- December 17, 2025
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Penny Gold threw away the first pair of Converse Chuck Taylor All Star sneakers she owned, but she’s spent the rest of her life making up for it. Seven hundred and thirty three pairs later, she may own more Converse shoes than anyone else in the world. Just to be sure, she applied for a Guinness World Record on Jan. 5. She needed to rent a U-Haul truck to drive her shoes to the counting ceremony.
“Hi everybody, welcome to my shoes!” she yelled toward a train of first-graders winding their way into the multi-purpose room of Maitland’s Jewish Academy of Orlando at about 10 a.m. Overflowing from the tops of more than 20 tables, a kaleidoscopic parade of Chuck Taylors perched a few feet off the floor. They’re used to this lazy existence by now. Each one of them waits an average of two years to take a walk.
Gold, ever smiling, has worn almost all of them at least once. The morning of the official count, bursting with energy and sporting an outfit that made more noise than even her voice, Gold wore a pair of shimmering size nine Chuck Taylor high tops the color of her name. They might as well have her name on them; for the better part of the last two decades teaching at the Jewish Academy, she could be recognized by anybody staring at the floor.
But not on Jan. 5. As she paced the room, stopped every few feet by friends and gawkers who wanted to ask her which is her favorite pair, she passed by more than a few well-worn Converse on the feet of family, students, fellow teachers and random strangers. In Gold’s world, Converse fever is contagious.
In unlaced gray low tops, her son Lander was the one who called the Guinness Book of World Records. Their instructions: shoot photos of every pair, catalog them and do a public counting with seven witnesses, or pay up to $10,000 to have a Guinness official do the same. The choice was easy. Plenty of family and friends were ready to help. So on that cold morning after the holiday break, they trucked in more than 30 crates of shoes that had taken a month to inventory, and they started quantifying Gold’s obsession.
Across the room, Jewish Academy Principal Lynne Shefsky, shod in a pair of borrowed black All Stars covered in colored rings, talked to a reporter about the reach of Gold’s passion for a very particular type of shoes.
“In the third grade, the kids had to wear Converse sneakers,” Shefsky said. “They knew it before they started.”
Gold taught the third grade here while she traded curiosity for addiction. In the first 25 years of collecting, she may have picked up a few dozen pairs. In the last 15 years, it’s been in the hundreds.
Pretty soon after her collection edged beyond a pair for every day of the year, the kids started making a game of trying to catch her wearing the same pair twice. They kept journals and videos, hoping for the one day that their teacher would finally slip up. It never happened.
That’s not hard to believe considering how often she picks up a new pair. She strolls into the Orlando area’s three Converse outlets once a week. She rarely leaves without new shoes.
“Sometimes it’s only one pair,” Gold said. “But it’s usually more.”
Her husband, Barry, had to remodel their closet to fit the shoes, but he’s gotten used to the growing behemoth behind the closet door.
“My clothes have to go in another room,” he said. “But we’ve been married 40 years. This is nothing.”
Finding the impetus to this madness takes a journey farther than Gold’s feet could carry her, all the way back to her childhood roaming the sidewalks of New York City. Every time she steps into a pair of Converse, she takes a step back in time to a hometown far away that gave birth to her accent and her passion. She laces up a pair, and all the sudden she’s home again.
“They always reminded me of being a kid in Brooklyn,” she said. Back then her favorite shoes only came in red, yellow, black or, her first pair, white low tops. She outgrew those, but never outgrew her love for her favorite footwear.
Everyone at the school knows about it by now. She’s the Converse Lady. If anybody wants to buy her a gift, the choice is obvious. About 14 years ago Jill Braunstein, whose son Michael was in Gold’s class, bought a pair of hi-tops and spent hours sewing buttons and baubles on with fishing line and lacing the pair up with tie-dyed ribbons, hoping to make Gold’s Hanukkah a special one.
“I was overwhelmed,” Gold said. “I was jumping up and down, gave him a big hug.”
But most of the shoes she’s bought on her own, which begs an obvious question that 7-year-old Benjamin Shapiro couldn’t help but ask: “How do you have all this money for all these shoes?”
It turns out she doesn’t. Shopping for deals at the local outlets, she buys them for less than $25 each most of the time. They’re always different. She wants a new pair every time. For a while it was pairs that were an homage to AC/DC, Metallica or other famous rockers. She owns a pair made from see-through plastic. Another pair has eggs, sunny side up, adorning the ankles.
But ask her what her favorite is, and that’s an easy guess. She strolls toward a pile of shoes at the front of the room to grab a pair of black hi-tops that read like a subway map. Just about where the old BMT subway line meets her left big toe is Lorimer Street station, where the train used to carry her home. Decades later, her shoes still do, every day, though the location has changed a bit.
With the official count finished, she was all smiles as she greeted more visitors. A sign on a post in the middle of the room read “Conversalations, Penny”, seemingly to pronounce some sort of finality to Gold’s quest. But will she ever stop? Never, she said.
“Especially with my friends feeding the habit,” Gold said. “I hope to get to 1,000, but I know I’ll go over.”
Lucky for her, the Converse stores are always within shopping distance in Orlando. On Saturday she made her usual rounds, hoping to find something she’s never seen before. They’re usually waiting there for her, handpicked by Converse store employees.
But before she could make it there, the employees had already brought her a gift: a pair of white hi-tops colored with a rainbow of signatures, congratulations and thank yous. Make that 734 pairs.