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One of Our Men of Style: Derek Fleming

By Luis R. Rigual | March 27, 2020 | Style & Beauty

Sartorial finesse defines these miami gents. A closer look reveals the personalities behind all that panache. Next up, Derek Fleming



Real estate developer, community builder and entrepreneur Derek Fleming has revitalized neighborhoods in San Francisco, New York and New Orleans, but lately he’s set his sights locally. The newcomer is currently overseeing a development in Miami’s historic Overtown neighborhood with the hopes of bringing interest to the often-overlooked community, and he also happens to be a managing partner in Red Rooster Overtown, star chef Marcus Samuelsson’s first restaurant in Miami. With a demanding career, a partner of 20 years and 7-year-old twin boys, life is busy to say the least. That’s why Fleming embraces style that’s versatile. “My friend Mayra and I call it calculatedly casual,” he says. “You can leave work, head to the bar, then to the hottest club in town in the same outfit and never skip a beat.”

What’s your fashion philosophy? To stay away from trends and strive to be classic and timeless.

What’s your approach to dressing? I try to reflect my mood in what I wear.

What’s the most cherished piece in your wardrobe? I love my cinnamon full-length shearling coat with sheep’s fur lining. I can pop it on with sweats while hanging out with my twins, over jeans while running errands or on top of a suit for an evening out with my partner, Sonny.

What are your favorite brands? I like Calvin Klein for the simplicity, comfort and clean lines, and I like Tom Ford for his sexy and luxe approach... bold without being overindulgent.

Do you recall a big fashion moment in your life? Yes! Wearing a honey faux-fur sleeveless vest to see Prince perform at Webster Hall and landing onstage with my idol.

Complete this sentence: A man is not fully dressed without... confidence. That’s more important than any outfit.

Photography by: Nick Garcia | styled by Danielle Parents | shot on location at W South Beach