The annual 17th Street High Heel Race is all about the participants, the costumes, the characters. The race, while amusing, is a sideshow. The real fun is in meeting the people who show up every year in costume to one of Dupont Circle’s biggest events.
Following is an interview, “A Quick Chat with ‘Anna Wintour,’ ” that profiles one of the Washingtonians who has made the annual Race a big Halloween event, drawing thousands of spectators.
I have known “Anna Wintour,” who I shall identify as “Madame X“–but well known in his real identify to friends and fans–for 10-plus years. Each year I await his Halloween costume to see what persona he will take. This year Madame X is attending tonight’s High Heel Race as Anna Wintour, the longtime editor-in-chief of Vogue magazine–and subject of many articles herself and even a movie or two.
We caught up with “Anna” a couple of hours before the race as she was waiting patiently for the rain to stop. A former resident of Borderstan (The Cairo, early 1990s), “Anna” recounts her favorite characters over the years for the Race and recalls the time she drove from DC to Rehoboth in full drag in her Ford Taurus.
Borderstan: How many years have you been at the 17th Street High Heel Race?
Madame X: I’ve run in the race every year since 1992, when I moved to DC from Puerto Rico. I was teaching school in San Juan.
Borderstan: What personas have you taken on at previous races?
Madame X: Okay, let’s see. There was “The Nanny” (Fran Drescher/Fein), Phyllis Diller, Sidney Biddle Barrows [The Mayflower Madame], Carrie Donovan [Old Navy commercials, The New York Times], Clare Booth Luce, Brett Somers, Nina Totenberg, Bettie Page, Mary Katherine Gallagher,[a Saturday Night Live character, “Superstar”] a Georgetown “house lady” (realtor, that is), Carrie Bradshaw [Sex and the City], model Janice Dickenson, to name a few.
Borderstan: Which persona(s) has been your favorite(s)?
Madame X: My favorite actually wasn’t a particular character at all. Rather, it was the dress that made it my favorite. I found this amazing vintage 1950s ball gown at Meeps [a local boutique] about 15 years ago. Seafoam green with yards of tulle and a sassy bolero jacket. How I miss being able to wear that dress. Every other year or so, I’ll pull it out just to see. But alas, it is not to be.
Borderstan: Which one was the most popular with the crowd?
Madame X: By far, the crowd favorite was Mary Katherine Gallagher. As I marched up and down 17th Street, I would throw myself on the ground to make the audience laugh. I kept doing it so much, for the laughs, you know, I had big gnarly bruises up and down my hips the next day!
Borderstan: Why did you choose Anna Wintour this year?
Madame X: Well, she’s a woman of a “certain age” (kinda like myself!) and she’s in the public eye right now because of the movie, The September Issue. Plus, she gets to wear amazing clothes.
Borderstan: Can I ask how much your outfit cost?
Madame X: Well, I never pay retail, so it wasn’t all that much. Having a good eye for fashion helps when planning your costume each year. That, and daily access to TJMaxx!
Borderstan: I remember that one year, around New Year’s Eve, that you dressed up as a female real estate agent and drove from DC to Rehoboth. Any particular reason you did that?
Madame X: Oh, my. Why, yes, that did actually happen. I was heading out to Rehoboth to surprise some friends. I don’t know what came over me, but I thought, “Wouldn’t it be hilarious to show up out there in full drag and pretend to be a real estate agent?!” So, I got myself completely dolled up in a woman’s business suit, and headed out in my green Ford Taurus to head from DC to the beach. Well, I was so terrified about being pulled over by the police that I set the cruise control at 54 miles an hour and didn’t go above that speed the whole trip. What a fun weekend!
Borderstan: Who is your greatest fashion inspiration?
Madame X: Right now, my greatest fashion inspiration is Chuck Bass from Gossip Girl. I love that he can wear an ascot and make it look sexy and hot.