Couple Up: Jared Leto and Cameron Diaz

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Wait, these two were really together for four years? How does that not seem possible to me? Tell me! Someone! So much time—and so many haircuts (some of them matching, even!). —erica

Jared Leto: A Cheap Monday ring, Baldwin camo pants, and a flowy white Apiece Apart shirt.

Cameron Diaz: A big Clare Vivier bag, slim J Brand black pants, and shades from Elizabeth and James.

Whoa, there’s a whole lot more “Couple Up” action to be had.

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Track Star: SZA

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The Vibe: The 23-year old rapper from St. Louis started making music just a few years ago, and, hey, she’s already been signed to Top Dawg Entertainment. She’s like a female Miguel, with a hypnotizing voice and dark beats, and her style has a coolest-girl-at-recess mood.

The One-Song Intro: “Babylon”

The Look, Recreated: This jersey tee from T by Alexander Wang, a pair of leather gym shorts by Capulet, and some classic Cheap Monday canvas high-tops. —maitri mehta

 More music! If you click right here!

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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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Track Star: Grimes

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The Vibe: Claire Boucher’s music and style are pretty ineffable, but she  calls the former “ADD music” and the latter “anime-goth.” Ok, then. You do you, Grimes.

The One-Song Intro: “Genesis”

The Look, Recreated: These silver flatform brogues from Jeffrey Campbell, this pattern-mixing Suno jacket, and this abstract leopard slip dress by Cheap Monday. maitri mehta

Get your “Track Star” fix here!

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Of a Kind

This Cheap Monday dress is all about a NYE that’s more about the eating than the partying. —erica

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Of a Kind

Yes, yes—fashion sweatshirts are such a thing, but with its sheer sleeves, this Cheap Monday one feels legit dressed-up. —erica

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Track Star: Savages

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The Vibe: Their sound is tough, punky, and severe—and so is their look, with all kinds of of masculine jackets, buttoned-up tops, and cropped haircuts.

The One-Song Intro: “Shut Up”

The Look, Recreated: A sharp gingham blouse by Equipment, a menswear blazer from A.L.C., Cheap Monday black skinnies, and a gold locket by Soixante Neuf. —julie alvin

Get lots more music-y goodness here.

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Of a Kind

Didn’t know I needed a blood-red denim jacket until I spied this Cheap Monday number. —erica

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Weather Vain: Pittsburgh, Pennsylvania - 73 and Partly Cloudy

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Ah, it’s the kind of weather you set your thermostat to. Here’s how to get that most out of a lovely day in the ‘Burgh. —erica

Clockwise from top left:

+ Cuffed white denim shorts from Paige—laid-back enough for a long stroll through Pittsburgh Public Market.

+ The sort of Boy. by Band of Outsiders shirt that says, “I’m about ready to break out my back-to-school look.”

+ A Steven Shein bracelet as sleek as the dining room at Habitat.

+ A so-cool Fleabags clutch that’s ready to take any day—especially one as prime as this one.

+ Cheap Monday sneaks that can hold their own at PNC Park.

+ This Orly Genger by Jaclyn Mayer necklace—totally ready to spend some solid time at the Andy Warhol Museum.

Way more where this came from! Get all the “Weather Vain” action here.

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In Character: Krusty the Clown

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How do you make an angry, substance-abusing clown seem at least 7% more kid-friendly? Bright, crazy clothes. Here’s how Krusty (or, if you’d rather, Herschel Shmoikel Pinchas Yerucham Krustofsky) half-heartedly sells his persona. —erica

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A YMC shirt just business-like enough to keep Sideshow Bob Mel in line. 

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A blue bowtie, made by Forage, not the Krusty Korporation.

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Cheap Monday pants—as green as the hundred dollar bills he uses to light his cigarettes.

Get all the “In Character” action you can handle here.

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