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Winter Session Wants You to Embrace Your Baggage

A Colorado couple creates small-batch bags and accessories that serve a purpose and age gracefully



Portrait by Ashton Ray Hansen

Roy Katz and Tanya Fleisher want you to embrace your baggage. As founders of canvas and leather “carry goods” supplier Winter Session, the husband-and-wife team has put years of thought and hard work into their line of “refined utilitarian goods,” crafting a collection of versatile day bags, backpacks, totes and wallets that are built to last.

“We’ve approached this business from a design perspective, not a fashion perspective,” Fleisher says. “We’re building our products to be universal, timeless, functional, beautiful and personal. We don’t want you to think you need a new bag every season or every year.”

The business began as an inherent inclination to craft. Both Colorado natives, Fleisher and Katz come from a lineage of artists, designers and business owners. Fleisher grew up running around her grandfather’s darkroom and her father’s renowned Aspen clothing store, Pitkin County Dry Goods, and later studied art in Vermont and Chicago. Katz, a former architect, was born to a commercial-kitchen designer and a desktop publisher by day, seamstress by night. 


Winter Session bags in a variety of shapes and colors, from the jet-setting Weekender Bag (on sewing table, $389) to the classic Waxed Canvas Backpack, $289.  [Photo: Luca Venter]
We started out by saying, ‘let’s make things,’ and then through making things we realized that we really loved details.”— Tanya Fleisher

In the late 2000s, out of the tiny Chicago loft they lived in at the time, Katz and Fleisher started tinkering with wood projects on their landlord’s table saw and making shop aprons 
on a sewing machine a friend had found in a dumpster. 

“I had been working remotely as a production designer for my dad’s company,” Katz explains. “It was a lot of long days sitting in front of a computer. I was itching to work with my hands again.”

“We started out by saying, ‘let’s make things,’ and then through making things we realized that we really loved details,” adds Fleisher. “Details began to define what we were doing.”


A glimpse into the Denver workshop, where a Winter Session team member packs orders.  [Photo: Luca Venter]

We want you to use our products until they disintegrate.”— Roy Katz

The couple mimicked styles found on design and fashion blogs while they honed their craft. Aprons—which are still part of the Winter Session inventory—grew into upcycled bags, originally made from pieces of clothing found at thrift stores. The impetus came with the Garrison Bag, a heavy-duty carryall with handles, a shoulder strap and multiple pockets. 

“We were like, ‘Oh my gosh, I think we’ve created something that’s pretty much our own,’” recalls Fleisher. “We extracted details from that bag and incorporated them into other ‘sister and brother’ projects. All of our products are in the same family, but they have slightly different looks, functions and vibes.”

After finding success at craft fairs and wrangling their first wholesale account, the duo moved back to Colorado and set up shop in 2013, with the contents of their apartment, five sewing machines and a bunch of fabric in tow. Now working out of a shared 5,600-square-foot warehouse a few minutes east of RiNo, Katz, Fleisher and their team of five create a variety of “small-batch” wearables using CAD software programs, laser and die cutters, sewing machines, and good, old-fashioned hand-stitching. Their materials of choice are waxed canvas, leather sourced from Midwestern tanneries, and brass rivets and buckles—all picked for their durability and graceful patina. 


The stylish Waxed Canvas Roll Top Backpack in Grey + Natural Leather, $289. 

Driven by curiosity and a need to create, the team is also breaking into the home-goods sector. Canvas log-totes and hanging planters have been in the mix for a while, while desk accessories, leather fortune cookies and waxed-canvas throw pillows recently made their debut on the Winter Session website. 

“We just naturally want to make everything,” Fleisher says. Katz is quick to add: “And we want you to use our products until they disintegrate.”

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