Written by Case Wiseman

Welcome to Chicago!

Hi, my name is Case Wiseman and I am the Chicago City Lead for TSC.

I would argue Chicago is one of the most iconic urban centers in the world. Nestled along the southwestern shore of Lake Michigan in Illinois, Chicago is known for its rich history and its vital global roles spanning from financial trading to railroad hubs, and, yes, textile manufacturing. So bundle up in your warmest, most stylish coat (you’ll definitely need it), and read on to discover more.

Case and his dog Jay Jay, on a sunny Chicago day testing out the Club Blazer

For many members, this may be their first time experiencing the charm of Chicago. Also known as the "City in a Garden" (Urbs in Horto), Chicago is celebrated for its lush green spaces, including the picturesque 15 miles of Lake Shore Drive. This connection to nature allows the city to breathe, fostering a pace of life that encourages a more thoughtful approach. You might encounter a friendly local offering directions or sharing a hidden gem of the city. When you visit, you'll notice that people take the time to connect.

From Ashes to Ambition

Chicago’s history is all about bouncing back from tough times. Take the Great Chicago Fire of 1871, for example. It wiped out the city’s central business district, left 100,000 people homeless, and caused $200 million in damages. But instead of staying down, the city rebuilt and came back stronger. The fire sparked new opportunities for architects like Louis Sullivan and Daniel Burnham, who came in and shaped the bold architectural style we see today. They emphasized functionality, verticality (Chicago boasts the world’s first skyscraper), and the use of advanced construction techniques.

Then and now comparison of Chicago landscape. Image credit: Bird in the Flight

Crafting Chicago’s Legacy

Chicago architecture’s blend of functionality with beauty mirrors the work of the talented craftspeople who call it home. The concept of “practical elegance” comes to mind when thinking of Chicago-manufactured goods: hardwearing, purposeful, and infused with personal expression. Owning a piece made in the city is owning a piece of history, one that provides glimmers of joy throughout the day you wear it.

When talking about the craftspeople of Chicago, it’s impossible not to mention the legendary Horween Leather Co. For over a century, Horween has been creating some of the finest leathers in the world, and it remains one of the few tanneries still operating in the United States. You’ve maybe heard of Chromexcel, the signature leather developed to be tough enough to be used in war tanks, or Shell Cordovan, a symbol of timeless elegance cherished by shoe aficionados worldwide. Horween leathers are a reflection of Chicago itself: tough, stylish, and timetested. And reaching that goal? It’s complicated, involved, and a sometimes messy process—but it’s all part of what makes it so special.

Hides at Horween factory. Image credit: Ilume Connect

Hats with Soul

Speaking of special, another powerhouse in Chicago’s sartorial scene is Optimo Hats, the world’s greatest hatmaker today. Their manufacturing is on full display on the city’s South Side in Beverly and their storefront is located in the heart of downtown. During my last visit, I was welcomed by Tiffani and Jonathan at the Monadnock Building (which, fun fact, is the tallest load-bearing brick building ever constructed—see a theme here?). As I walked in, sounds of John Coltrane deep cuts played softly in the background, setting the perfect atmosphere for selecting a one-of-a-kind piece. Jonathan walked me through all of the options and points to consider in achieving the perfect trilby hat.

Optimo Hat workshop. Image Credit: Design New City

The Journey to Chicago Starts Here

This introduction is purely a teaser, as there is so much to explore in the vibrant city of Chicago. The Sartorial Club is thrilled to be part of North America’s premier menswear event, the Chicago Collective, taking place this February 1-4. Stay tuned for more updates, in-depth factory tours, and a special black tie dinner in the city on January 31st. I am so excited to share what, I believe, is the greatest city on earth!

(1) Beginnings on the Breeze