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Menswear isn’t just for the boys anymore. Whether you want to rock the boyfriend look from head to toe or complement a floral dress with a well-structured blazer, he-for-she style is flattering for just about every body type. These five Chicago boutiques teach us how it’s done.

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denim lounge

The Denim Lounge
Go for: Boyfriend jeans

Enter the Denim Lounge at your own risk. Last time we walked in, it was all but impossible to leave with less than five new pairs of jeans (and we’re still dreaming about that sixth). The experienced stylists help you make sense of the shop's 15-brand selection, finding you the perfect fit while still keeping comfort, durability and wash in mind. And lucky for the menswear maven, there are plenty of distressed, boot-cut and boyfriend-inspired styles to choose from.

2039 W. Roscoe St.; 773-935-2820 or Facebook

milk handmade

Milk Handmade
Go for: Smart, structured blazers

Everything in this cozy-chic Andersonville boutique feels special—and that’s because it is. Owner Hallie Borden selects strictly handmade wares to stock in her shop, and the result is an inventory so dreamy, you’ll want to renounce the outside world. (The resident greyhound, Sauvie, doesn’t hurt either.) We’re in love with everything, but especially the blazers: perfectly cropped and patterned with a playful touch of unabashed femininity.

5137 N. Clark St.; 773-234-7053 or

una mae

Una Mae’s
Go for: Street- and surf-inspired style

Walk into this Wicker Park storefront, which serves both men and women, for a serious dose of coastal cool. It even smells like the beach in there. But we digress: The slouchy hats make the ideal accessory for the lazy Sunday flannel-and-leggings ensemble that we like to think of as Ron Swanson-chic. P.S. Don’t be afraid to venture over to the fella’s section. With leather watches and offbeat button-ups, you can snag some actual menswear and make it all your own.

1528 N. Milwaukee St.; 773-276-7002 or


Lori’s Shoes
Go for: Oxfords, sneakers and combat boots

Shoes! So. Many. Shoes. With just about every style under the sun, Lori’s is your go-to for everything from stilettos to slippers. We’re especially digging the plethora of sleek, utilitarian offerings currently available. Some of our favorites include slip-on sneakers and the functional yet fashionable fur-lined boots. Yes, winter is coming. Sorry to remind you.

824 W. Armitage Ave.; 773-281-5655 or

penelope s

Go for: Oversize outerwear

This ultra-elegant Ukrainian Village spot strikes the perfect between Scandinavian chic and all-American cool. With a simple but sturdy structure, Penelope’s oversize dolly coats capture everything we’re loving about the menswear trend. Plus, we’re pretty sure these boyfriend sweaters and camel-leather backpacks were taken straight from our Instagram overlay dreams.

1913 W. Division St.; 773-395-2351 or

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