At 22, Graham Thompson was worried about a very important thing: Chicago’s hat making industry.

While hipsters zipped around Chicago town wearing cheap and mass made fedoras they got at trendy chain stores, Thompson knew they didn’t compare to the hand-made hats custom produced by craftsman in the South Side of Chicago, whose customer base had been shrinking since hats fell out of style in the 1960s.

So Thompson asked Johnny Tyus, a legend in Chicago hat making, to teach him the trade.  Thompson took those lessons and opened Optimo, which has locations in both Downtown Chicago and the South Side Chicago, and once again is making custom hats for Chicago and visitors to the Windy City.

The process can be an long one, but stick with it: they’ll measure your head, have you try on hats in different shapes and styles, and then refine the shape for you, including length of the brim, the height of the hat, size of the ribbon, and, of course, the color.

Then the hat is custom made, typically out of wild fur or straw, depending on if you’re shopping for warm or cold weather, to those specifications. The fur is key – the color won’t run or bleed. Plus, Thompson learned from studying old, well worn hats that they hold up best in the rain or snow.

Not impressed yet? Here’s something you won’t find in mass made hats: each one includes include a roan (sheepskin) sweatband, and all linings are hand sewn. The process takes about a month, though if you’re impatient, they will sell you one of the hats that line the walls and windows of the store.

Prepare your budget, though. Optimo hats are a splurge. But if you’re visiting Chicago and need a hat, start saving. You’ll never need to replace it.