As any real Upper West Sider can tell you, Tip Top Shoes is a neighborhood institution—as dependable and iconic as nearby Zabar’s and Barney Greengrass, and with product just as fresh and tempting. While countless retailers around it have come and gone, Tip Top has remained a fixture on West 72nd Street decade after decade. Generations have grown up shopping at the store, which turns 85 this year. They’ve passed the tradition along to their children and their grandchildren. They might even have rubbed shoulders with famous Tip Top shoppers like John Lennon, James Gandolfini, Carolyn Kennedy, or a young Marc Jacobs. Or they might have discovered one of the many now-famous brands the retailer helped introduce to American shoppers, from Birkenstock (Tip Top was the German company’s first North American account) to Mephisto, Timberland, Ugg, and Ecco. Late owner Danny Wasserman’s gift for finding the next hot brand in footwear was legendary.
Now stepping into Danny’s role are his children, sibling co-owners Lester and Margot Wasserman, the third generation to run the family business. (The original owners opened the store in 1940 and sold it to Danny’s dad, Max Wasserman, in 1964. Max officially passed it along to Danny in 1980.) Lester and Margot took over after their father passed away last fall, but they’re hardly newbies. They grew up in the store, and the biz is in their blood.
“There’s not one inch of this building that I don’t know. This is my home,” says Lester. “To be a part of this piece of the fabric of New York and the global footwear community is pretty amazing.” Adds Margot, “I was always proud to work at Tip Top, but hearing stories from people in the industry about my dad’s legacy makes me even more proud to do what I do every day.”
Defying the Odds
In the age of consolidation and ecommerce, how does an old-school, independent sit-and-fit retailer not just survive but thrive? The secret is in the service, selection, and spirit of the team.
“We’re selling a lasting relationship that starts with a friendly face, a smile, a greeting at the door from full-time career salespeople,” says Lester. You’ll never walk into Tip Top and find employees with their heads down, scrolling through their phones. “We’re looking at you, we’re greeting, we’re seating. We’re able to build sales just by chit chat.” It’s the “lost art” of great salesmanship in action—the kind of approach that fosters real trust and ensures that the customer walks out happy, says Lester. “That’s a highly underrated skill in the modern world,” he adds.
Brand Director Adir Landes, a relative newcomer with just under five years’ tenure at Tip Top, likens the store to the eponymous Boston bar from 1980s sitcom Cheers. Even if everybody doesn’t literally know your name here, they make you feel welcome. “I grew up in the neighborhood, and Tip Top was always a beacon to footwear,” he says. “This was the number one place I wanted to work.”
Of course there’s more to Tip Top’s success than congeniality. Beneath the gregarious vibe is deep expertise. Many staff members have been with the store for decades. “The employees on the floor, behind the scenes, and in management are like family to us,” says Lester. “They’ve been with us longer than my children have been on this earth. I grew up with them. They taught me how to sell shoes.”
Solid business sense, strong relationships with vendors, smart restocking strategies, a sixth sense for what will sell, and a stellar selection are equally key to success at Tip Top as well as its two sister stores, both located in the same block of West 72nd Street—Tip Top Kids, opened in 1987 and now one of the last dedicated children’s shoe stores in Manhattan, and West NYC, which started as a sneaker wall at Tip Top and evolved into a standalone boutique with limited-edition sneakers, streetwear, and hats in 2007. (See sidebar, p. 20.)
“We like to say if we don’t have it, you probably don’t need it,” says Adir of the selection at the three stores. “We’ve got shoes for literally every occasion, from this week’s Jordan drop at West to the most comfortable shoes for your grandma at Tip Top.”
What’s more, “We pride ourselves on measuring feet, especially in the kids’ store,” says Margot. “We really take the time to get everyone the proper fit, which is unique in this day and age.”
That’s a crucial point of difference in an era where “shoes are available just about anywhere,” says Lester. “You can buy shoes on your iPhone at 3 in the morning, but folks want to come to Tip Top for the nostalgic, old-school play that involves a shoehorn, a fitting stool, a Brannock Device, [and the ability to] touch and feel the products.”
Although Tip Top’s core shopper is 45-plus and female (the selection skews 70 percent women’s), “our customer base is diverse,” says Lester. That’s why “we carry so many brands. We’re always asking how new product—from mundane to eccentric—could have a space in one of our doors.”
From mundane to eccentric. Upper West Siders themselves have been described in similar terms. Labeled everything from bohemians to curmudgeons, they’re a notoriously eclectic bunch, but Tip Top wouldn’t have it any other way. “Upper West Siders are some of the best, most entertaining customers out there,” Lester says. “When you sit face to face at the stool with some of these people, you learn plenty. There are laughs and great stories shared. It’s quite an experience.”
Most shoppers come in with “a good sense of style and an idea of what they’re looking for, but they trust us to find the best, most comfortable version of it for them,” Lester explains.
Evolving with the Times
Through the decades, Tip Top has weathered its share of challenges, from the blackout of 1977 to the dark days following 9/11 to the Covid pandemic to the most formidable challenge to date—the shift to online shopping.
“Online you win when you have the right size and nobody else does, or when the analytics favor you. That’s all great stuff, and it’s part of the jigsaw puzzle, but our brick-and-mortar stores win with human interaction,” Lester says. If the advent of ecommerce has a silver lining, it’s that “Our customer service game got even better,” he says. “Each customer got more important. The best customer is always the one in front of you.”
To keep up with a changing shopping paradigm, Tip Top’s own ecommerce business has grown, too. (Their website now offers same-day delivery Monday through Friday for online orders placed before 1 p.m.) So has the retailer’s social media presence. Tip Top Shoes, Tip Top Kids, and West NYC have a presence on Instagram and Facebook, with a unique voice and style curated for each platform and store. “Everything’s got to be treated with respect and created for its own platform,” Adir explains.
The team learned through trial and error that “Shoes styled well on a nice colored background don’t necessarily move the needle,” Lester says. For the flagship’s socials, “Adir had an idea to take a more behind-the-scenes look at a shoe store, where we’re doing things like a day in the life at Tip Top Shoes. You see real people in a real store that looks like a lot of fun.”
“We have a different strategy at West,” Adir adds. “There, we like to do more viral stunt videos for product launches. For example, we did a project with Adidas that dropped in December at West. One of our videos got 1.3 million views—far more plays than that week’s Jordan launch even though we have about 50,000 followers and they’re in the 20 million range.”
Tip Top Shoes also made its first foray into local TV ads in spring 2024. “We use voiceover [talent] with a very thick New York accent. It gives the commercials a very upbeat, fun, New York kind of feel,” says Adir. “We’ve seen a great response to that.”
The commercials, which sometimes promote the store and sometimes promote specific brands it carries, were a longtime dream for Lester, who holds a special place in his heart for the iconic local commercials he grew up with, like Roscoe the Bedbug Dog from Bell Environmental Services. In New York, “Everyone knows Roscoe. Everyone should know Tip Top Shoes,” he says. “You have to let people know you exist.” To that end, increased TV advertising is one of his top goals for 2025.
Tip Top’s delivery system for self-promotion has changed over the years, from promoting Birkenstock as “the ugly shoe that makes you smile” in Rolling Stone and The Village Voice in the 1960s, to running onscreen ads in local movie theaters, to taking out regular space in The New York Times, the erstwhile gold standard for retail advertising, in Lester’s opinion. More recently Google ads have been a “tremendous success,” but with shortcomings: It’s hard to know what sold and who bought, and it’s even harder to convey personality through a Google ad, he says.
This year naturally calls for more fanfare. Tip Top plans to celebrate its big birthday through special events and collabs with brands including Kizik, Clarks, and Adidas. (See sidebar below.) The store will also ring in the fall with a Birkenstock Oktoberfest event featuring a live band, bratwurst, cider, beer, and pretzels to pay tribute to the brand’s heritage and the Wasserman family’s roots. “Danny spoke fluent German, and the Upper West Side used to be full of German Jews, so we feel it’s fitting to serve German fare that day,” says Lester.
Carrying on a Tradition
Though losing their dad was a tremendous blow, Margot and Lester feel well-equipped to take up the mantle. Both siblings spent years watching Danny at work and learning from the master. “To have him as my teacher and mentor was the honor of a lifetime. I’d like to think he’s still keeping a watchful eye over what we’re doing,” says Lester. “We’re not trying to shake things up too much. We’re standing on the shoulders of those who came before us, and that’s been a very effective technique. Things are still moving in the right direction. We had a great 2024…and we’re still very bullish on 2025.”
Since the Covid pandemic, Tip Top’s fastest-growing segment has been athletic. The barefoot trend is on the uptick too, with Vibram FiveFingers and Lems selling well. Slippers continue to be popular too, like Ugg and Haflinger. Still, the daily quest to find the next hot style continues. “We’re always asking, ‘What’s the next lightning in a bottle?’” says Lester.
Though brother and sister have contrasting work styles, they complement each other. “I’m very organized,” says Margot, who spent eight years working for Ralph Lauren before joining the family business in 2012. “You can ask me for an email from 2004, and it’s filed away. I keep everybody rolling, make all the appointments for the shoe shows, keep all my orders together, and never mess up a style number.”
Lester is the opposite. “Our dad would sometimes write purchase orders down on napkins. If you ever saw his office, it looked like the FBI had flipped it. I definitely took that from him,” he says. “My strong suit is dealing with people. I’m able to take a bad situation and turn it upside down and get a laugh and a good Google review out of a customer.”
The latest generation of Wassermans say they’re proud to be writing a new chapter in Tip Top’s ongoing story. “It wasn’t always a bowl of cherries, but part of the sweetness is that we weathered the storms,” Lester says. “We were there for the ups and downs, and somehow we managed to persevere, come out on top, and find the next hot products. Being a part of that time-honored legacy is truly an unbelievable honor.”
Collector’s Editions
To mark Tip Top’s 85th anniversary, the retailer is partnering with Adidas on two special commemorative shoes—a Men’s SL 72 RS and a Women’s Handball Spezial.
The men’s sneaker (retail $120) pays tribute to Tip Top’s sit-and-fit brown shoe heritage with perforations evocative of wingtip oxfords on a rich chocolate suede and nylon upper with a leather tongue. Printed on the insole is the phrase “Your feet are in good hands,” Tip Top’s tagline. In each box is a postcard with a painting of long-time owner Danny Wasserman, who passed away last fall.
The women’s sneaker (retail $130) is multi-color bouclé, a nod to women’s power suits of past eras, and is adorned with the phrase “West Side Best Side” on the heel tabs. “The women’s shoe is a little more fashion-forward, a little more vibrant and colorful, whereas the men’s is more of a nod to Tip Top’s history. It isn’t brown, but it gives that heritage authentic vintage look. We’re super excited about both of them,” says Brand Director Adir Landes. “I’ve never seen another brown shoe retailer have a sneaker launched strictly to themselves.
Both shoes launched at the end of April in store and online at West NYC and Tip Top Shoes. A portion of the proceeds will be donated to Two Ten Foundation.
Look for a Clarks Wallabee collaboration toward the end of 2025. —K.P.
