Best Places To Buy A Hat In Chicago

When it comes to the coming Midwestern chill, remember — green, brown, black or white — to keep that hat pulled down tight. Even if you think you're not a "hat person," fall and winter in the Windy City will have a way to make you into one. Berets, beanies, bowlers, buckets or beavers (faux, natch) are waiting to cover your crown at these fine Chicago hat shops.

(Photo Credit: Hats Plus Ltd.'s Facebook)

(Photo Credit: Hats Plus Ltd.'s Facebook)

Hats Plus
4706 W. Irving Park Road
Chicago, IL 60641
(877) 428-7863

An independent shop not in a trendy neighborhood? Hats Plus offers a colossal selection of styles and colors, non-hovering yet extremely knowledgeable staff and zero attitude to make shopping for your next lid a pleasant experience. Get your Stetson Belfast Fedora, Kangol, Pork Pie or Dobbs and a nice hat box to tote it home in. There are well made hats for women, too, but not nearly the selection as for the XY chromosome set.

Goorin Bros. Hat Shop
1533 N Milwaukee Ave.
Chicago, IL 60622
(773) 384-4287

In its fourth generation, Goorin Brothers specializes in family craftsmanship and boasts a staff with an encyclopedic knowledge of size, color, style and brand. Shop by shape (trucker, bowler, pillbox, Panama, etc.); lifestyle such as sportsman or artsy; and what's new in the world of flatcaps, cadets, ball caps and fedoras. Good bets for fall are floppy hats, cloches and fedoras in wool. Goorin Brothers also has an outpost in the Lakeview neighborhood.

320 S. Dearborn
Chicago, IL 60604
(312) 922-2999 

The piece de resistance of lid land, Optimo is the home for a made-to-order hat for your particular dome. If you want cheap, head to a department store. A hand-made hat from Optimo is more of an investment than a mere coverlet for your cranium. The staff will gladly tell you if you're looking a fool in a particular chapeau and steer you to a style that works in terms of style and warmth.

Related: Ask A Chicago Expert: Tips On Finding Deals Shopping Online

Sid's Clothing and Hats
609 W Roosevelt Road
Chicago, IL 60607
(312) 421-3332

The visual epitome of old school, Sid's is a beacon for the noggin in University Village. In fall, you can snag a nice discount on summery, premium Borsalino, Stefano, Dobbs, Ecuadorian Panama straws and Stetson straw hats. As Chicagoans are well aware, winter requires serious coverage and Sid's offers an array of shearling Aviators, fur Trappers, crown leather Envoys, a pricey designer-made, pure beaver fur felt hat or, on the other end of the cost spectrum, a sturdy, pull-on skull cap.

Chapeau Creations
9535 Keystone Ave
Skokie, IL 60076
(847) 213-0303

When you need a topper for the lady, the designers at Cheapeau Creations can do it to your specs or, for less money, you can choose among a fine selection of ready-to-wear. Fall/winter headgear is bold, unique, yet efficient against the Midwestern elements. Consider a wool beret with a kitchy hand-beaded pocket watch trim or a soft furfelt with inlays of felt in contrasting colors. The Chicago shop, designing millinery for over a quarter of a century, also specializes in special occasion hats – think weddings and the Derby.

Related: Best Places For Handmade Accessories In Chicago

Jacky Runice has been a columnist with the Daily Herald Chicago since grunge music and flannel was the new black. Her fingers and gray matter have been busy as travel editor of Reunions Magazine; penning a column that was syndicated around the nation via Tribune Media Services. Her work can be found at