Excellent Chicago Fashion Insights to Make an Impression | Part 3

Updated: May 27

We have shown you some of the best nightlife that Chicago has to offer but if you want to look great while on the dance floor, then look no further! Here's our guide to the best of Chicago fashion.


Chicago's Best Luxury Shopping Experience

In our last couple of posts, we covered dating and nightlife. And now, we turn to fashion. A quick Google search of “Chicago fashion” could very well result in a long list of North Face coats and Patagonia long underwear - spoiler alert, it can get pretty cold! However, Chicagoans accept the intense winter (and summer) weather as a challenge to look classy in spite of extreme temperatures. In fact, embracing this unique climate has yielded some Chicago-based luxury fashion trends even New York and LA can agree are on point.

So let’s kick it off with the Gold Coast. This historic neighborhood, one of Chicago’s most affluent areas, is a popular destination for high-end shopping, especially around Oak Street. This is where you’ll find charming, tree-lined streets dotted with luxury boutiques and couture showrooms, all just steps away from Michigan Avenue.

Right on Oak Street, you’ll find outposts for some of the world’s top designers, such as:

  • Giorgio Armani

  • Prada

  • Chanel

  • Dolce & Gabbana

  • Escada

  • Christian Louboutin

  • Hermes

And you can also find one-of-a-kind gems in Oak Street’s luxury boutiques:

  • Morgenthal Frederics

  • St. John Boutique

  • Wolford Boutique

  • Tod’s

  • Loro Piana

  • Vince

A well dressed man covers his face with a hat

If you’re looking for jewelry,, the Oak Street District is home to some of the finest luxury jewelers and timepiece boutiques available in Chicago, including Richard Mille, Patek Philippe by Razny Jewelers, Rolex by Razny Jewelers, Harry Winston, Graff, Geneva Seal, and Buccellati. Located in the heart of the downtown area, Oak Street District is the premier destination for luxury accommodations, superb fine dining, exquisite high-end salon and spa experiences, and exceptional boutique shopping at the world’s most sought-after fashion houses, blended together to create the finest luxury Chicago experience just for you.

Nearby on Rush Street, you can stop into Christian Dior and Versace. And don’t miss the Yves Saint Laurent hidden inside the Waldorf Astoria Chicago on Walton Street. While you’re there, take a minute to admire the hotel’s glittering lobby chandelier, which was inspired by the vintage jewelry designs of Coco Chanel and Christian Dior.

And while you’re in the area, be sure to take in these vintage and historic attractions:

  • Museum of Contemporary Art: Wander galleries filled with the latest in contemporary art and grab a bite at Marisol, the museum’s acclaimed restaurant.

  • Chicago Sports Museum: Test your skills against the world’s sports greats at this interactive museum, located on the 7th floor of Water Tower Place.

  • City Gallery at Historic Water Tower: This gem of a Gothic Revival building survived the Great Chicago Fire. Today, it’s home to fascinating rotating art exhibits.

  • Driehaus Museum: Relive Chicago’s Gilded Age at the former Nickerson Mansion, known as Chicago’s “Marble Palace.”

  • Newberry Library: Take a look at a vast collection of rare books, maps, music, and manuscripts, spanning more than six centuries at this architecturally stunning research library.

Top Fashion Tech Companies in Chicago

While Chicago may not be the first place that comes to mind when you're thinking about fashion, the Windy City punches way above its weight in the fashion tech vertical. The Chicago tech ecosystem has pioneered the at-home personal shopper experience, and is also responsible for bringing consignment shopping to new audiences and creating new ways to customize clothing. Check out how these companies are making their mark on the fashion world.

Fit Analytics

Based in Berlin and Chicago, Fit Analytics is comprised of a team of data scientists, fashionistas, physicists, designers, and hackers, working together to tackle one problem: making it easy for online apparel shoppers to find their size and fit.. They're helping some of the world's largest apparel firms solve sizing issues and boost conversions.


GoodPix is a cool platform that helps fashion companies and blogs to monetize their product recommendations through shoppable content and virtual storefronts. The company gives side hustlers the tools to launch their own customizable fashion site in a matter of minutes, and then supplies them with the tools they need to make money off of their content. GoodPix has partnered with global brands, like Nike, Anthropologie, and Zappos to help fashion entrepreneurs get a head start.

Bamboo Supply Co.

Bamboo is a delicacy for pandas, but fun fact - it can also be used to make delicates! Who knew? Chicago startup Bamboo Supply Co. uses bamboo fiber, known for being breathable, soft and odor-resistant, to make socks, underwear, sweatshirts and sheets. In addition to its regular e-commerce platform, the company offers a “sock of the month” subscription service, which, indeed, is exactly what it sounds like.


For bridal parties who are scattered all across the country, picking out matching bridesmaid dresses can be quite a big 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. Bridesmaid shopping made easy!


Bucketfeet turns your feet into a walking canvas for artists all over the world. The company’s designer network, which consists of over 40,000 designers, photographers, and artists from over 120 countries, can submit new designs through its online platform for inclusion in the company’s next collection. Designs are then voted on by consumers, with new limited edition products coming out every month.


What if you could buy new clothes and apparel simply by clicking on the images on your favorite fashion blog? Well, look no further than LOOKCAST! The company creates interactive lookbooks that generate advanced engagement metrics, helping creators of fashion content monetize their audiences.

Luxury Garage Sale

What if online consignment shopping could be as curated of an experience as perusing an upscale department store? That is the question that motivated the founders of Luxury Garage Sale to get their empire off and running. Founded in 2011, the company has raised $8 million in funding and opened up several brick-and-mortar stores that help source inventory for its online marketplace.


Do you ever feel like the “recommended for you” pieces that you see while shopping for clothes online is way off the mark? That’s probably because they frequently rely on manually tagged keywords to discover similar items. Riviter is a website widget that uses image recognition to help customers hone in on items that appear similar to the ones they were looking at. Although still in the early stages, Riviter was a finalist in the University of Chicago’s New Venture Challenge in 2016.

A couple of luxury suits with bold tie combinations

The Tie Bar

Ties, despite their size, can be surprisingly expensive. And thus, The Tie Bar was born. It was founded in 2004 to make handmade silk ties more affordable online. Since those humble beginnings, the company has expanded to offer pocket squares, socks, belts, cufflinks and other accessories - and there’s a rumor going around that they’ll start making shirts as well.

Chicago's Fashion Incubator

The Chicago fashion scene is quite busy, and it’s not going away anytime soon. The Chicago Fashion Incubator (CFI), located in the Pedway of Macy’s on State Street, provides emerging Chicago-based designers with resources, including work space, mentoring, and workshops, to help them blossom in their fashion careers. Workshops range in topics from media training, creating business plans, cost analysis, and building a brand strategy to more artistic sessions like preparing patterns for production to color and proportion theory. Throughout the program, the designers have the opportunity to establish relationships with a network of industry professionals including lawyers, accountants, fashion buyers, merchandisers and branding, marketing, and communications experts.

While CFI’s offices and workspaces remain closed due to COVID-19, the Incubator continues to provide robust programming as well as mentoring for both its current and alumni designers. However, CFI’s public events, which include expert panels speaking on a variety of fashion industry-related topics, have unfortunately been put on hold for the time being.

“Although we certainly wouldn’t have chosen to welcome in our new designers during a global pandemic, our Board is proud of CFI’s ability to pivot to remote programming, ensuring that all of our designers won’t lose valuable time as they work toward developing their fashion lines,” said Andrea Schwartz, CFI Board President.

“In the weeks since CFI’s facility has been closed, our Director of Programming and Events, Anna Hovet, has arranged informative seminars with fashion leaders and influencers – including an editor from Vogue – as well as invaluable mentoring sessions with industry pros like David Sanchez of 10 MGMT and seasoned designers like Nora Jewett and Alice Padrul. COVID-19 has certainly not stopped us from providing our designers with educational programming that can’t be found anywhere else in Chicago!”

The Bottom Line

It may not jump to the top of your mind as a central hub of fashion, but as you can see, Chicago is certainly doing big things. Whether you’re looking for a luxury shopping experience or want to explore upstart trends, Chicago has it all when it comes to fashion.

At Kahana, we live and breathe content creation. We love learning new concepts, exploring emergent trends, and writing about topics that foster creativity and wellness. If you're interested in writing with us or would like to collaborate for your dream business blog, we'd love to hear from you!

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