9 Fashion Tech Companies Keeping Chicago Classy

Chicago may not be the first place that comes to mind when you're thinking about fashion, but the city punches way above its weight in the fashion tech vertical.

Written by Andreas Rekdal
Published on Nov. 16, 2023
9 Fashion Tech Companies Keeping Chicago Classy

Chicago may not be the first place that comes to mind when you're thinking about fashion, but the city punches way above its weight in the fashion tech vertical. In addition to pioneering the at-home personal shopper experience, the Chicago tech ecosystem is responsible for bringing consignment shopping to new audiences and creating new ways to customize clothing.

Top Fashion Companies in Chicago

  • Brideside
  • Nordstrom Trunk Club
  • The Tie Bar
  • Threadless
  • Stock Manufacturing Company
  • Luxury Garage Sale

 

Here's how Chicago tech companies are shaking up the world of fashion.

 

The Black Tux gives consumers in need of suit and tuxedo rentals the option of shopping online or in-person at a showroom. Its online customers select their formalwear options and then provide details like their height and weight to get size recommendations from the company’s fit algorithm. The Black Tux also has specialists who review orders and are available to answer sizing questions.

 

Originally conceived of as a boutique service for men who want to dress well but don't care for shopping, Trunk Club has since expanded to styling up women as well. Upon signing up for the service, shoppers will be connected with a personal stylist to talk about what they like and don’t like to wear. The stylist then picks out a collection of items that the shopper can try at home, with the option of returning anything they don’t like. Since its launch in 2009, Trunk Club has become a pillar of the Chicago tech community, with hundreds of employees in the heart of River North.

 

For bridal parties who are scattered all across the country, picking out matching bridesmaid dresses can be a major hassle. Brideside wants to remove stress from the process by letting professionals handle most of the legwork. After signing up for the service, the bride-to-be is paired with a style consultant who works with her to pin down an aesthetic. The consultant then works with each bridesmaid to pick three dress styles she can try on at home. After finding the right fit, she can order it online in the right material and color.

 

What if online consignment shopping could be as curated of an experience as perusing an upscale department store? That is the question that drove the founders of Luxury Garage Sale to get their empire off the ground. Founded in 2011, the company has raised $8 million in funding and opened several brick-and-mortar stores that help source inventory for its online marketplace. But Luxury Garage Sale is doubling down on its tech roots too: after relying largely on outside developers since launch, the company announced this summer that it is bringing its techies in-house.

 

Supporting your favorite sports team doesn’t necessarily mean you have to wear baggy and unflattering clothes. Sporty Threads creates fan apparel for women who want to stay in style while tailgating or celebrating the big win. The company was founded in 2012 and sells gear to fans of professional football, basketball, baseball and hockey, as well as for a number of collegiate teams.

 

Looking to support the local manufacturing scene? E-commerce sensation Stock Manufacturing Company sells fashionable menswear that’s built to last. The company’s products are all handmade in Chicago, and have been featured in publications like Esquire and GQ.

 

Perusing thrift store after thrift store is a great way to spend an afternoon, but it’s not as easy as shopping from your desk. Headquartered in Bolingbrook, Swap.com is America’s largest online consignment store, offering more than 1.5 million garments, games, toys and baby gear. And with a total of over $10 million raised last year, the company is sure to only keep growing.

 

Considering their simple design and the small amount of fabric involved, ties are surprisingly expensive. The Tie Bar was founded in 2004 to sell handmade silk ties more affordably online. Since those humble beginnings, the company has expanded to offer pocket squares, socks, belts, cufflinks and other accessories — and rumor has it the company is about to start making shirts as well.

 

Why should in-house designers have all the fun? Founded in 2000, Threadless lets its customers vote for user-submitted designs that the company then puts on shirts, hoodies, blankets, tapestries and pretty much every other kind of textile you can imagine. Once a piece has been put into production, designers get a cut of the proceeds through PayPal. Users can also submit designs for co-branded merchandise for franchises including Marvel, Star Trek and Back to the Future.

This article was originally published in 2016. Rose Velazquez contributed reporting to this story.

Hiring Now
McDonald's Global Technology
eCommerce • Food • Information Technology • Mobile