6 Chicago fashion-tech startups & their fall fashion tips

by Emerson Dameron
September 26, 2014

Chicago may lack the fashion-world cachet of Los Angeles, Paris, New York, or Milan, but its colder months make it an interesting case study in clothes. The dropping mercury imposes rigorous demands on our wardrobes. Fortunately, we have a good number of fashion-tech startups to help us survive the autumn and beyond.

The Patternbase is a local textile-design and e-commerce company. It provides hand-painted, illustrated, and digitally-rendered designs for the clothing, beauty, and interior decorating industries. Since 2011, its digital component has expanded to better serve the designers who gather around it - it provides an marketplace, extensive social media integration, a range of e-courses, and a blog with 70,000 readers.

Along with its warm and colorful designer knee socks, it boasts a unique line of products for the season.

Fall Tip: “Summertime for us is all about staying cool and showing a little skin,” said co-founders Kristi O'Meara and Audrey Victoria Keiffer. “During winter, our outfits are hidden beneath tremendous coats. Autumn’s mild afternoons and cool evenings offer us the opportunity to explore the possibilities of our wardrobe by finding new ways to layer our garments and by adding game-changing accessories to our daily looks.”


With a virtual shopping assistant named Jenni, WhatFitsMe keeps track of your size and tastes while you browse for fresh garments. It's a friendly online club for women who get frustrated dealing with salespeople who don't get their senses of style. “WhatFitsMe will help ladies look stylish this fall by helping them find clothes that fit and flatter their figures,” said founder Erica Daly. 

Fall Tip: “For Chicagoans on a budget choose solid color basic clothes and accessorize to add some fall flair,” said Daly.

StylePuzzle is a sharing-economy startup for garment shopping. It enlists fashion consultants to work online with those too busy to hit the racks themselves.

“StylePuzzle works like the Uber for fashion,” founder Liz Li said. “If you are a busy Chicago professional who doesn't have time to keep up with the current fashion, or have no clue how to dress warmly and stylishly, you can easily find a personal shopper on StylePuzzle who shares your same size and style, and can shop for you within your budget."

Fall Tip: “One fall and winter trend I am loving and would recommend is emerald green everything,” said Li. I think it is such a rich color for anything. I’m not a huge fan of green, but there is something about the emerald shade that is so regal and fabulous. So emerald green is the fall color that Chicagoans might want to try out. Royal blue, too.”


Trunk Club is an online membership program devoted to helping men become more savvy dressers. Unlike other similar online continuity programs, there's no signup fee. A personal stylist selects a 'trunk' based on expressed preferences, and the company ships it.

Jason Smith, Trunk Club's VP for merchandising, said that much of his team's work is inspired by the Chicago weather experience. “It is actually the seasonal timeframe that I think our assortment shines the brightest given our breadth of outerwear, sportcoats, and sweaters. Our stylists are exceptional, and they will be teaching our guys to master the art of 'layering' so our members can be comfortable as the climate varies through the season."

Fall Tip: “The mild to cool climates allow you to start having fun with heavier fabrics and weaves,” Smith said. “Fall clothing should be all about texture, and layering that texture appropriately. Tweed, course fabrics, and chunky knits should be coming into play over the next couple of months. If you love wearing stylish clothes, then the fall season is your own personal Super Bowl.”


Threadless is an online e-commerce site and artists' community. Anyone can submit an idea for a new product and compete in a weekly public vote. The Threadless team sifts through the most popular concepts and chooses about 10 to add to its line, rewarding artists with cash and store credit.

Threadless relies on a fiercely loyal online community, but has also gained a high local profile for bringing Chicago's design and tech worlds together, often in its colorful office space. It has a broad selection of clothing for Chicago's perpetual back-and-forth weather.

Fall Tip: And as Chicago quickly transitions from muggy, humid summer to teeth-chattering, slick-sidewalked winter, with barely a nice weekend in between, “make sure you give yourself the ability to pull off or add a couple layers as the temperature inevitably fluctuates from 'hey, winter, let fall have its time to shine' to 'I thought summer was over?', and everywhere in between. Also, layering will help to make the transition from the brisk outdoors to a heated indoor area much more tolerable,” said Threadless marketer Kyle Gelb.

An artisan hoodie looks sharp when you're walking the dog at 30 below, and can be easily stashed in a backpack when it's room temperature ten minutes later.


Inspired by a passion for founder Kate Sanderson's love 'classic cars and retro style,' Sink or Swim launched two years ago. It has the intimacy and personality of a corner botique - all items are handmade in Chicago. But Sanderson's digital presence goes well beyond that of a scattershot Etsy storefront. She sells to the world, and her knack for unique information architecture rivals her color sense.

Naturally, some of her collection is designed for warmth.

Fall Tip: If nothing else, survivors of Chicago's autumn and winter will advise you to layer your outfits. “As most of us know,” said Kate Sanderson, founder of Sink or Swim, “the weather can be unpredictable. Not only can layering look great, but they also can get us from day to night comfortably.”

“Sink or Swim offers fleece lined headbands that not only look stylish, but also keep your ears warm,” said Sanderson. “They also tied up so they can go over any hairstyle, without messing up your hair.”

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