Brown Elephant Best Of: A Conversation with the Duchess Darling Shear

“Bonsoir” was Darling’s reply to our first email. Right from the beginning, you can tell the Duchess Darling Shear has style. She is a natural performer, a choreographer with an anthropologist’s insight. We got the opportunity to sit down, get to know Darling, and find out why she loves the Brown Elephant Best Of.

Where do you normally buy your clothes? Would you say most of your wardrobe is second-hand or new?

I honestly shop all over. The majority of my wardrobe is vintage, simply because the cuts were new and revolutionary for their time. I appreciate that as a historian.

Yes! That’s part of the idea behind the Best Of, sharing remarkable and important pieces. When you shop, what do you look for? Unique pieces? Classics? Certain patterns or fabrics?

As I am a society woman and public figure, I am often attending events and being photographed, so I’m often looking for a statement piece. I am simultaneously often looking for the perfect minimal piece as well. While I might be looking for a pastel feathered bolero jacket, I’m also looking for a silk cami and crepe wool skirt. But, all in all, I try to not buy things that look similar to other things in my closet.

You have a wide range of tastes! How has your personal style evolved over the years?

I love looking like I should be on a yacht off the south of France or like I have an entire closet dedicated to cream coloured clothing. My style has evolved from looking like the offspring of “Grace Jones & Bjork” to “Diana-post-Charles meets Grace of Monaco meets Eartha Kitt.”

Whether you’re more “Grace Jones & Bjork” or “Grace of Monaco & Eartha Kitt,” find your personal style at the Brown Elephant Best Of, November 4 and 5.

So, professionally speaking, you’re a choreographer. How does style inform your work?

Well, my style doesn’t inform my work so much as my work informs my style. I do historical jazz restaging and reenactments from film and television from the 1920’s to the 1970’s. I’m always researching and being inspired by things that I want to bring into my aesthetic, which is usually not that far off from the things I’m consuming from the golden age of cinema. I’m always looking for costumes that are as close to the original thing as possible because it informs the dialogue of how the performance is presented.

Do you ever alter your clothing for style/fit/etc.? If so, how did you pick up the skills for it?

I do alter things; my size I say is “bigly small,” so things look like they won’t fit but they often do. Every now and then I need to take things in a little or let them out or raise a split to show a little more leg. I am a former fashion designer (and stylish) so I’ve spent much time studying body types and how to flatter them.

You exude confidence. Could you describe an ensemble that gives you confidence?

An all cream outfit with a leopard print pony, fur pump. It just screams “MONEY!”

Let’s talk accessories. Do you have a piece you love to wear regularly? What’s your favorite statement piece?

My statement piece is something I also wear regularly. Pearls. For they are my birth stone and I’ve been wearing them since I was 13; that’s when I got my first pearl necklace. Since then I stockpile pearl necklaces like some women do with Hermes scarfs. I am known for always having on a string of pearls. For I feel they complete every outfit.

Last question, Duchess. Could you describe what “comfort” means to you?

Anything that I can wear for 5 hours before I feel like I wanna fall over.

Don’t miss the Brown Elephant Best Of on November 4 and 5. Shop a curated selection of vintage and high-end clothes, shoes, and accessories from all three of our Chicago-area stores. It’s your chance to find some vintage must-haves, including items from top designers, such as Gucci, Chanel, Balmain, Chloé, Lavin, Prada, and more. All proceeds benefit LGBTQ health at Howard Brown Health. Click here to RSVP on Facebook.

Get better acquainted with the Duchess at


  • This field is for validation purposes and should be left unchanged.
This site is not optimized for Internet Explorer. Please consider viewing the site in a modern browser such as Edge, Chrome or Firefox.