Windy City Headwear

Custom. Western. Hats

What we Offer

We create custom, handcrafted cowboy hats that blend quality, style, and affordability. Each hat is designed to reflect your personal taste, whether you’re looking for a classic Western look or something with a modern twist. Our process allows you to choose the color, shape, and details that make your hat unique.
With a passion for craftsmanship and a love for Western fashion, we make it easy for you to own a high-quality, custom cowboy hat without the high price tag. Whether you’re dressing up for an event, heading to a concert, or simply adding to your everyday style, we’ve got the perfect hat for you.

Every hat is thoughtfully designed and crafted with care to match your unique style. Whether it’s for everyday wear or a special occasion, our custom hats are made to feel personal and one-of-a-kind—just for you!

Create Your Favorite Hat

Today!

Local Customization

Custom Hats by Appointment

We currently offer personalized custom hat designs, created just for you. All appointments are held Online or in Chicago, Illinois, where we take the time to craft a unique piece that fits your style.
For now, our process is by appointment only. Please see the Inquiries tab and fill out the form!

Contact Us to Schedule Your Appointment:
📞 630-702-9204
📧 windycityheadwear@outlook.com

For Your Next Event

We’ll Bring Custom Hat Design to Your Next Event!

Looking for a unique and unforgettable experience? We’ll come to your event and create custom hats for your guests. Perfect for parties, weddings, or corporate gatherings!

Local Events Preferred – Chicago area or locations that are easy to reach.

Let’s make your event one to remember with personalized cowboy hats for everyone!

Bachelorette Parties | Weddings | Private Events