Couple Up: Andre Agassi and Brooke Shields

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Andre and Brooke were a total curveball—ok, that’s the wrong sport, but you know what I mean. People is better at this than I am: When the two divorced in 1999, the mag titled its story “Double Fault.” Ah, there it is. Here, a look back. —erica

Andre Agassi: Silver hoops from Simon Sebbag, a T by Alexander Wang windbreaker, and a sweat-proof Huf hat.

Brooke Shields: Way-classic Super sunglasses, a polished Blk Dnm blazer, and coordinating silver hoops by Alexis Bittar.

More couples who once were!

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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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Couple Up: Anne Heche and Ellen DeGeneres

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Ok, LOOK at these two with their matching sunglasses. Is now the right time to say “I can’t even?” I hope so. —erica

Anne Heche: A wavy A Link necklace, a knit Gentryportofino dress, and a pair of AJ Morgan shades.

Ellen DeGeneres: A black silk shirt from Acne, a super-classic white Rag & Bone blazer, and (coordinating) Elizabeth and James sunglasses.

More cute (former) couples thisaway.

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Of a Kind

Blue Summer Linen Blazer by 7115 for Of a Kind

BUY / 65 of a kind / $160

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Couple Up: Jack Nicholson and Anjelica Huston

On-again, off-again for nearly all of the seventies and eighties—so much dramz with these two. And so much good style. Can we get a primetime cable-TV movie about them? Please? —erica

Jack Nicholson: A Rag & Bone knit tie, a cotton-and-linen Billy Reid blazer, and Raen sunglasses.

Anjelica Huston: An easy-breezy Cook & Gates tote, a button-front Shaina Mote dress, and a simple K/LLER necklace.

Get into the “Couple Up” zone over here.

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Of a Kind

Summer Linen Blazer by 7115 for Of a Kind

BUY / 35 of a kind / $160

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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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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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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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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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