By Jonathan Sigmon
Hats have garnered something of a bad rap in the modern era, seemingly rising and falling in popularity by association with some less than inspiring trends. It can be difficult for the hat-hesitant to come around to the joy of a good hat when there are few stylish folks around as inspiration. For years I was one of those folks – interested in the idea of fine hats, but always feeling like I was wearing a costume when I put one on. I slowly shifted my perspective by seeing a few stylish people wear their hats in ways distinctly unique to them. A couple that come to mind include Dr. Andre Churchwell, who wears any and all style of hat with aplomb, and Ethan Newton of the Brycelands store in Hong Kong, who pairs his felts with often vintage and workwear-inspired tailoring. A more under-the-radar custom shop client and consultant for Optimo finally pushed me into it with his own insouciant hat-wearing flair, and his recommendation of an Optimo Montecristi Teardrop a couple of summers back.
Operating out of a restored fire station in Chicago’s South Side, Optimo is considered by many to be the best hatmaker in the world. Optimo’s owner Graham Thompson is a lifelong student of the craft, having honed his skills over thirty years of studying old-school milliners and sourcing vintage machinery to make his hats as they were made in the heyday of the early-mid 20th century.
During a Spring trunk show in Chicago where I posted up in Optimo’s retail shop in the South Loop, I bought one of their more interesting recent developments – a foldable travel hat dubbed the Mundo. This Beaver felt model is customizable into several shapes, depending on one’s mood any given day, and rolls up into itself for tucking away during travel. Optimo’s felts are uniquely special in that they are highly malleable, while still being strong enough that they won’t lose their shape. (For a thorough overview of their felts and hat-making methods, have a look at the site.)
After a couple summers wearing my Montecristi panama with all sorts of clothing, I’ve learned my preferred style is wearing these fine hats with more casual clothing. You’re unlikely to find me in a full suit and tie with my panama crowning my head on a Summer day, as it’s a more dandified look than suits my personal style. I enjoy pairing it with linen trousers or shorts with a camp-collar shirt, or one of our bespoke square hem sport shirts untucked and cut on the easy side. I tend to wear my felt Mundo with outfits like jeans and our knitted slack jacket, and most recently with a shetland sweater at a backyard dinner during an unseasonably cool evening.
During that Chicago trunk show, while I was hosting clients in Optimo’s South Loop showroom I was struck by how similar their approach is to our own process of guiding and educating prospective clients. All manners of individuality are considered – how one likes to dress, their hair/skin complexion, where and how the hat is likely to be worn. I resonate strongly with like-minded retailers and craftsmen who aim to guide their clients to get the most satisfaction from the goods they specialize in. Perhaps more than anything else, that’s why I’m glad to have developed a friendship with the team of one of the best hatmakers in the world.
