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This Gloucester shop stands the test of time and has a stash of retro clothing and curios. 

For 26 years, vintage shop Bananas has stood on Gloucester’s bustling Main Street. For owner Richard Leonard, however, the journey began even earlier. Leonard celebrated the store’s 39th year in March. Its first location was meant to be an art gallery. Leonard, a Salem art teacher, had wanted a space to display his own paintings for a summer. That same summer, the stars seemed to align—Leonard found his grandmother’s stash of vintage clothing and accessories and added them to his storefront. “I thought people might find them as interesting as I did,” says Leonard. A year later, he gave up the gallery, and Bananas was born.

For Leonard, a lot has changed since 1975. While he didn’t set out to be a vintage expert, it happened. “I learned to tell whether an item is authentic by the fabric or cut of a piece of clothing, or the size and style of a piece of jewelry,” he explains. “I used to research designers and eras in history books. Now, the Internet makes it a lot easier.”

As his store gained notoriety, locals began calling and visiting to ask him to evaluate their own collections, often boxed up in attics or long forgotten. “I like to say that we don’t find items, items find us.” He sees people come in with whole trunks full of their grandmother’s dresses or boxes full of 1940s and 1950s costume jewelry. “I’ll often purchase the whole collection and put it in the store one piece at a time,” he notes. Leonard rotates out merchandise every day to keep the stock interesting for loyal customers. “The ’50s sell better than any other era,” he says. “Although the 1930s are my personal favorite.”

Originally a hardware store, built in the 1900s, the storefront itself is a piece of history. “When we moved in, the ceiling was covered with aluminum,” recalls Leonard. “We checked underneath and found a 1920s tin ceiling that really fit with the personality of the store.”

A collection of vintage lamps, a 1950s television found by the side of the road, and leopard print wall coverings in the dressing rooms round out the store’s funky vibe. “I wanted the store to feel like a small department store, with mini-sections for jewelry, clothes, and housewares,” he says. “We try to appeal to a huge range of customers: locals and visitors, teenagers and eighty-year-olds. People from New York especially seem to love the store—they’re not used to finding authentic vintage that’s also affordable.”

Bananas’s most popular item is, unsurprisingly, emblematic of times past: “People love the collection of clip-on earrings from the ’30s and ’40s, because you can’t find such a wide selection of them in stores nowadays.”

Leonard, a longtime Gloucester resident, recognizes the need for storeowners to grow the local economy. “When I first moved to Main Street 26 years ago, there was a year-long wait for a space. Since the recession, there have been empty store fronts available for years.” To help boost local interest and improve the town, Bananas participated in planning a two-night vintage fashion show benefitting the restoration of Gloucester’s city hall.

“It took us about six months to plan, and 40 people were involved in making the show go off without a hitch,” says Leonard. “We have to be choosy about what events we participate in. I try to choose events that fit our personality as a store, for causes that hit close to home.”