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“Tattered and torn but not distressed,” is how the 22-year-old Chicago-born musician Vic Mensa describes his personal style. These adjectives and this qualification could also apply to YEEZY Season 1, Kanye West’s debut collection for Adidas Originals, which the designer posits as a brave new paradigm for clothes—the fashion equivalent of the iPhone. But more than just glossy technology, the YEEZY collection channels savage grace and complex character—outsider qualities shared by four young musicians chosen for this portfolio by West himself.

Three of them call the Windy City their birthplace and home, a fact evident in a sound that’s emotionally exposed and a voice that’s socially aware. “For some reason when I’m in Chicago,” Tink says, “my music feels more like my original sound—unfiltered and raw.” The 20-year-old, whose 2015 hit “Million” references the late icon Aaliyah, describes herself as an old soul, mature beyond her years, who as a kid watched The Jeffersons and Soul Train with her father. “You grow up quick coming out of Chicago,” she says. “You go to school and you see friends and over the summer they pass—just reckless violence. You become numb to it and it gives you a tough skin.” Her upcoming album, Think Tink, will delve into the intense subject matter that’s made her one to watch since the 2012 song “Bonnie and Clyde.” “I feel like I’m the voice for my generation, especially for women,” she says. “My album is a day in the life of a normal human being, and that’s why I know it’s going to connect because I’m not dancing around the truth.”

What’s in the water in Chicago? As Mensa explains, the city lacks both the vain glamour of L.A. and the relentless pace of New York, which gives its artists a chance to reflect on a life more ordinary. “It’s not Hollywood,” he says. “You don’t grow up seeing movie stars hopping out of limos. We draw from different influences. It’s cold and gray outside right now, which doesn’t make me want to write a song about palm trees and beautiful women. I feel more compelled to talk about what these bricks made me feel.” Though Mensa’s 2015 breakout single “U Mad” features West and a kind of braggadocio not new to hip-hop, he holds himself responsible for sketching a picture of reality. “So many people are content with believing the bullshit they’re told,” he says. “My mom raised me to question authority. I’ve never been good with it. The idea of respecting something because that’s the way it is never resonated with me. I don’t know how to bow down.”

Fetty Wap, meanwhile, doesn’t know how to be anything but himself. There aren’t deep parables in his songs. They’re simply portraits of a 25-year-old from Paterson, New Jersey. “I just want people to know me, to know who Fetty Wap is,” he says. “I’m not trying to send a message—just my sound, my vision, my art.” Not to mention his hooks, which made “Trap Queen” a massive top 10 hit that lifted Fetty Wap to fame and mad acclaim. “I love doing them,” he says. “They’re the best part of a song.”

Newly signed to West’s G.O.O.D. Music, 32-year-old Chicagoan Holt makes no play for easy access with his music, eschewing genres for a sound that fuses hip-hop and rock. “I was signed previously as a rapper but I don’t rap at all anymore,” he says. “This music I’m producing has no genre yet. I’m sure people are going to put it into one, but I won’t. I just make sounds.” A forthcoming song, “Perfect,” off Holt’s next album, encapsulates his tendency to shun labels. “Those people who say you can’t do something,” he says, “they’re very much wrong and they deserve to be called out for it. This song is calling them out. It’s like, all I ever wanted to be was perfect, so I tried. That’s the lyric. It’s got super gangster beats on the chorus but live drums on the verse, then breakdowns and a lot of guitar. It’s everything in one.” The freeform approach is most true to his city—a historical center of blues, jazz, soul, house, and rock. And much like the YEEZY collection, it emphasizes individual expression over any preconceived notion of style, format, or taste.

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