Chicago:

Harajuku’s Best Vintage Shop for Casual Streetwear and Denim Finds

6-3-15 2F, Jingumae, Shibuya, Tokyo 150-0001

April 10, 2025

Japan is home to some of the best fashion and shopping in the world, and vintage fashion plays a huge role in that. Entire neighborhoods like Shimokitazawa and Kichijoji are packed with second hand shops, making it easy to get overwhelmed by the sheer number of options. And let’s be honest—not every place is worth the dig. Vintage shopping in Japan often requires time, patience, and a lot of effort to sift through the racks—but finding that one piece that makes it all worth it.

Over the years, we’ve gone from broke college students hunting for deals to adults looking for more curated, long-lasting pieces. One store that’s consistently delivered on both ends of that spectrum is Chicago.

While you can find Chicago locations across Tokyo, the two in Harajuku remain our top picks. The main Harajuku branch carries everything from vintage Carhartt pants, graphic tees, and sweatshirts (you might even spot your alma mater) to a solid mix of outerwear and accessories. They also stock vintage Levi’s, though in our experience, we’ve had better luck with denim at the Takeshita-dori location. 

Easy Vintage Shopping in the Heart of Harajuku

What sets Chicago apart is the balance between quality, variety, and price. It’s not the cheapest secondhand shop out there, but prices are fair for what you’re getting—especially when compared to trendier curated stores that often have a higher markup.

While Harajuku isn’t typically the first stop for secondhand shopping in Tokyo, Chicago is a reliable go-to if you want to mix vintage browsing into your Harajuku day. Plus, both shops are located on busy, easy-to-navigate streets, making them a low-effort, high-reward detour.

Whether you’re looking for a vintage souvenir, a standout streetwear piece, or just love flipping through racks, Chicago is one of those shops that never lets us down.