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UNFORTUNATELY, CLOSED! Wayward is the place for the city dweller and outdoor enthusiast to find durable and stylish gear to support their daily confrontations with the environment. Whether it’s the city streets or the rolling hills, Wayward is stocking heritage brands as well as newcomers that are up to the task of the many interests of the modern gentleman.


BY: Christopher Blatner Contributing writer

Chicago is tougher than you think. Yeah, Chicagoans have a rep for being friendly and all. They’ll say hello to you on the street, and even look you in the eye while doing it. Ask someone for directions … directions you’ll get, good ones, probably accompanied with a smile and a firm handshake. But don’t mistake that politeness for frailty. It takes fortitude to inhabit this city. With its network of nearly 6,000 miles of roads, alleyways, elevated train tracks, and bike trails; you’re going to need those directions you were so courteously provided. You’re also going to need some tough-as-hell gear for exploring that vast urbanscape; equipment that can tolerate the elements, withstand a commute, help you navigate and capture every moment of the journey.

Enter Wayward Collective. Mixed in among the secondhand shops, record stores, and eateries along Milwaukee Avenue in Wicker Park, this shop has the goods to meet the needs of the urban dweller with a passion for both style and function. You’ll find wares that easily plow through a day of moving about the city and do double duty to serve the same urbanite that puts on the leathers to ride up the eastern coast of the lake to explore the sand dunes of Indiana and the serene beach towns of Michigan. Wayward was founded on the principles of exploration and supplying the seekers and wanderers as they create and encounter the city and beyond.

Wayward is a place for the dreamers, seekers, and globetrotters to converge … a place to find the essentials that will not only support the journey but also enhance the experience.

Entering the shop you are welcomed into a modern space with classically rugged touches like black scraped-wood floors and timber-paneled walls, perfectly balancing the urban-outdoor vibe that Wayward embodies.  Moving through the store you’ll encounter apparel, bags, accessories, and lifestyle goods from brands you recognize and many under-the-radar suppliers specially curated by Wayward. Everything you require is here. Whether it’s a backyard get together or a trail hike in your plans, you’ll find growlers, candles, flashlights, utility tools, bandanas, traveling cocktail kits, and more.

Looking for something extra unique? Be sure to check out the tightly chosen collection of vintage wear available from some of the most iconic heritage brands. On our most recent visit, we encountered a killer blue and white Triumph moto jacket, emblazoned with the Union Jack logo. You never know what you’ll find.

Any adventure needs to be documented and Wayward has that covered with a selection of instant cameras from Lomography, Polaroid, and Leica. You’ll also find journals from Field Notes and Mollyjogger to chronicle all of your profound reflections about the world as you encounter it.

Wayward is a place for the dreamers, seekers, and globetrotters to converge … a place to find the essentials that will not only support the journey but also enhance the experience.


Need some new old tunes? Reckless Records is a few doors down. It’s been in the neighborhood since ’88 and has one of the best collections in the country

Feeling the urge for a taco? You’re in between arguably two of the best taco shops in the city: Antique Taco and Big Star

CYTIES pick-up: A badass grey t-shirt collab between Wayward and local tattoo shop Great Lakes Tattoo

Searching for a new bag? Go no further. You won’t find a better selection in the city