Round Two
Clothing store · Wicker Park ·

Round Two

Clothing store · Wicker Park ·

Buy, sell, trade vintage tees, sweatshirts, sneakers

friendly staff
great prices
curated vintage
good vibe
good selection
cool shop
fun vibes
limited-edition drops
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null
Round Two by null

Information

1501 N Milwaukee Ave, Chicago, IL 60622 Get directions

Credit card accepted
Debit card accepted
Wheelchair accessible entrance

Information

Static Map

1501 N Milwaukee Ave, Chicago, IL 60622 Get directions

+1 646 866 9408
roundtwostore.com
@roundtwobyroundtwo

Features

•Credit card accepted
•Debit card accepted
•Wheelchair accessible entrance

Last updated

Dec 22, 2025

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Three House to bring fun vibes to West Town | Eater Chicago

"Owned by Chris Russow, Round Two is a Wicker Park clothing boutique with a rabid fanbase — customers wait in lines for limited-edition drops — and those connections are expected to help draw attention (and celebrities) to Three House." - Ashok Selvam

https://chicago.eater.com/2021/1/20/22240937/three-house-west-town-round-two-half-evil-counter-chicago-avenue-bar-biscay-wishbone
Round Two

M. A. K.

Google
Visiting Chicago for a week from LA (actual LA—shout out mid city!). Shopping at Round Two today punctuated an already amazing trip. Dom and Brandon were phenomenal; savvy professionals deeply connected to the culture. The selection was outstanding. We found sneaker heat in our sizes (4.5W and 12M) that felt impossible to obtain elsewhere. We also stumbled across some absolutely dope vintage that we copped as well as a few newer streetwear pieces. We could have spent several hours rifling through all the gear. HIGHLY RECOMMEND. We will be back! 🙏🏽🙌🏽💪🏽

Michelle M.

Google
very cool 2 level shop for well curated vintage tees and sweatshirts - price point is great and lots to look at. loved the vibe and atmosphere and had fun looking through all the sports themed tees. wish i had found the right piece but alas - i’ll check back next time i’m in town!

jack A.

Google
Pulled up sold a bunch of pairs. Smoothest buying experience in the city. Sold 51 Pairs and got cashed out in minutes. if you are looking to sell only go to ROUND TWO & ask for DOM!

Mario N.

Google
So grateful for their five dollar item sale on the roof a few months back during the summer! I got some wonderful vintage sweaters that I love dearly.

Madvillan

Google
Very nice employees. When I went in to sell some Kobe 6s they offered me a fair price. Even though I wasn’t going to take it, I recognize that the business needs to make money and I left with the knowledge that Round Two was a great sneaker store that will always greet customers with kindness and respectable offers.

Eduardo V.

Google
Sell a lot of my vintage clothing here. Dom, Chris, and Juan always give the best payouts and fair and honestly great prices for pieces. My go to spot to buy and sell

Jassmin B.

Google
As a RVA native, I love Round Two!!!! Big Thank you to Rhyu and Dom for the love ✨

Chris S.

Google
I’ve been coming here since they opened. Dom, Chris, Brando, every one else have shown me nothing but love. As someone who wears a size 13 sneaker, it’s often difficult to find good sneakers at a good price and Round Two provides both. It’s my favorite sneaker store in the city and I’ll always show love.