It's not easy to identify what exactly avant-garde is; as fashion evolves and changes, brands (and the collections they put out season after season) need to consistently evolve and experiment in order to stay at the cutting edge. Such is the same for retail, especially if your stock and trade is exposing both newcomers and longtime fans to some of the most forward-thinking labels in the fashion industry today. Such is the challenge for Gallery Aesthete and its founder and owner Stephen Naparstek.

With a small shop nestled in the city of Chicago, Gallery Aesthete, in its own words, proposes a sense of identity, meaning, and purpose to a niche community within the creative world. In real terms, the shop is an attempt to expose shoppers to the craft—and ultimately, permanence—of visionary fashion design. While its neo-brutalist retail location and curated brand list may have average fashion fans feeling slightly intimidated at first glance, Naparstek's aim is hardly pretentious; the way this type of creativity thrives is not through stuffy pretension, but in the open dialogue and appreciation of design.

In an effort to showcase his unique storefront, explain his own creative process and share some of his favorite designers with the wider fashion community, Naparstek has partnered with Grailed to offer incredible garments from both Gallery Aesthete and his personal archive. Ranging from well-known designers like Rick Owens, Julius and Boris Bidjan Saberi, to lesser-known names like Guidi, Lost & Found by Ria Dunn and Forme 3’3204322896 (aka Forme D'Expression), this project aims to not just expose shoppers to some boundary-breaking fashion, but also show how these designers and stores like Gallery Aesthete are enriching the global fashion conversation in their own ways.

Enjoy our exclusive Q&A with Stephen, and scope the items listed below.

Lead image courtesy of Bob Coscarelli.

All other photography courtesy of Matthew Reeves.