The Most Stylish Chicago Rappers Right Now

Image via Complex Original

The understated gangster.

Neighborhood: The Low End

Moonie's got that neighborhood dopeboy rich look that many try to emulate. He keeps it very neat and clean with just enough edge to stand apart from others. Many rappers overdo it with big chains, but Moonie always rocks jewelry and outfit combos that don't overshadow his sense of style.

The streetwear hippie.

Neighborhood: West Side

Purp has the whole streetwear hippie thing thing on lock. From the hair to the accessories, he takes many risks and it ends up working well for him. The Save Money affiliate is definitely the stand out member when it comes to style.

Where hip-hop, streetwear, and punk collide.

Neighborhood: Wild 100's

When it comes to being stylish, Holt is on a planet by himself. He's probably the biggest risk-taker on the list. He mixes a clean punk rock look with a dark streetwear aesthetic like nobody else. Catch him rocking fresh Vans, Japanese-exclusive jerseys, and a black-on-black Just Don cap.

Always on that new shit, never trying too hard.

Neighborhood: South Side

Rockie has always been fresh when it comes to fashion, but since signing with MMG he's been killing things. From Bape and Balencaga, to Hood By Air and Pyrex, he's doing it right. He has a very "don't care what I got on" attitude about his style that makes everything flow well.

Chicago's most stylish crew.

Neighborhood: West Side

When it comes to vintage 'Lo, the most premium of denims, and rare footwear, nobody does it better than Project Mayhem. Coming from the West Side, these five MCs hold it down correctly in the Chi—not an easy feat. They consistently rock fresh 'fits as a group without looking like a hip-hop boy band. Props for that.

A style maverick.

Neighborhood: Matteson

Back when the Cool Kids were jamming, their ode to the early 90's look was undeniable. From fat gold chains with classic NBA jerseys to acid wash jeans. Mikey definitely helped bring that retro style back, and he's never looked like any other rapper out with amix of high-end designer, retro fashion mash-up that's all his.

Bringing raw Chicago style to the masses.

Neighborhood: Englewood

Based on his style and influence alone, Keef is easily top five. He made the already infamous "dreads and Trues" look bigger than Chicago, and many have followed his every fashion move since he came out—for better or worse. Undersized polos with the collar popped, the Moncler vest that he made pop, True Religion Jeans with gravity-defying sag, and tons of Gucci—he's helped define the particular style of his hometown. 

Chicago's trendsetter.

Neighborhood: Dixmoor (Harvey World)

Mano's style has been in a constant evolition over the past few years. He's always the first to get on something, then the first to hop off it when it becomes over-saturated. He does a great job of blending luxe brands with true streetwear, and for that reason he's been a game changer for style in Chicago.

Classic and understated streetwear aficionado.

Neighborhood: Wild 100's

There's nothing bad to say about Mikkey's style—a lot of the top players in Chicago rap agree. He keeps things simple, with a splash a trend every now and then. Mikkey is a true coniseur of timeless rap style. Everything looks great on him—but he's at his best keeping it simple with a crisp tee, gold chains, a varsity jacket, and a new  pair of Jordans.

The best-dressed rapper in the world.

Neighborhood: South Side

He's a worldwide trendsetter and arguably the best dressed/most stylish rapper of all time. Coming from the southside of Chicago, 'Ye has always had the fashion game on lock, and kids all over the world been following his footsteps. From the pink polo days to the leather sweatpants wave, it's crazy to see how much his style has changed over the years (and how much style has changed because of him). Usually, as rappers get older they lose touch with what's hot and wind up looking corny, trying to replicate what the "the cool kids are doing." Kanye is the father (no pun intended-congrats Ye!) of what the cool kids are doing. Kanye is Fashion.

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