Hy’s Toggery

LIVING THE HY LIFE

Clothier unbuttons its collar and evolves

STORY BY HANNAH BURKE PHOTOGRAPHY BY EROICA WAKSTEIN

THE MOST SUCCESSFUL business owners know to embrace change. So, when “business casual” attire began to unravel coat-andtie boardroom dress codes, Hy’s Toggery, originally established in 1969 as a high-end men’s clothier, followed suit.

It’s a pivot that established Hy’s Toggery as one of the top independent providers of casual wear and athleisure in the region.

Walk into their Pier Park shop today, and you’re greeted by a sea of high-performance dress shirts, shorts and shoes that seamlessly transition from office to boat to bar.

But it’s not just an ample stock of the best and biggest brands on the market that keep customers coming back; it’s the combined contributions of three generations of men.

The clothier was established by World War II veteran Hy Wakstein who, until his passing in 2013, reported to his business every day and worked alongside his son, Gary. Today, it’s Gary’s son Josh who handles most of the store’s daily operations and carries on the family tradition.

“I like to joke that I came on board when I was born,” Josh Wakstein said. “I remember helping out back when we just sold suits, ties and hard-soled shoes and had an army of seamstresses in the back making alterations. As a kid, I wanted to wear ‘work clothes’ like Dad and used to hop on my bike in a coat and tie to go play with my friends. I always knew I would join the business.”

During our conversation, I told Josh Wakstein I once had the pleasure of interviewing his father for an article that appeared in Emerald Coast Magazine. Gary, who for most of his life had been accused of sleeping in a tie, corrected me at

Founded by Hy Wakstein, Hy’s Toggery has evolved dramatically over the course of three generations. Hy’s son, Gary, was synonymous with the store when it sold coats and ties from its Panama City Mall location. Gary’s son, Josh, manages today’s Pier Park store, whose shelves are stocked with fashions appropriate to boats and the beach.

the time when I mentioned Hy’s Toggery no longer sold three-piece suits. They do, he insisted — Bermuda shorts, a T-shirt and flip-flops.

“I would say we’re casual, relaxed and ideal for a warm environment,” Josh said. “We carry a lot of performance fabrics that are fantastic for our area’s heat and humidity. When you sweat, the fabrics help you dry faster. And, they’re antimicrobial, so you won’t smell. We carry a big selection from the most popular, high-quality brands so you can find what you’re looking for — and we carry things you didn’t know you were looking for.”

Wakstein said his business’s bestselling labels include Columbia, Huk, Vineyard Vines and Southern Tide. Catering to men and women of all ages, Hy’s Toggery offers dress shirts, T-shirts, maxi dresses, slacks and swimming shorts.

“I quit using my garment bag years ago because nothing needs to be ironed anymore,” Wakstein said. “You don’t even have to hang these things up, they’re so low-maintenance and comfortable.”

Hy’s Toggery also deals in footwear, such as the lightweight and stylish Hey Dude Shoes, which slip on and promise a “sock-like comfort,” and durable, waterfriendly REEF sandals and slides.

While the outfitter enjoys a loyal local clientele, Wakstein said it’s rewarding to help visitors gear up for their vacation.

“Some of our best customers don’t live here,” he said. “We meet folks from all over the country who come in once or twice a year. We’ll catch up on what’s been going on in each other’s lives, and I’ll say, ‘Well, I guess I’ll see you this time next year!’”

Keeping customers satisfied by offering a little Southern hospitality and a premier selection has always been the mission of Hy’s Toggery. And, much like they’re always looking for the freshest styles and top brands, the Waksteins are always keeping an eye out for new ventures and opportunities.

Doing so with family, Wakstein said, “makes every day a joy.”

“People always ask me when my dad is going to retire, and I say, ‘Never,’” laughed Wakstein. “He’s never going to, and I don’t want him to. Retirement is not in the cards for the Wakstein men.”

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