Why the Biggest Fashion Enthusiast Has the Smallest Closet

The brand director of Heroine doesn’t need to bring every rare fashion piece home with her. New York.

By: Tara Gonzalez
Styling: Monique Kamargo, Tara Gonzalez
Photography: Alec Kugler

“1994 or 1992” Kristen Dempsey says while talking about a look from a past CHANEL collection. She remembers the fabrics, the colors, and what she loved most about it, but not the exact year. After a long pause, she looks back at me; “I’ll just have to look that up.”

As brand director of the highly anticipated and newly launched resale site Heroine, by the team behind Grailed, Dempsey doesn’t just love fashion, she knows everything about it. And if she doesn’t, she’ll just do the research to find out. I made mental notes of the collections she referenced and decided on the spot that everything I thought I knew about fashion was definitely not enough.

Dempsey is like a fashion encyclopedia, and she describes clothing in a way most don’t. When she picks up a two-piece black Norma Kamali set, she holds the sleeve in the palm of her hand; “This is really thin viscose... She wanted them to feel like butterfly wings.” She hands the top over to me and adds, “It really does feel like that! Look!” She doesn’t just talk about clothing, but she truly tries to understand it. It’s the stories they tell and the way they make us feel that intrigues her the most. It’s also the reason she actually doesn’t keep too much of anything at her apartment in Brooklyn.

“Whenever I go on vacation I feel so great about packing my bag because I feel like I have this amazing little capsule wardrobe. Then I thought, ‘Why don’t I feel excited about all of the stuff that I wear?’” Considering she has racks of incredibly rare finds in the Heroine office, like a Comme des Garçons dress from The Met and a pair of original Margiela Tabi boots, it’s hard to imagine she could restrain herself from buying everything listed on the site—but she does.

At the office she admires pieces she’s always dreamed of from afar, and at home she focuses on comfortable pieces that are “still super beautiful.” Even if her daily wardrobe consists of only a handful of things, she could tell you the fabrics, the year, the designer, and the inspiration behind the collection for everything she owns.

And as I’m about to leave, Dempsey mentions her favorite CHANEL collection again: “It was 1994, by the way.”

Click through to read why she believes a condensed wardrobe is best, what her favorite Miu Miu collection was, and how she’s pretty sure there’s an entity living outside her bathroom.