The inspiration for this article came, as it often does, from spotting someone at work wearing practical yet fashionable shoes, prompting me to look them up later. This time, it was a host at Philadelphia’s Bok Bar, a popular seasonal rooftop venue with open-air service. The shoes in question appeared to be stylish Keens—a sporty sandal that offers toe protection, solid support, and the perfect balance of breathability for summer.
These shoes are crafted for long hours of walking and standing in all kinds of weather—whether you're working a double shift at the bar or grabbing a seat for yourself. Reflecting on the Keens and the variety of tasks involved in outdoor events, I thought about the farmers market vendors, small business owners, and event organizers who work in the open air. I wanted to hear their recommendations for shoes that provide both support and durability while remaining lightweight enough for warmer weather. So, I asked around.
“I recommend shoes that are comfortable, waterproof (or at least water-resistant), and offer toe protection in case something heavy falls,” says Holly Collins, the owner of Universal Energy Healing, an herbal products booth at the Marblehead Farmers Market in Marblehead, Massachusetts.
“For me, it really depends on the season,” said Matt Saperstone, the owner of Nilla Coffee, a specialty coffee roaster in Philadelphia, when speaking to HuffPost. “Comfort is essential, especially when you're standing in one spot (or shifting slightly) for hours.”
Saperstone also mentioned that with his frequent market visits, he doesn’t often think about his shoes. To me, this was the ultimate endorsement: supportive summer footwear that's so comfortable and easy to wear, you can simply slip them on without a second thought.
1. New Balance walking shoes
In the warmer months, Matt Saperstone, owner of Nilla Coffee, which sells at the Schuylkill River Park Farmers Market and other locations around Philadelphia, opts for walking shoes from New Balance. "They help me handle all the back-and-forth movements and loading/unloading of the vehicle," he said. While he didn’t specify a particular model, the New Balance FuelCell Walker Elite sneakers are known for their responsive cushioning and supportive outsoles, perfect for walking and standing. Available in six colors for men (sizes 5-16) and five for women (sizes 5-12).
2. Keen Newport sandals
These are the very Keens I spotted at the outdoor bar. The brand is also favored by Nancy Chapel, the owner-operator of Alpaca Country Estates in Terrebonne, Oregon, and a new vendor at Portland Farmers Market in Oregon. "I wear Keens, they’re my number one choice," Chapel shared. Known for their durability and outdoor performance, Keen’s Newport sandals provide toe protection and ample arch support for all your outdoor activities. They dry quickly, are machine-washable, and feature a fabric lining that prevents blisters. Available in a variety of colors, in men's sizes 7–17 and women's sizes 5–11.
3. Anything from Merrell
4. Blundstone Chelsea Boots
5. Hoka trail running shoes
Hoka
"If it's particularly hot or it's an event where I'll be getting a lot of steps in, I go for my Hoka trail running shoes," says Drucker.
Made for the trail but equally as supportive in the city, Hoka's Challenger 7 is made with a breathable mesh upper and soft foam. It offers a rubber outsole inspired by gravel tires to keep you steady as you move. These come in a bunch of colors in men's sizes 7–15 and women's sizes 5–12.
Get them in men's sizes from Hoka for $145 and in women's sizes from Zappos for $144.95.
6.
Toms Women Kameron slip ons
Toms
Holly Collins, owner of Universal Energy Healing, an herbal products vendor at the Marblehead Farmers Market, wants something with arch support and a little style. "Being a newbie to the farmers market scene, I am finding the Tom’s Kameron Green slip-on to be supportive and functional for standing with the Ortholite supportive soul," she said.
A modern take on the classic Toms shoes, these slip-on sneakers have a supportive rubber outside and a supportive insole. These come in eight colors in women's sizes 5–12.
Get them from Toms for $38.99+ (originally $59.95).
7.
Dr. Martens Audrick Chelsea boots
Zappos
"I wear Doc Martens Audrick Nappa leather platform Chelsea boots to every event," MaryJo Callaghan, founder of flower farm and gardening service Blume Vermont, told HuffPost. "I also wear them gardening and working in the field."
A super wearable statement shoe, these Chelsea boots have elastic gore panels with grooved heels and the brand's timeless yellow stitching. The air-cushioned rubber outsole is oil-, fat-, acid-, petrol- and alkaline-resistant with extra slip and abrasion resistance for stability. These come in women's sizes 5–12.
Get them from Zappos for $169.95 (originally $200).
8.
Danner Cascade boot
9.
Fila Disruptor II's
10. Classic Crocs
11. Crocs work shoes
"I wear the Crocs work shoes and swear by them," says Lilly Tapper, owner of Three Hundred Fifty bakery, which sells products at the Marblehead Farmers Market in Marblehead, Massachusetts. These shoes, known as the 'caffeinated' version of the classic Croc, feature slip-resistant treads and an enclosed toe and heel for added support and safety. Available in black, they come in men's sizes 4–13 and women's sizes 6–12.
12. Allbirds tree runners
Ian Kingsbery, the general manager of the popular rooftop Bok Bar in Philadelphia, notes that many on his staff wear Allbirds. "They're super light and breathable," he said. Jesse Janelle, owner of Special Pup vegan dog bakery at the Marblehead and Salem Farmers Markets in Massachusetts, also swears by these knit shoes. "My husband and I both wear Allbirds for markets — no pain, and it feels like having on slippers all day." Made from eucalyptus tree fiber, Allbirds are machine-washable and breathable. Available in various colors, they come in men's sizes 8–14 and women's sizes 5–11.
13. A pair of good supportive Birkenstocks
"We love to wear Birkenstock brand shoes. They are the most comfortable and stylish shoe," says a representative from Down North Pizza, a mission-driven pizza shop based in Philadelphia that is currently running an outdoor pop-up at Bok Bar. Known for their contoured footbed and excellent sole support, Birkenstocks are a favorite among chefs and street stylists alike. The brand's super-grippy clogs come with an adjustable backstrap and high-traction sole, available in black and white in men's sizes 6–15.5 and women's sizes 4–12.5.
14. On Clouds
"We wear On Cloud running shoes when we are at the market," says Liv Dolce, owner of Liv Granola at the Marblehead Farmers Market. "They're the most comfortable and supportive shoes, and the easiest to slide on and off. I wore them even when I began Liv Gourmet Granola, baking all of our granola in a local church kitchen." Made with elastic laces, these running shoes have a slip-on design and a shock-absorbing sole. The zero-gravity foam sole evenly distributes your weight, making each step feel light and buoyant. Available in various colors, they come in men's sizes 7–14.
15. Skechers Slip-ins
16. Superfeet insoles
Buzz
