Winter Session (winter-session.com) founders Roy Katz and Tanya Fleisher may say their soft goods company started with a Craigslist sewing machine and upcycled material, but it probably began long before that. Fleisher’s father owns Pitkin County Dry Goods, the Aspen retailer celebrating its 49th year, so she grew up knowing about luxe, retail and longevity. “What I did take with me from all those years, crawling around under the clothing racks, helping out at the counter and later assisting on buying trips was an appreciation for quality—in materials, in design and in relationships,” says Fleisher. “All of those nice fabrics, interesting textures and wearable styles, I later learned, could be described as ‘high-end casual,’ and naturally, I was hooked.”
Their story is homegrown from Aspen High School in the late 1990s. The couple dated after performing in the school play, and kept in touch as they moved forward with their lives. After earning their degrees—he from the Southern California Institute of Architecture and she from the School of the Art Institute of Chicago—plus stints as far flung as Vermont, Los Angeles, Chicago, Italy and Mumbai they eventually reunited and formed Winter Session in 2010 while in Chicago.
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