Dorling Kindersley Ltd / Alamy
Samantha DiMauro
August 07, 2014

The best of my wardrobe was purchased from the racks of Boston’s vintage stores. It’s where I go to look for striking, standalone pieces to pair with workday basics, though I usually can’t help but walk away with a few show-stopping lucky buys as well. When shopping the best collections on the city’s resale scene, be prepared for a successful treasure hunt when you least expect it. I’ve skipped away with incredibly affordable finds, including a glamorous, 1950s wool trench dress coat made in Uruguay that fit me so unexpectedly well I simply had to buy it on the spot, even if it was the peak of August! Each store seems like a secret, and the unique items you’ll walk away with are often conversation starters. For the brave hearted, pay-by-the-pound piles can offer a surplus of rewards, while on Boston’s main drags, an endless array of secondhand shops resell only the most sought after designers and high-quality goods.

Oona’s Experienced Clothing

Founded in 1972, this is the most rewarding store for true designer vintage wear in the Boston area. The owner returns from weeklong international excursions with rare finds to add to the ever-changing stock of effortlessly chic and glamorous clothes, shoes, and accessories. Find the entrance a little way off Harvard Square in the corner of a picturesque, brick courtyard, complete with vibrant wall mural and an ivy-covered facade.

Bobby from Boston

Step back in time when browsing this archive for quality, vintage men’s attire. Mixed among timeless antiques you’ll find a rather dapper selection of sports coats, silk ties, vintage Levis, and gently worn leather shoes from the 1920s–1980s. The store easily blends in with the art galleries on Thayer Street, so look for the bright red British telephone box near the entrance.

The Garment District

The vintage department at this thrifty hipster heaven boasts boundless racks of real retro wear arranged by the decade ranging from the 1950s through the 1990s. If you’re feeling fearless, go here to sift through he heaping Dollar-a-Pound stockpile of secondhand clothing. With some practiced patience and a thorough digging, you can walk away with some incredible one-of-a-kind finds.

Rick Walker’s

Tucked amid the high-end designer clothing boutiques, this specialty store has been selling edgey style out of a basement on Newbury Street since 1932. We’re talking glitzy belt buckles and cowboy hats, vintage Western shirts and Wranglers, and funky costume jewelry. Go here for the incredible collection of unique and multi-colored leather cowboy boots, arranged on shelves and bookcases framed with vintage license plates and photographs.

The Raspberry Beret

This trendy, local consignment store is the place to go for quality-assured complementary gear like handbags, scarves, belts, and jewelry. In summer, vintage rompers and sun dresses in retro prints hit the racks, and on a warm day you’ll find further reduced-price wears for sale on the sidewalk. The Cambridge outpost caters to the neighborhood’s bohemian, creative woman, and carries labels such as French Connection and Escada. 

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