As Chicagoans gear up to get out of Dodge for the long Memorial Day weekend, one native son—Joliet-raised designer Brian Atwood—is swooping back into his hometown. On May 30, Atwood will appear at a luncheon and talk hosted by the Chicago History Museum's Costume Council, which supports and maintains the museum's hefty collection of historical clothing. (This magazine's editor, Susanna Homan, will moderate). 

The museum is familiar terrain for Atwood, who’s best known for designing soaring and sexy heels worn by the likes of Lady Gaga, Kate Hudson, and Taylor Swift. "I had no idea the History Museum had this extensive of a collection of costumes,” says Atwood, now based in New York and Milan. Ahead of the luncheon, we caught up with Atwood to discuss Chicago’s rich history of style, the local haunts he hits again and again, and the fashion advice he wishes fans would follow before stepping into shoes he's designed.

Do any particular historical periods influence your designs?

It was never one era. There's always that sexy disco woman who's coming out in my designs. But it's pretty much references from instinct and what I love at the moment.

What do you love at the moment?

Well I've always loved—and I'm known for—high heels. I've just always done them, and people have always worn them. I've done some amazing flats that have the same asymmetrical cuts that my pumps have. I think a great sexy flat has to be a staple in your wardrobe, like a basic pump.

That’s perfect style advice for Chicago, which is such a walking city.

The Chicago customer loves fashion, from the athletic part of it—running on the lake—to the fashion part of it. My mother [Dusty Stemer] and her friend Toni [Canada], they also demand that Chicago is not just some Midwestern "in the heartland" city. It's a taste-maker level city, and it has a voice in fashion.

What are your favorite local shops?

I admire Ikram and Blake. Chicago has had some of the best stores. Ultimo, when it was open, was rivaling the best stores in the world.

Apart from hitting the boutiques, what are some other must-dos when you’re in town?

There are so many beautiful museums. The Art Institute, with the Renzo Piano [Modern Wing] is just beautiful, and Millennium Park is great. My parents have a house close to there and we walk around and go the Art Institute, and then really just walk around and see what's going on in the city. 

My favorite restaurant changes all the time. Le Colonial is always a favorite, and Weiner Circle late nights with my brother, always.

What's the piece of style advice you find yourself giving most often?

Know if a trend is right for you, and know your body type. When it comes to shoes, know what heel height you can walk in, and if you've never walked in [a particular style], practice at home. Wear them around the house. Nothing is more painful than watching a woman either not know how to walk in heels or in pain in her shoes because her heels are too high.