Style & Shopping

Photos: Preakness is a Pedestal for Men’s Fashion

Women are known to turn heads with glamorous hats and sartorial sundresses at Pimlico Race Course, but the fellas' fits are often just as impressive.

When we think Preakness attire, our minds often go directly to the wide-brimmed hats, pastel sundresses, and high heels that grace the grandstand. But men are known to show up and show out for the Charm City horse-racing tradition, too.

“I have photographed the women in hats for years, and they are beautiful,” says contributing photographer Lashelle Bynum, “but I love a sharp dressed man.”

When attending the Preakness Stakes a few years ago, Bynum noticed that some of the men’s ensembles were just as impressive as the female ‘fits.

“I mean, they can really put it down,” she says. “The men spend just as much time and money putting their outfits together.”

So this is Bynum’s tribute to some of the dapper-dressed fellas who wandered around the middle jewel of the Triple Crown this year. Below, she showcases 10 looks—including two worn by trimly tykes—that caught her eye.

Greg George

A Fort Lauderdale native, George dressed in a navy blue striped suit, two-tone blue shoes, and a hat—his “normal everyday dress.” The CEO of Peach Cobbler—a dessert chain making its way to Maryland soon—has been going to the Kentucky Derby for 40 years, and follows the horses on their second leg.

Robert Duckett 

Though Duckett initially had another outfit planned, he went with a backup due to the rain—and it still delivered. He donned purple pants; a multi-colored jacket mixed with paisley and flowers; a blue hat with a blue and gold band; and purple, black, and white Nikes.

Ricky Guyton

“Mr. Ricky” from Crownsville wore shades of blue to his third Preakness. He says his outfit was “just something he had in the closet.”


The Preakness first-timer from Colorado got the memo about Baltimore’s unofficial pink mascot, which adorns green manicured lawns all over town. He purchased the fun flamingo suit and Italian shoes online.

Johnny Cash Emge

Before you ask—yes, his real name is Johnny Cash. The beautiful, brown-eyed three year old wore a beige striped seersucker-looking suit from The Children’s Salon in the U.K., which was accentuated by a gold chain with his initials.

Shawntay Thomas

Thomas spontaneously paired a paisley-printed shirt and pocket square with a blue suit. He says he “threw his outfit on the bed like a bowl of spaghetti and put it on.”


The University of South Carolina Asheville track star celebrated his very first Preakness in a red-and-white suit inspired by his mom. He accessorized with a silver chain and bracelet.

Ben Waldorf

For his first time at Preakness, Waldorf wanted to make his attire “pop.” To achieve this, he paired a white suit with pink shoes and flying pig socks.


It might have been his first time at Pimlico, but the Louisville, Kentucky native knows a thing or two about racetrack regalia. His attire was inspired by the Kentucky Derby’s famous mint julep, and he honored Baltimore with the Oriole bird in his hat.

Leo Miller

The Millers coordinated for their first family visit to Preakness. Baby Leo donned blue striped suspenders, a brown cap, mauve pants, and a blue and mauve shirt.