Illustration by John Kenzie
Illustration: John Kenzie

1. Streetwear

Quote:From $165 for sneakers
The RealReal says:“Chicago is home to some of the biggest names in streetwear, so we’re leaning into sneakers and streetwear from brands like Nike, Yeezy, Balenciaga, and Off-White.”
Standout pick:Yeezy x Adidas Boost 350 V2

2. Handbags

Quote:From $525 for a clutch
The RealReal says:“Our Chicago shoppers gravitate toward the likes of Louis Vuitton, Gucci, and Hermès — classic pieces that fit into their everyday lifestyle.”
Standout pick:Louis Vuitton Pochette Accessoires and Neverfull

3. Watches

Quote:From $2,150 for a Rolex
The RealReal says:“Rolex is always a high-ticket brand on our site, but in Chicago, we see especially high demand.”
Standout pick:Rolex Submariner