About

We started Southside Custom Hats on the belief that a hat should do more than complete an outfit, it should express something genuine about the person wearing it, whether your style is classic, cowboy or modern bohemian (or a combination of the three). 

We believe that there is a hat for every person, we just need to discover it together, and there wasn't a place in Chicago for a person to do that.

We approach every piece with attention to proportion, materials, fit, and the details that give a hat its character. Whether you choose an available one-off or commission a custom build, the aim is the same: a distinctive hat that feels considered, personal, and made for real life.

Built with intention

Durability matters. We select quality felt and construct each custom hat with the expectation that it will be worn, cared for, and enjoyed over time. We want your hat to last a lifetime, and grow with you, with each ding and mark telling a story, not be something you throw out a year later to just be replaced with something new.

Shape, trim, and finish are considered as part of the whole—not added as an afterthought.

Personal style, properly fitted

Style is most successful when it belongs to the wearer. We look at more than hat size, considering facial features, proportions, wardrobe, lifestyle, and personal taste to find the right balance of crown, brim, color, and detail.

An investment in craftsmanship

A custom hat represents quality materials, skilled work, and thoughtful decisions made one at a time. It is an investment in a piece that can become part of your signature style rather than a temporary addition to your closet.

Explore Southside Custom Hats

Browse our One-Offs to see finished pieces, learn about commissioning a piece on the Custom Hats page, or contact us to begin a conversation.