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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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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Next Level: Long-ish Shorts

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Who wears short shorts? Not everyone. And if you’re looking to keep your upper thighs to yourself, here are four ways to do so. —erica

LEVEL I: Denim cut-offs—but in a totally unexpected way, thanks to Vladimir Karaleev

LEVEL II: These cotton Band of Outsiders suckers almost look like board shorts—and would be killer with a stacked sandal.

LEVEL III: Um, laser-cut polka-dots—that’s the 3.1 Phillip Lim way.

LEVEL IV: So loose and girly at once! How about these Steven Alan guys with a just-cropped top and a straw hat?

More “Next Level!” Come and get it.

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Of a Kind

I would happily stand up in a wedding where this Katie Ermilio for Steven Alan number was the bridesmaid dress. You know, in case anyone’s wondering. —erica

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Couple Up: January Jones and Ashton Kutcher

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What are these two most remembered for? The fact that he told her she should probably stick to modeling. Oof. But, they were so young! Just look and their toothy smiles, their fresh faces, and their outfits. —erica

January Jones: A fancy little Ben-Amun bobby pin, a jacquard Kenzo dress, and a thin Demylee cardigan.

Ashton Kutcher: A rumpled Save Khaki oxford, a tweed blazer from Steven Alan, and some Yuvi man jewelry.

More duos past their expiration date over here…

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Next Level: Mesh

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Brace yourself for the punniness ahead: These four pieces will have you looking like one hot mesh. —erica

LEVEL I: Just a sliver of see-through makes these Rebecca Minkoff loafers look a whole love more interesting.

LEVEL II: It’s like the strapless dress that you never have to hoist up, c/o Elizabeth and James.

LEVEL III: Thanks to this Steven Alan purse, you’ll know if you have your phone without even opening your bag.

LEVEL IV: Not only do the sleeves on this Jonathan Simkhai jumpsuit look fly, but they also allow for some serious air circulation. 

All the “Next Level” you can eat handle!

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Of a Kind

Never had a hankering for a sleeveless trench (or, really, knew such a thing EXISTED) until spying this Steven Alan one. —erica

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Couple Up: Ryan and Rachel

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Are Ryan Gosling and Rachel McAdams getting back together?! THE INTERNET WANTS TO KNOW. But, in the meantime, here’s your chance to get a little R&R, via the couple’s most iconic look. (Yes, our survey says that the red carpet/pink hair scene at the SAG Awards in 2007 is even more memorable than this). —erica

Ryan Gosling: The perfect black tie from Rag & Bone, a Steven Alan tux jacket, and not-to-shiny patent lace-ups from Mr. Hare.

Rachel McAdams: A sparkly silver Edie Parker clutch, a halter trapeze dress by Ali Ro, and slick white Sophia Webster pumps.

Like what you see? More twosomes here…

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Next Level: Dressy Jumpsuits

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Is there a reason—a good one—that a jumpsuit can’t get a little serious, a tad grown-up? Don’t think so. These are four that mean it. —erica

LEVEL I: Steven Alan goes super-classic. You know, for a jumpsuit.

LEVEL II: Huh! This A.L.C. getup looks like separates without the trouble of putting an outfit together.

LEVEL III: Yah, yah, strapless. But put a blazer over this 10 Crosby guy—a tuxedo jacket, even?—and it’s ready for action.

LEVEL IV: Get a load of those pinstripes and pleats, via Band of Outsiders. This sucker is very Serious Business Lady in a Melanie Griffith way.

Fall down the “Next Level” rabbit hole.

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Of a Kind

Kangaroo pockets: not just for hoodies anymore. Right on, Steven Alan. —erica

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