2023 Preakness: Baltimore stylists on what to wear to Pimlico to turn heads on race day

On Preakness day at Pimlico Race Course, the sightseeing rarely disappoints.

Neither does the fashion.

The second leg of the Triple Crown takes place May 20 in Baltimore. Visitors will eat crab, drink Black-eyed Susan cocktails, make wagers, cheer on favorites and most of all — show off their sense of style.

“This is the time, because it is Preakness, to have as much fun with fashion as you can,” said Christie Vazquez, the owner of Brightside Boutique, a women’s clothing store in Baltimore. “What better time?”

Hats in elaborate shapes, sizes and shades typically steal the show. But this year, one local designer predicts they’ll be turned on their head. Drop-waist dresses are in, according to another, and menswear is leaning more casual.

Here’s a look at what’s hot — and how to stay cool — for the 148th Preakness Stakes.

It’s the year of the fascinator

Large-brimmed hats blow in the wind, obstruct views and weigh wearers down. Enter the fascinator, a clip or comb-in headpiece that’s usually a bit less fussy — without skimping on style, according to Baltimore designer Ashley Clark.

“The fascinator has been making a huge comeback,” Clark, 35, said. “[It’s] an easy way to have effortless elegance and make a statement, without it being cumbersome.”

Clark opened Soigné Luxury Accessories in Fells Point in 2018. This year, in addition to creating a line of 55 unique couture hats and headpieces for the Triple Crown, she’s working on custom Preakness designs for over a dozen well-known clients, including Ravens players, reality television personalities and movie stars, she said.

“I love when clients go, ‘You have free rein. Nothing’s too crazy,’” Clark said.

Trends at the race will “mimic what’s going on in the high fashion world,” she added, noting the feathered fascinator worn by Florence Pugh at the Met Gala. Clark expects jewel tone hues and non-traditional materials — like metal — to make a statement atop heads at Pimlico.

Dresses with low waists and long hems are in

Some things never go out of style, like waist-accentuating fit and flare dresses, according to Jody Davis, the Baltimore designer who dressed first lady Dawn Moore for Maryland Gov. Wes Moore’s inauguration, and more recently for the couple’s Kentucky Derby appearance.

At Preakness, drop-waist dresses are going to be “pretty powerful, pretty prominent for the season,” Davis said, referencing a cut where the waistline of the dress falls closer to the hips. The skirt could be full and pleated, she said, and hemlines below the knee are proving to be popular.

Davis opened the eponymous Jody Davis Designs in 2010, and creates “comfortable, chic looks,” she said.

For men, comfort — and head-to-toe color — is king

When it comes to outfits for fashion-minded men, monochrome is the way to go this year, according to Baltimore natives Steven White and Dominick Davis, who co-founded Different Regard in 2011 to design, manufacture and style clothing for men and women.

“That boldness of the color really exuberates part of their personality,” Davis, 39, said.

While the traditional men’s getup might include a jacket, collared shirt and trousers, White and Davis are forecasting that brightly-hued leisurewear will have a moment at Pimlico this year. Breathable fabrics made from linen, cotton or bamboo are all smart choices, they said.

“I’m definitely doing pastel this year,” White, 38, said of his own outfit plan. “I’m gonna have loungewear on, I’m gonna have some comfortable shoes.”

Most of what the pair designs at Different Regard, in Mount Vernon, is custom. They’re working with Preakness clients ranging from entrepreneurs to politicians, including Maryland State Sen. Antonio Hayes, who they also dressed last year.

Millennials are bringing the romance

At Brightside Boutique, a women’s clothing store that is a favorite for millennials with locations in Baltimore, Towson and Annapolis, spring is “dress season,” according to Vazquez. There are weddings, homecomings, proms — and Preakness.

This year, in a departure from the fitted dresses of years past, a “romantic, playful vibe” is in, Vazquez, 38, said. Think ruffles, puffy hems, lace, ribbon and bows.

Midi and maxi skirts — with hemlines that hit below the knee (and closer to the ankle) — are a complimentary trend to look out for.

“It’s something that you could wear to Preakness, and you can wear forward, when you’re done with Preakness,” said Vazquez, who opened the first Brightside Boutique store in Federal Hill in 2011.

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As for jewelry, “the bolder the better,” Vazquez said — statement pieces and pops of color are crucial if you’re wearing a subtler dress.

Maryland pride is always in style

Preakness wouldn’t be Preakness without Maryland.

“You see a lot of people really wanting to show off their obsession with the flag,” according to Ali von Paris, 33, the owner of Route One Apparel.

Von Paris started the company while a student at the University of Maryland, with the launch of a lacrosse pinnie commemorating the Thirsty Turtle bar, where she’d worked before its closure. Now, Route One Apparel offers shirts, scarves, hoodies, home decor and tons more — all printed with the Maryland flag or with other Maryland-themed designs.

“We call it flag bragging,” she said of the scene at Preakness. “My goal with our products has always been to bring people together and spark conversation.”

This year, Route One Apparel designed a Preakness shirt depicting a can of Old Bay riding a horse, for a collaboration between Old Bay and Preakness.

Can it get any more Maryland than that?