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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Of a Kind

Short-sleeve button-downs are inherently dorky. And this Barque one embraces that. —erica

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In Character: Mrs. Euphengenia Doubtfire

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Mrs. Doubtfire is a hilarious and wonderful movie—and not just when you watch it (over and over on VHS) as a 10 year old. Here, how to follow Kim K.’s lead and mimic the namesake character’s look. —erica

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A shirt, by MSGM, that might catch fire when she leans over the stove.

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A Sophie Hulme bag that is decidedly grown-up and dependable—just like this dad in drag.

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Suno's loud floral blazer, worn with a matching dress, that looks even kookier next to Pierce Brosnan in his swim trunks.

It’s “In Character” madness over here!

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Couple Up: Johnny Depp and Kate Moss

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If it was possible for us to do a reader poll in this space, we’d have to ask who you <3 <3 <3 more, Johnny and Kate or Johnny and Winona? Tough decisions, these. A look at the former pairing’s style, while you ponder. —erica

Johnny Depp: A yellow-and-black knit cap from Eugenia Kim, a no-nonsense leather jacket by Scotch & Soda, and an Apolis gingham shirt.

Kate Moss: Simple-but-cool Lauren Wolf studs, a pretty major LBD from Motel, and a wide belt c/o Alice + Olivia.

For more couples we miss, click here.

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Next Level: Shocking Pink

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Think pink! No, like, REALLY pink. Here are four ways to do bubblegum with a bang. —erica

LEVEL I: Oooh, so polished with a pair of jeans, Amanda Uprichard!

LEVEL II: Antiqued brass keeps the bright-as-they-come stones in these Dannijo studs from looking too Barbie. 

LEVEL III: What do you call this Jenni Kayne dress besides perfect, really?

LEVEL IV: 3.1 Phillip Lim delivers the most serious, double-breasted cut in the most fun-lovin’, look-at-me hue.

Want four more? Have at it.

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Weather Vain: Chicago, Illinois - 44 With a Chance of Rain

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+ An Each x Other trench as white as the tablecloths at Pearl Tavern.

+ Ah, these Dieppa Restrepo loafers! The color of some GT Fish & Oyster king crab legs.

+ The perfect, easy-fitting black silk pants c/o Raquel Allegra.

+ A Carven shirt just crisp and business-y enough for the West Loop.

+ What do you know: a two-finger ring, from K/LLER, that’s actually a breeze to wear.

+ A Jenni Kayne blazer in Cubs colors—cause it’s officially that time of year, guys.

+ Shoulder bags—not great for layers. A backpack like this Jerome Dreyfuss one—a whole lot better.

+ This Orly Genger by Jaclyn Mayer bracelet = just weird enough for the out-there cocktails from Aviary

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Track Star: Alynda Lee Segarra of Hurray for the Riff Raff

The Vibe: Small Town Heroes, the newest album from the folk band Hurray for the Riff Raff, is filled with a whole lot of feminist rage and resignation from the singer Alynda Lee Segarra. She sounds pained and complex, but her look is a little more straightforward: think fifties housewife with a bone to pick.

The One-Song Intro: “I Know it’s Wrong (But That’s Alright)”

The Look, Recreated: This sleeveless denim shirt from Cheap Monday, this retro dress by Rachel Antonoff, and this floral pencil skirt by Derek Lam. maitri mehta

It’s music madness if you click this way.

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Couple Up: Katy Perry and Russell Brand

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To fully understand the drama of these two, you’ve gots to see the teary-eyed, show-must-go-on scene in the movie Katy Perry: Part of Me. Watch it! No, you really should. Really, really. For real. —erica

Katy Perry: An armor ring from Eddie Borgo, a gunmetal sequin dress by Milly, and cheeky-as-they-come Charlotte Olympia pumps.

Russell Brand: A nearly sheer Hartford shirt, a white Neil Barrett blazer, and a three-finger ring from Erica Anenberg.

For more couples that once were, head here.

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Next Level: Fringe

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How to wear fringe without feeling like you’re repurposing a razzle-dazzle-y  Halloween costume? Four ideas—good ones, if you ask me. —erica

LEVEL I: Well! It doesn’t get more ladylike than this Adam Lippes dress.

LEVEL II: Hey, Coachella, these Loeffler Randall sandals are looking for you.

LEVEL III: Tibi makes backless feel a smidge more approachable.

LEVEL IV: This jacket = very Devil Wears Prada-on-an-acid-trip, c/o MSGM.

If you’re looking for more “Next Level,” go ahead and click here.

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Of a Kind

I’m pretty sure I had this Rachel Comey top in third grade. But that does NOT mean I wouldn’t buy it again. —erica

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