Le Dress

Division is quickly becoming one of the hottest streets of Chicago style and adding to the appeal is Le Dress. The charming boutique, owned by sisters-in-law Eva and Robyn Anderson, stocks frocks from the likes of Shoshanna, Nina Austin and its own eponymous label. A girl could outfit both her work wardrobe and after-hour attire from one rack alone—and many have been known to do just that. The fashion following has only just begun.

1741 W. Division
(773)697-9899
ledresschicago.com

Audience choice:
p+L boutique
2956 N. Clark

(773)248-3758

Best of Chicago 2008

Haberdash

One look at owner Adam Beltzman and you’ll see why Haberdash has quickly become one of the premier men’s boutiques in Chicago. Sophisticated but not overstated, confident but not pretentious and perfectly accessorized at all times, Beltzman quit his day job as a lawyer a few years ago and has never looked back. Haberdash is a store with a Midwestern practicality for regular guys who just want cool clothes that fit well. Is it really so much to ask? The answer here is no, where collections by Donald J. Pliner, Nicholas K. and Loomstate abound…to the delight of fashionistos citywide.

1350 N. Wells
(312)440-1300
607 N. State
312.624.8551
611 N. State
haberdashmen.com

Audience choice
p+L boutique
2956 N. Clark
(773)248-3758

Best of Chicago 2008

Hats Plus

This warehouse at Irving Park and Cicero has had the Chicago market cornered in men’s headwear since it opened in 1987. With a stock of more than 30,000 hats to choose from, you’ll find the perfect Stetson, fedora, pork pie, newsboy or Kangol made from leather, cloth, fur felt or wool. If by some slim chance you can’t find what you’re looking for, the good folk at Hats Plus will oblige you with custom work as well.

4706 W. Irving Park
(773)286-5577
hats-plus.com

Audience choice
p+L boutique
2956 N. Clark
(773)248-3758

Best of Chicago 2008

Lenny and Me

This popular resale/consignment shop in Wicker Park is known for its quirky vintage wares. In addition to eclectic clothing and jewelry, Lenny and Me offers a selective array of classic and contemporary women’s hats. The shop sells a rotating collection of twenty-five to thirty hats on any given day: “church lady” pillboxes, wool caps, fur-lined bombers and beautifully crafted vintage cloches. But if you’re looking for something to wear to a Cubs game, you’ll have to go to Lids; at this kitschy hipster shop, there’s nary a baseball cap in sight.

1459 N. Milwaukee
(773)489-5576
lennyandmechicago.com

Audience choice:

p+L boutique
2956 N. Clark
(773)248-3758

Best of Chicago 2008