Seven Questions: Winter Session

I’ve known Winter Session co-founders Roy Katz and Tanya Fleisher for a few years now; we all buddied up back in Chicago, before making our respective exoduses (them to their home-state of Colorado, me to my home-state of NY). Over that time, I’ve watched their brand evolve from a small side project, to one of the best carry goods labels in operation today – and I’m not just calling them that because they’re friends. The amount of care, thought and craftsmanship that goes into every piece they make is palpable. Holding a Winter Session bag or wallet in your hands, you can tell it’s coming from two people who love what they do, and who are damned good at it too.

Roy and Tanya recently took some time out to discuss finding their niche, their ambitious new collection, and making the jump from hobby to career. Here’s what they had to say.

Well Spent: Give us the Winter Session origin story.
Winter Session: We started Winter Session in 2010 while living in Chicago. It started out as a side project with a friend of ours – with no real intention to start a company, just a desire to start working with our hands again. (At the time, Roy was logging too many hours on the computer doing freelance architectural drawings, and Tanya was just finishing her MFA). We were living in a converted storefront flooded with sunlight, much like our present shop and studio in Denver, and the space was naturally conducive to working on projects.

Since it was an independent, creative pursuit, we spent a lot of time messing around, exploring materials, and making mistakes. At that point our use of leather was minimal. When a Chicago-based company asked us to design and produce a set of leather accessories for all 60 of their sales reps, we had a lot of learning to do. That’s when we went knocking on Horween Leather’s door, and our ideas for what Winter Session could become really started to take shape.

Over the last couple of years, a number of new carry goods brands have popped up. What sets Winter Session apart?
You’re right, there’s been an explosion of new brands recently – especially in leather goods. We try not to get too distracted by what other people are doing though, and just focus on making our products the best they can be.

We’re about quality and simplicity, so you won’t find any bells and whistles on what we make. Our products aren’t loud; they’re not cute or fancy. They’re quiet, dependable, and sturdy. They’re both functional and elegant. We’ve spent a lot of time working to fuse great design, top quality materials, and unisex appeal into a product that’s actually affordable. We strive to address the tiniest details without overdesigning. Finding a balance between all of these things is not easy, but that’s where we feel the strength in our brand lies.

When Winter Session first launched, the two of you made everything yourselves. Is that still the case?
It’s true that since our very first run of floppy totes and work aprons in 2010, we’ve logged a great many hours on the sewing machine, at the cutting table, and on the stitching pony. But we’ve never done it all completely alone. Our apartment in Chicago doubled as our workshop, and for the first year we had a lot of help from friends and a few interns from the School of the Art Institute of Chicago. For a short time we also outsourced some of our larger volume orders to local Chicago sewing contractors. But since our move to Denver, we’ve brought everything back under one roof. We’ve hired two full time and two part time employees to help with everything from social marketing and outreach to machine sewing to packing boxes. The two of us still spend quite a bit of time at the sewing machine, but we now have a great team working right beside us.

You recently added a slew of new products to your collection. Can you tell us about those? Which – if any – are your favorites?
This is the first time we’ve felt we actually have a ‘collection’. We started with the Garrison Bag in the fall of 2011 and since then have had all sorts of ideas for companion pieces (our sketchbooks are full of them). But between fulfilling orders for Garrison Bags and working on custom/collaborative projects, we’ve only just recently been able to bring some of these ideas into fruition.

We’re particularly excited about the Day Pack and the Day Bag, as they help to provide for a variety of daily carry needs, for different sorts of adventures – while maintaining a classic, minimal aesthetic. Especially now that we’re based in Colorado, where hiking and commuter biking are strong, mainstream activities, the zip-top Day Bag and the streamlined Day Pack are natural additions to the family. These pieces were also designed with longer journeys in mind: we’ve received positive feedback on the new bags from friends and customers who are frequent airplane travelers.

You guys do a lot of collaborations. How do you choose which brands to work with? Any upcoming collabs you can tell us about?
Collaborating with other brands and individuals both challenges and inspires us. It allows us to explore our materials in new ways and gives us an opportunity to learn new techniques and get to know new audiences. We choose our collaborations based on projects that intrigue us, people we want to work with, and what we have time for (if it weren’t for the time element, we’d probably take on a lot more!).

We’ve had a blast collaborating with DRIFT Eyewear in Chicago, and the leather eyeglasses case we designed together has become one of our personal favorite pieces. We’ve always been fans of paper goods, so when Chad Doane of Doane Paper in Kansas City asked us to work with him on a line of leather and canvas goods to accompany his products, we didn’t hesitate (you’ll see several additions to the WS+DP collection in 2014).

In the coming months we’re excited to work on some new projects with Juniper Ridge and Scout Regalia. Closer to home, we’re developing a special bag with Journeyman & Co., a new Denver-based company that works closely with designers and makers to curate themed, custom collections, each benefiting a related cause.

Your workshop also doubles as a storefront. What made you decide to open it to the public?
While sewing bags and pounding rivets in the front of our Chicago apartment, we would often spot people peeking through the front windows, trying to see what was going on. People love to see how things are made. When we were looking for spaces to move into in Denver, we only considered storefront locations because it would give us an opportunity to engage immediately with our new community. If we were to settle into a warehouse space somewhere, we might be operating for years without anyone knowing we were there.

Our workspace and shop – the Winter Session Outpost – is directly accessible from the street and acts simultaneously as a workshop, showroom, retail venue, and event space. People who come in can check out our finished products while also watching our production process firsthand. Because what we do is a little bit unusual, especially for our neighborhood in Denver, seeing that process gives a first-time visitor a direct and tangible understanding of our work. Kids especially get a kick out of seeing the workshop in action, and even our FedEx and UPS delivery guys have started to take an interest.

What would you say to someone who’s still on the fence about buying from Winter Session.
Well, first we’d say: sorry, man – must be uncomfortable sitting on that fence! We’re not going to try to convince you that our products are the best. We’ll leave that up to you to decide. But we can tell you that we have a lot of return customers who keep coming back to us.

As much as we love the opportunity to sell directly to our customers via our web shop, we also strongly value our presence in brick and mortar shops around the US and abroad, because it gives people an opportunity to experience our products in person. Winter Session wares are created with intention and care, and we’re glad that for many people, this is mirrored in the purchase – our products are not an impulse buy.

We encourage you to find a stockist near you (or visit us in Denver, of course!) where you can experience the depth of the leather’s color, the texture of the waxed canvas and the weight and feel of the piece for yourself. Whether you’re investing in a sizeable bag or a small wallet or accessory, Winter Session will be a companion for a long time to come, and we want it to be the right fit.

For price and purchase info, visit Winter Session.