Photos by Nathan Michael.

I first learned about Winter Session from the founders of local apparel consulting group Single Needle. We were having coffee together, when one of them, noticing my Filson bag, told me I should give the brand a look, as their stuff was similar. To be honest, I was a little skeptical. Up until that point, I hadn’t come across any truly impressive Chicago makers. That Winter Session was not only making here, but also supposedly producing goods on par with Filson’s, well it was a little hard to believe.

But then I checked out the Winter Session site. The bags certainly had the look down – clean, classic, functional. And the environmentally responsible materials listed on the about page also piqued my interest. So, when I found out that WS was going to be at that month’s Dose Pop-Up Market, I made a point of stopping by. And I’ve been a fan ever since. The bags really are great; super well-made, and excellent looking. And the co.’s founders, married couple Tanya Fleisher and Roy Katz, are two of the nicest people I’ve met in Chicago.

Tanya and Roy were kind enough to invite myself and photographer Nathan Michael into their absolutely stunning workshop / apartment, and answer a few questions. Here’s what they had to say.

Well Spent: Are you from Chicago?

Winter Session: No. We both grew up in Colorado in small mountain towns. We’ve gotten a healthy dose of city life, though, after living and working for several years in Los Angeles, Mumbai, and now Chicago. We moved here so that Tanya could attend the MFA program (in Fiber and Material Studies) at the School of the Art Institute. We’ve been here for three years now.

What neighborhood do you live in?

When we first came to Chicago to look for apartments, we happened to stay with some friends in Andersonville. We ended up finding a great live / work space closeby, a few blocks from the lake. For the most part we have everything we need within walking distance.

What’s the best part about owning a business in Chicago?

The best part about starting a business here is the wonderful people we have met through the work that we do. We feel really lucky to have tapped into such a supportive community of folks throughout the city who are doing all sorts of interesting things – artists, designers, retailers, writers, etc. It’s a network that continues to grow in organic and unexpected ways and it makes our work worthwhile.

What’s the worst?

So far nothing comes to mind. It’s our first time running our own business, so we don’t have much to compare it to.

Your thoughts on Chicago style…

Hmmm… that’s a tough one. The style in this city is highly variable, changing with the weather and the neighborhood. Each time we venture into other parts of the city, we come away with a new opinion about the style here. Broadly, Chicago style seems to be a bit more conservative and practical than that of the coastal cities. People tend to dress for personal comfort rather than public show. That said, you still get to see quite a bit of experimentation in personal style, especially in warmer weather. Maybe a good way to describe it is that Chicagoans tend to take themselves less seriously than in places like New York or L.A., so they have a little more room to play.

I’m visiting the city for the first time, and I’ve only got 24 hours. What should I do / where should I go?

Not sure if anyone could ever fit all of this into 24 hours, but here’s a shortlist: Sunrise at Oak Street beach, breakfast at Floriole Bakery, Chicago Architecture Foundation Boat Tour on the river (getting to see the city from this perspective is a must), browse beautifully curated objects at Morlen Sinoway Atelier and then at Post 27, venture to the Northside for a light lunch and killer coffee at Ch’ava Cafe in Ravenswood, head to Andersonville to check out locally-made furniture and objects at Haymaker Shop, pick up a bottle of wine at In Fine Spirits and have dinner at Great Lake (awesome salads and probably one of the best Neopolitan style pizzas you’ll ever eat), or, heading south again, at Ruxbin. Either way, ending up at Longman & Eagle in time to sample some top-notch whiskies and savor a late-night pretzel with Welsh rarebit at the bar before spending the night upstairs in one of their 6 custom-designed rooms.

What’s at the top of your holiday wishlist?

Navy Camp Boots from Oak Street Bootmakers. Grey William Wool Vest from Imogene and Willie. Sunglasses from Persol. Sage Garrison Bag and Navy Billie Roll-up from Winter Session. Wagon #3 from WELCOME Los Angeles. Tripod Table/Stool from Strand Design. Turned wood Totem by Morlen Sinoway.

To view the complete Winter Session photo set, check out Nathan Michael’s Tumblr.