Chicago Streetwear Brands 2025

6 Streetwear Startups Putting Chicago Hip Hop in High Fashion [2025]

6 Streetwear Startups Putting Chicago Hip Hop in High Fashion [2025] - Tops and Bottoms USA

Welcome to the Style Side of the Chi

If you know Chicago, then you know we don’t follow trends—we set 'em. From corner ciphers to State Street boutiques, the Windy City’s got an energy that stays undefeated. Hip hop here isn’t just a genre; it’s a lifestyle, a language, a look.

And when it comes to style, Chicago streetwear doesn’t play. We’ve got brands that drip with cultural pride, hustle-born creativity, and just enough grit to keep things raw but refined.

From Godspeed’s rebellious vintage edge to Hyde Park Goods’ celeb-backed street styles, this new wave of Chicago labels is turning ambition into aesthetics — and giving the city a fresh face in global street fashion.

So, whether you’re stepping out of a Red Line car or pulling up to a pop-up in Bronzeville, these six labels are keeping our city's fashion pulse thumping loud—straight from the block to the Billboard charts.

Men's Latest Hip Hop Inspired Drip - Only At Tops & Bottoms ( Banner Ad)

Quick Drop Down:

  1. Godspeed
  2. Gunzinii
  3. Hyde Park Goods
  4. Roku Studio
  5. Roberto Vino
  6. RTA

Godspeed – Wear Your Ambition

Three male models wearing Godspeed graphic tees, styled in vintage streetwear. Photo by Tops & Bottoms.

Launch Date: November 2017

Style Vibe: Vintage rebel with a polished twist

Culture Footprint: Tied to East Coast rap royalty, loved by street collectors

Instagram: @godspeed

Available At: Godspeed Official, Tops & Bottoms, NWAHype, GOAT

Let’s talk mood. Godspeed is that brand you throw on when you’re feeling dangerous — in the best way. Graphic skulls, baroque angels, throwback fonts. It’s all designed to nod to hip hop’s raw energy while tapping into vintage Americana.

And don’t sleep on the LOX collab. Any brand tight enough to drop official gear for legendary rap groups is doing something right. It’s edgy, rare, and built for those who rock their gear like armor.

Gunzinii – New Voice of Urban Grit

Trio of male models in bold Gunzinii t-shirts, showcasing urban street style. Photo courtesy of Tops & Bottoms.

Launch Date: June 2023

Style Vibe: Grit-forward street staples, with strong visual storytelling

Culture Footprint: Lowkey heat — right now it’s underground, but bubbling

Instagram: @gunziniibrand

Available At: Civilized Clothing, Tops & Bottoms, Underground Clothing, The Shop 147

Gunzinii might not be a household name yet, but in Chicago’s boutique scene? They’re already making noise. Fresh N Fitted and Shop147 keep dropping Gunzinii collections that sell out fast, especially those bold “Strength Honor” and “Fearless” hoodies.

TikTok heads are clocking the brand’s varsity cuts and heavyweight fits, while early fans are calling it “next-up energy.” It’s raw, it’s graphic-heavy, and it definitely leans into that underdog spirit.

Hyde Park Goods – You Aren’t Invited

Three men standing side-by-side in Hyde Park Goods tees, repping Chicago streetwear. Shot by Tops & Bottoms.

Launch Date: December 2020

Style Vibe: Luxe meets loud, with heavy hip-hop DNA

Culture Footprint: Worn by rising rap royalty, built on Chi values

Instagram: @hydeparkgoods

Available At: Hyde Park Official, Tops & Bottoms, Capsule NYC

Started by Jacob Joseph — a South Sider now based in Houston — Hyde Park Goods is rooted in rebellion and realness. Think bold graphics, loud cuts, and a DIY spirit that screams “for us, by us.” What sets this brand apart is how many hip-hop names are co-signing it: Jeezy, GloRilla, Saucy Santana, DC Young Fly. It’s clear the music world’s listening — and watching.

This brand doesn’t just sell fashion; it builds narrative. It’s for the visionaries who know that looking good is only half the story.

Roku Studio – Drip from the Darkside

Models wearing Roku Studio t-shirts with graphic prints, blending anime and streetwear aesthetics. Captured by Tops & Bottoms.

Launch Date: December 2019

Style Vibe: Dark-graphic chic, Japanese art x skate style fusion

Culture Footprint: Cult streetwear following, sneakerhead-certified

Instagram: @rokustudiobrand

Available At: Tops & Bottoms, Era Clothing Store, D2ICHI, Urban Street Wear

Though technically born in NYC, Roku Studio has been fully embraced by Chicago’s streetwear tastemakers. Why? Because their pieces go hard — both visually and conceptually. With layered anime influences, “tear-drip” motifs, and fast-selling collections, Roku brings a moody, mystic energy to the streetwear game.

It’s not a brand for hypebeasts — it’s for those who treat fashion like art. You’ll catch DJs, skaters, and underground rappers in Roku, but blink and the drop’s gone. That’s the magic.

Roberto Vino – Fashion from Another Realm

Three male models in Roberto Vino tees, combining Italian luxe with Chicago street energy. Photo by Tops & Bottoms.

Launch Date: September 2021

Style Vibe: Italian luxury meets urban utility

Culture Footprint: Imported drip that’s getting real Chi love

Instagram: @robertovino_

Available At: Roberto Vino Official, Tops & Bottoms, The Shop 147, Underground Clothing

Yes, this one’s born in Italy — but Chicago has made Roberto Vino its own. The label’s sharp cuts, bold motifs (snakes, bullets, etc.), and soft cotton tees have found their way into city boutiques and streetwear lineups. It’s fashion-forward without being flashy, and perfect for pairing with crisp Air Force 1s or Italian-made kicks.

While it lacks local hip-hop roots, its Milan-meets-Midwest energy fits right in with the city’s global fashion aspirations.

RTA – Road to Awe

Group of men styled in RTA brand graphic tees, channeling dark glamour and elevated streetwear. Image by Tops & Bottoms.

Launch Date: October 2013

Style Vibe: Dark glamour, rockstar-meets-runway, French edge with street grit

Culture Footprint: MGK co-signs, high-fashion circles, spotted in Chi’s trend-forward boutiques

Instagram: @rtabrand

Available At: RTA Official, Tops & Bottoms, Feature.com

Born in L.A. with French luxury sensibilities, RtA (pronounced “ar-tee-ay”) isn’t a Chicago native — but you wouldn’t know it from how heavy it’s been hitting local boutiques. From distressed moto denim to hardware-drenched jackets, RtA is that brand you throw on when you’re not just trying to flex — but owning yourself fully. ,Feature.com

It’s the kind of label that’s been seen on everyone from Machine Gun Kelly to the Jenner sisters, but in Chicago, it’s often spotted on those who know their fashion history and aren’t afraid to mix luxury with street.

Final Fit Check

Chicago fashion is bigger than logos and labels — it’s a whole attitude. It’s South Side confidence, West Side flavor, and downtown polish. These seven brands represent all sides of the spectrum: from indie heat to global couture, from gritty rebellion to quiet flex.

So whether you’re rockin’ Jordans or Docs, clean lines or chaos fits, make sure your wardrobe speaks fluently in Chicago’s streetwear dialect. This city birthed style architects like Kanye and Virgil — and the new wave’s just gettin’ started. Now go get fresh. The Chi way.


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Streetwear FAQs

Everything you need to know to stay laced in Chi-Town’s dopest drip.

Q: What are the best streetwear stores in Chicago?
A: Jugrnaut, Leaders 1354, Saint Alfred, RSVP Gallery, and Tops & Bottoms are musts. Real heads know where to shop.

Q: What brands are trending in streetwear right now?
A: Godspeed, Essentials, Represent, Fear of God, Roku Studio, and Gunzinii are heating up fits from Chi to coast.

Q: What are the new streetwear brands to watch?
A: Gunzinii, Hyde Park Goods, Roku Studio, and Roberto Vino are making serious noise. All grit, no gimmicks.

Q: What kind of fits are popular in 2025?
A: Oversized tees, cargoes, layered textures, and loud accessories. It’s all about subtle statements.

Q: What’s different about hip hop tees vs. regular graphic tees?
A: Hip hop tees come with culture. It’s not just art — it’s attitude, message, and movement.

Q: Where can I buy streetwear in Chicago?
A: Tops & Bottoms, The Shop 147, Underground Clothing, and local gems like Iridium 77 and Black Rain got the goods.

Q: What sneakers go best with Chicago streetwear?
A: Classic Air Force 1s, Jordan 1s, Yeezy boots, and New Balance 550s — clean or cooked, just keep ’em loud.

Q: How do I style bold graphic tees?
A: Layer ’em with flannels, puffer vests, or open zip hoodies. Let the print lead the fit.

Q: Is streetwear just for men?
A: Nope — Chicago women are flexing just as hard, from cropped graphics to oversized sets and loud kicks.


Note: Tops and Bottoms is Chicago’s oldest streetwear store, and they sell their own products. No sponsors, no commissions—just honest style tips from someone who loves the game.

Copyright Disclaimer: Images in this blog are for informational purposes only. All rights belong to their respective owners. If you own an image and want it removed or credited, please contact us at estore@topsandbottomsusa.com


 Author's Twitter Account Follow Request and PictureRyan Shykh
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Streetwear lover, sneakerhead, and all about Chicago style. Sharing what I know to keep y’all looking fresh. 

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