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As summer winds down we reflect on the season’s good times, full of laughter, free-flowing libations, and of course tasteful style. Before we pack away the seersucker and prepare for the return of university courses and autumnal tweeds, we wanted to sit down and reminisce with Mr. Matthew Karl Gale, this year’s winner of the Brooks Brothers’ Annual ‘Dandy at the Derby’ Style Contest.

Ladies and gentlemen submit photographs of their Kentucky Derby-inspired outfits to Brooks Brothers each year during the Kentucky Derby in the hopes of being named ‘dandiest at the Derby’. The coveted title was awarded to a Mr. Christopher Hogan last year. This year the prize went to Mr. Matthew Karl Gale and Ms. Michelle Coursey, who surpassed Mr. Matthew Malecki “by a nose.”

Mr. Gale is a designer while Ms. Coursey is a makeup artist. Both are drawn to vintage fashion. Ms. Coursey, in addition to her work as a makeup artist for runway and celebrity clients, is active in a variety of fields, focusing on editorial and high-end fashion. Mr. Gale is currently leading the design of eyewear collections for Nautica. He was kind enough to grant us an interview with him.

Mr. Gale enjoys a Woodford Reserve Mint Julep

Bickering Ivy: How do you and Ms. Coursey know one other?

Mr. Gale: We met at the Jazz Age Lawn Party here in New York three years ago. We were both modelling 1920s era wool swimsuits for part of the festivities.

BI: How did you get involved in the Dandy at the Derby contest?

MKG: We have searched for a fun derby event in NYC the past few years with little luck. The event at the 21 Club was lots of fun and it provided a great backdrop for our ‘Dandy at the Derby’ portrait.

I am a fan of Brooks Brothers, and when I saw their Facebook contest it was a fun challenge to put together an outfit for the event.

BI: Are you actively involved in the realm of classic style / ‘prep’?

MKG: I am a designer and Michelle is a make-up artist, so we are both involved in creative professional pursuits. We are both drawn to vintage fashion styles from the late 1800s up until the 50s and 60s. We tend to focus on the 20s and 30s. Lately we’ve taken some road trips to visit some of the grand estates along the Hudson Valley.

Michelle has a blog that features some of our social outings as well.

BI: How would you describe your sense of style?

MKG: We both aim for a respectful and polished look. Oftentimes the older styles of dressing — say, wearing a hat or carrying a walking cane — really promote an air of elegance.

Currently I am intrigued by the collegiate look of the 1930s, so striped rep ties, boater hats, and bold colour combinations.

BI: Who have been your greatest influences? Who have been your role models?

MKG: My family has been a great source of sartorial inspiration. While not interested in similar aesthetics, my family has shown me that it’s possible to combine different interests and aesthetics.

BI: What do you enjoy most about your style?

MKG: That it’s evolving!

BI: What advice would you give to those hoping to emulate your style?

MKG: I would caution anyone from emulating anyone’s style directly. However, one basic piece of advice I would offer would be to tuck in your shirt and put on a tie.

Mr. Gale’s website is available makaga.com and Ms. Coursey’s at michellecoursey.com.