buying an optimo


While proud to call Chicago home, we sell all over the world.

If you can't come in to our downtown store, no problem. More than half our business is out of state and International. 

We perform fittings in our shop, at trunk shows, and over the phone. Regardless of where you are fitted, our focus is on creating the right hat for you.



First time Optimo client.

Before purchasing your first Optimo, it is important that we have a short discussion. Whether over the phone, online, or in our store, we must ensure your correct hat size and a style which suits you.

Contact us to set up appointment.

Purchased from us before.

We keep records of your Optimo collection as well as service history.  Let us know what you are interested in — a certain color, or style and we can guide you in the right direction.  


Phone and online fittings.

The best way to prepare for a fitting is to get an idea of the style you want. You don’t have to supply us with all the details. We will help guide you. Please visit our website to view various styles. Consider the design elements in hats you have seen and admired in films, hats worn by celebrities or hats from specific time periods.

Have a soft tape measure handy so we can guide you through our measuring procedure.  Our fit video is a tool for this. 

We will also ask you about your lifestyle, facial features and the types of clothes you favor. If you are a seasoned hat wearer, please note the style, sizing and fit of your other hats so we can improve on any fit or style issues you may have had in the past.


Your fit.

A properly fitted hat should be comfortable to wear for hours at a time, in any situation. Your hat should gently grip your head just above the ears, and be able to be pulled down a bit more, making the fit tighter when it's windy—something we know about in Chicago!

To achieve a customized and truly personal fit, our hats can be custom ordered in three sizes between the conventional sizes, as well as in four oval head shapes in order to achieve Optimo’s unique ‘air cushion’ fit.



Your Optimo is much more than a fashion statement— it's your companion for life.


Life's better in a great hat.


Optimo was founded 25 years ago in a small shop on the South Side of Chicago, one of the rare places in the world where an appreciation for great hats never died.  Our 'veteran' South Side clients were instrumental to the success of our business, helping us to understand what a 'real' hat should look like and how it should perform.

Our client base has since developed into a global family, including musicians, businessmen, architects, tradesmen, professors, doctors, policemen, politicians, chefs, actors, creatives and many more.

Optimo enthusiasts are not defined by their professions, but by their shared appreciation of quality, individualism and style. They see their Optimos as something much more than a fashion statement. It's a part of their life.

Our clients are the richest parts of our business, our most stalwart fans and an endless supply of inspiration and motivation.



A business is only as good as it's customers and we have the best.