Boston’s Best Vintage Clothing

January 20, 2011 7:11 PM

One person’s trash can truly be another’s treasure. The perfect addition to your wardrobe may be waiting for you at one of the area’s many vintage clothing shops. Racks of fine fashions, shoes and accessories await the styleish second-hand shopper.
bobbyboston fb Bostons Best Vintage Clothing

Bobby From Boston

19 Thayer Street
Boston, MA 02118
(617) 423-9299

Ladies, if you’ve always dreamed that your man would love shopping, try taking him to Bobby’s. Tweed jackets, vintage Levi’s, seersucker suits, fedoras, bow ties, vests, bomber jackets and much, much more. The fashions from another era abound. There is women’s wear too; it’s just not the store’s specialty. Esquire Magazine actually named Bobby of Boston the best men’s vintage clothing store in the nation.

richgirl Bostons Best Vintage Clothing

Poor Little Rich Girl

374 Somerville Ave
Somerville, MA 02143
(617) 684-0157

121 Hampshire Street
Cambridge, MA 02139
(617) 873-0809

These stores combine carefully curated, current fashions with the best of vintage styling. You’ll find second-hand designer denim alongside pristine pillbox hats. Cocktail dresses, high-end shoes and accessories adorn the shelves. Customers note an impressive array of designer labels “clearly selected with care.” A third location on Newbury Street skips the consignment.


1210 Massachusetts Ave
Cambridge, MA 02138
(617) 491-2654

Restyled in the summer of 2010 under new ownership, Oona’s is filled with fashions of the past that match the styles of today. Dresses, hats, menswear and jewelry galore. The new owner gave the store a boutique-y feel, but held onto the ever-popular costumes. Their famous clientele has included Natalie Portman, Matt Dillon and members of R.E.M.

40south Bostons Best Vintage Clothing

40 South St.

40 South Street
Jamaica Plain, MA 02130
(617) 522-5066

For decades this location was called Gumshoe, and catered to men’s vintage only. Relaunched a couple years ago as 40 South St., female hipsters can now find their favorites as well. Among the fashion finds are cute dresses, carefully broken-in jeans, plenty of plaid, worn leather jackets and some really interesting wool sweaters for both sexes. Open Thursday through Sunday only. Watch for their 50% off sales.

vintage2 Bostons Best Vintage Clothing


22 College Ave
Somerville, MA 02144
(617) 776-3708

Are 50s fashions your thing? Maybe 70s or 80s styles? This small, but carefully curated vintage clothing collection partners in the store with interesting knick knacks, including the owner’s original art creations. Their collection focuses heavily on dresses and accessories. Can’t make it there in person? Check out their Etsy shop online.

Know of a great vintage clothing store we missed? Leave it in the comments below.