like we did, right? There was the purple-hair-dye incident! The drunken phone call to her mom! The twins! And all the while, she managed to be Rory’s bestie—hardly an easy task. —erica

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A collared, short-sleeve Crippen shirt that Mrs. Kim would approve of.

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Studious-looking Selima glasses that still worked with her Hep Alien, rocker-girl look.

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An elephant sweater from Giada Forte, as comforting as breakfast dates with Rory at Luke’s.

For a whole lot more “In Character,” click!

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Of a Kind

Knits to the beach?! Kordal makes all that look so viable. —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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Couple Up: Claire Danes and Ben Lee

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Did you listen to Ben Lee’s music for the first time because he was Claire Danes’s BF? Didya? We get it. They were just so…so…late-nineties, minimalist, living-in-Soho cool. —erica

Claire Danes: Open-back Alexander Wang sandals, a sleeveless turtleneck sweater from Yigal Azrouel, and perfect stovepipe khaki pants by Jason Wu.

Ben Lee: Black Acne pants, a loud, floral Vito Rhody shirt, and beaten-up Golden Goose sneakers

More nostalgic pairings to be had!

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In Character: Billy Madison

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Graduation season is upon us. And if this was 1995, we’d all be patting Billy Madison on the back for passing 12th grade (well, all the grades, really). Below, how to cop his back-to-school look. And if this isn’t enough for you, check out this tribute from Four Pins—it’s for real. —erica

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A Marweather hat that rules. Just like O’Doyle.

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A preppy-as-they-come Band of Outsiders sweater—with the sleeves ripped off, for better golf-carting.

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A baseball jersey, from Opening Ceremony, that the hot third-grade teachers gotta respect.

Whoa, so many more “In Characters.” Have at ‘em.

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Weather Vain: Providence, Rhode Island - 68 With a Chance of Rain

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Hey, now—don’t let the rain in R.I. get you down. Here’s how to keep things cheery (check out that bright white) in the Creative Capital. —erica

+ Native rain shoes that don’t actually look like rain shoes.

+ A VeraMeat necklace—simple but super-considered (not unlike the coolest hotel in town, The Dean?).

+ Rag & Bone white jeans, ready for a late-afternoon oyster-mushroom po’ boy at The Grange.

+ A sweater from Everly, in case you get chilly sitting in one of the 1492 seats at the Columbus Theater.

+ One of those linen tees, from 81 Hours, that you’d wear more than you wish to admit.

+ Mociun earrings that the kids at RISD would die over.

+ A Will Leather Goods wallet with a wristlet strap, to keep your hands free to clutch a White Electric Coffee mocha…and bagel.

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Next Level: Palm Prints

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Here in NYC, we don’t have palm trees in our yards, but we can have them on our bodies (or in our smaller-than-they-should-be apartments). Leaf it to these four to deliver a dose of the tropics. —erica

LEVEL I: A Katie Kime tray—for your jewelry or for all of the change you’re saving to plan a getaway.

LEVEL II: Who says there’s gotta be green? Not Kenzo.

LEVEL III: Band of Outsiders takes the ultra-cozy approach: a potted palm sweater that looks really ready to curl up with a paperback.

LEVEL IV: MSGM isn’t afraid of an out-there color combo, and you shouldn’t be either.

Get a whooooole lot more “Next Level”

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In Character: Olive Oyl

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Ok, get this: Did you know that Olive Oyl has been around longer than Popeye? She made her first appearance in 1919, and he didn’t come into being for another decade—and which point, he did his best to steal the spotlight. Well, here’s to you, Olive, and those ginormous feet of yours. —erica

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A red-and-white J.W. Anderson sweater that’s as wholesome as a can of spinach.

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A Victoria Beckham skirt with a hit of yellow that would really catch Bluto’s eye.

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Flat N.D.C. boots—because who wants to carry around Swee’Pea in heels?

Get all of the “In Character” you can handle, here and now.

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