Find Your Perfect Hat to Brave the Cold


Winter is here, time to dress appropriately. And that includes the right hat. Here are some of Chicago’s coolest places to shop for the perfect headpiece.


Set in one of Chicago’s most iconic buildings, the Monadnock, Optimo is a must-visit shop when wandering the Loop. Graham Thompson, who founded the storefront 25 years ago, traveled around the world in search of the finest materials and machinery, dating all the way back to the golden age of hat-making. When you buy a hat here, you’re family…

51 W. Jackson 


40 E. Oak – by appointment only call 312-640-6004

If you’re looking for a truly unique headpiece, make an appointment with master milliner Loreta Corsetti. Inspired by the past (think Italian Renaissance, Art Deco, and more), Corsetti has been creating unusual headwear for over thirty years. Her masterpieces have been photographed by the best and featured in countless magazines.


609 W. Roosevelt 

Sid’s is a mom & pop shop where you’ll find both a fine selection of men’s clothing and over 10,000 hats and caps — ranging in style from felt fedoras to cowboy. 

SPACE 519 

200 E. Chestnut 

When it opened in 2010, Space 519 was the very first fully integrated, European-style, concept store in Chicago. This mecca for connoisseurs of the good life is home to some of the most stunning items. Everything is carefully curated by owners Lance Lawson and Jim Wetzel. The pair focuses on women’s apparel and accessories, green apothecary, inspired home goods, unique books, and gifts with themes, ideas, and motifs inspired by their travels. 


1733 W. Chicago 

Looking for a piece of Texas in Chicago? Saddle up your horse, gallop to Alcala, and we guarantee you won’t be disappointed. Founded by Luis Alcala in 1972, this family business houses roughly 5,000 different hats and 8,000 pairs of boots, making it one of the largest retailers of Western wear in the Midwest. Yeehaw! 

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