
Pirate-themed parties? Ring dip challenges? Sneaker collabs with a local twist? They’re hardly run-of-the-mill retail experiences. But then Fleming’s Comfort Footwear is no run-of-the-mill footwear store. The second-generation-family-owned Tulsa business, which turns 40 this year, has written its own success story by balancing a spirit of zany fun with a continually updated selection of high-quality comfort product and friendly, sit-and-fit service from knowledgeable shoe dogs who love their work and their customers.
Much of the store’s unique and often quirky approach stems from its owner’s creative mindset. Ryan Fleming, son of the shop’s founder, has been known to dress up as Footie the Elf for kooky holiday social media posts. He also draws from his background as a musician to write shoe-themed jingles and tribute songs that he posts on his store’s Facebook and Instagram. (“My Mephisto” to the tune of ’80s pop-rock band The Knack’s “My Sharona” is one example.) He’s locally famous for hosting in-store extravaganzas like a Star Wars–themed May the 4th event with Ara. Sam Spears, president of Ara North America, attended in a Darth Vadar costume, while Fleming dressed as Obi Wan Shoe-nobi.
“People look forward to the crazy events where we partner with brands. Those are our biggest days of the year,” says Fleming, who also teamed up with Ara on a pirate day, melding the brand’s name with the buccaneer catchphrase “arrrr.”
“Customers put the dates on their calendar and come in to take pictures with us. Some of them dress up for the occasion,” Fleming says. Newcomers stop in to find out what’s going on. “If you walk into a store for the first time and find people dressed like pirates on a random day, it’s hilarious,” Fleming says. “It’s a party.”
The concepts aren’t always corny. Case in point: Fleming’s hit big with a one-of-a-kind Psudo sneaker last year. “Psudo mentioned they were doing custom prints, so I asked if they could do a Tulsa flag. [Brand founder] Michael Rich gave me a draft in five days, and in six weeks I had a prototype. He flew out for our launch party, so when people came in to try on the shoes, they could meet the owner of the company.
“People went nuts for that shoe, especially when they found out Psudo made it just for our small, humble, mom-and-pop store,” Fleming says. “Customers sent me pictures from the Olympics with the Eiffel Tower in the background and everywhere else they’d worn their flag shoes. I sent the pictures to Michael to show him that his custom shoes were all over the world.”
Not only do Fleming’s customers praise the shop as a “Tulsa treasure” and “the stuff dreams are made of” on social media, but vendors are equally complimentary.
Spears, who has been familiar with the retailer since his university days in Tulsa in the ’80s, calls Fleming’s “an amazing single-door owner-operator that punches way above their weight class.” He adds, “They set themselves apart from the pack with a very curated selection of all quite premium brands that are not necessarily typical for a comfort footwear store. Ryan doesn’t take himself too seriously, but he takes business extremely seriously. And he thinks way outside the box. He’s a real renaissance man.”
Ari Levy, national sales manager for Naot, agrees. “Ryan’s very creative, and he truly has a passion for what he does. Both his vendors and his customers can see this. He fosters a connection with both,” says Levy. “And he does some great social media posts. My favorites are when he plays his guitar.”
Mephisto USA CEO Rusty Hall is also a fan of Fleming’s sometimes wacky social media marketing. “Ryan is an uninhibited entrepreneur who will use any means possible to bring energy to his store,” Hall says. “He’s funny, yet very smart in his dealing with his customer base.
“The market is tired of boring malls and department stores with zero service,” Hall adds. “Retail started as—and continues to be—one of the best places to look for entertainment, and Ryan brings that into his specialty shoe store.”

Heart and Sole
Fleming’s offers plenty of substance to underpin its flashy events and collabs. The store’s winning formula involves deep expertise, dedication to making customers feel cared for, and a quest to continually refresh the merchandise mix.
“I’m always looking for quirky, expressive, unique items that catch the eye, combined with basic functional things,” Fleming explains. His customer base leans female (65 percent) and tends to be middle-aged or older. Some have challenges like plantar fasciitis, diabetes, or difficult feet to fit and want help finding footwear to prevent pain and help maintain their health.
But that doesn’t mean they’ll settle for boring or basic styles. “The community in Tulsa enjoys a combination of fashion-forward footwear and pragmatic selections,” Fleming explains. “People like bold colors, so sometimes a red sneaker will outsell a black one. Or a multi-colored sandal with primary colors will be my number one seller.”
He likens curating a great selection for his shelves to developing a great menu for an ice cream shop. “You’ve got to have chocolate and vanilla all the time, but you also need to have experimental stuff like lavender chocolate chip with macadamia nuts. Sometimes it goes over really well,” Fleming says. “If we go out, we’re going out in flames because we tried wild things. You’ve got to go for it because that’s also what brings about success.”

Here Comes the Son
You could say Fleming’s defied expectations from day one. Ryan’s dad, the late John Fleming, founded the business in 1985, against the advice of virtually everyone he knew. John was an oil man, but the bottom dropped out of the industry in the 1980s. Friends urged him to bide his time until it rebounded or to move away, but he loved Tulsa and wanted to raise his family there, so he opened an eponymous full-service comfort footwear shop.
“People told him it was a terrible idea,” says Fleming, who grew up in the business along with his two younger brothers. “You could say I’ve been doing this my whole life. I recently found a photo of me in the store when my dad was doing the buildout. I was three and a half years old.”
Fleming considers it “kind of bonkers” that, at 43, he is married with his own three- and five-year-old children and running the store himself. His wife, Carla, pitches in with payroll and accounts payable.
“They are truly a family footwear store,” says Spears. “Carla and the children are frequently in the store, especially on a Saturday before or after a soccer game, to check on Dad, bring homemade snacks for the staff and customers, get a pre-game pep talk from Dad, or give him a play-by-play of the game.”
Fleming considers it an honor to carry on the tradition his parents built of “providing the community with an old school, one-on-one shoe consulting environment that people look forward to visiting and spreading the word about,” as he puts it.
That tradition was founded on a customer-first approach. In the early days, “my dad brought in two old shoe dogs who had been selling footwear their whole lives and were about to retire. They taught him the basics of how to greet people, measure feet, properly fit, problem solve, maintain the customer book, call top customers, and deal with returns,” says Fleming. He learned the fundamentals of successful retailing from his parents and passed his knowledge along to his team. “We’re all shoe dogs,” he says. His “rookie” employee has been with him for six years; his oldest hire has been at the store for 19 years. “There’s a lot of knowledge here, and that gives people confidence. It builds trust.”

The Fleming’s team never lets their enthusiasm for a product bubble over into a high-pressure sales approach. In fact, the store puts a premium on treating customers with “compassion,” in Fleming’s words. “We want to be a place where all people feel welcome when they walk in the door, leave feeling cared for, and want to come back.
“We’re not going to jump all over customers and hound them,” he adds. “We’re not in this to make a sale and be done. We’re solution minded. We constantly brainstorm ways to modify shoes to accommodate foot ailments to help our customers. If there’s a problem, we figure out how to fix it or deal with a return properly, so people talk to everyone in their neighborhood about us. Long-term focus is always the name of the game.”
“Ryan’s passion to serve is always evident on the sales floor with his customers. He can turn the most challenging situation around with his charm, quick wit, and exceptional foot care expertise,” says Spears. “He genuinely wants to help people and make someone’s day a little bit better.”
Cultivating a warm, welcoming vibe starts with ensuring that the sales team is happy. “I tell my people there’s no ceiling here. We pay really well, we give our people growth opportunities, and we openly share knowledge,” says Fleming. “Some stores and salespeople want to keep their knowledge in a vault like it’s top secret. They don’t want to tell anyone what they know because they’re afraid it will give someone else an edge. I share everything I know with my salespeople, my customers, and other retailers. People come back to you when you’re generous with knowledge.”
True to character, Fleming bakes fun into the workday for his team. “I’m involved with a men’s workout collective (F3), and I have a pull-up bar and ring dips in the back. If we’re having a hard time or we’ve had a challenging customer, we’ll do some pull-ups to get the blood pumping, then start fresh,” he says. “That’s our version of retail therapy.
“Our motto is ‘It’s a good day to crush it.’ If we have a challenging day, we go home, go to sleep, then wake up and say, ‘Today’s a good day to crush it.’ If you believe you have what it takes to make it happen, you can make it happen.”

Ramblin’ Plan
In truth, Fleming didn’t expect to find himself running his parents’ store. After graduating with a business degree and a studio art minor, he took a job with Karavel Shoes in Austin, TX, where he helped build their outdoor and athletic division from 2004 to 2007. He was recruited by Paul Evans of Kanner Corp and spent two years as a sales rep for Kanner but left in 2009 to travel around the world, volunteering and soul searching.
From 2011 to 2013, he was working as a missionary in the Himalayas, helping to sell handcrafted goods made by people with disabilities, when his mom, Angela, decided to sell the family store. “I said I would come home and give running it a whirl,” Fleming recalls. Retail proved a good fit and eventually he bought the business from her.
“Why do I do this? I love working with people,” Fleming says. “I love when people leave our store feeling better than when they showed up. Sometimes they have a hard day, and they come shop with us because they know we’ll encourage them. There is no greater compliment than hearing someone say, ‘I just wanted to come by.’ If we make people feel better, that’s awesome.”
Of course, no retail business is without challenges. Hurdles range from helping younger customers who’ve never had their feet measured feel comfortable sitting down face-to-face with someone on a fitting stool, to dealing with vendors who attempt to snatch business from Fleming’s after the store helped them build a customer base.
“Partnerships matter to us,” Fleming says. “Some brands have good product, but if I don’t feel supported, I search for other options. When my customers ask what I think about a brand, I’ll tell them honestly that we have a better relationship with someone else. All our top sellers come from companies that value small independent retailers.” Among those top sellers are Ara, Brooks, Finn Comfort, Foot Balance, Mephisto, and Naot.
The soft fall season of 2024 presented another challenge, but Fleming applied a lesson he learned as a sales rep. “The stores that close are the ones that offer no excitement. You have to try something fresh no matter what,” he says. “I bought big for 2025 to make sure every time someone comes in, they see new product they’ve never seen before.”
Another goal he’s set for 2025 is to network with local doctors, podiatrists, chiropractors, gym staff, and others who deal with people suffering from foot pain to explain how Fleming’s knowledgeable staff and custom inserts might help their patients and clients. “I want to bring examples of shoes in to show them what we offer,” he says. “Nothing beats a handshake and people asking you questions in person.”
“Fleming’s is one of those stores that you just can’t help but cheer for,” says Spears. “And a big reason for that is Ryan. He’s a guy who genuinely only wants to help people, provide for his family and staff, and make someone’s day just a little bit better.”