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BOSTON — It’s 10 a.m. on a Saturday morning and I’m on my hands and knees, crawling across a sea of clothes to reach a Harvard sweatshirt tangled between a striped sweater and pink fleece jacket.

After separating it from the pile, I know I’ve scored and stuff it into my bag. A few feet away I spy a button-down, Gap oxford in perfect condition and that goes in, too.

Not everything is bag-worthy. Mixed in with the finds are shirts with missing buttons or deodorant stains, and other clothes that look a little worse for wear, but at just $2 per pound, they’re worth digging through to unearth the real treasures.

As part of a weekend expedition to explore the second-hand shopping scene in and around Boston, I try The Garment District, a self-described “alternative department store” in Cambridge and possibly one of the coolest places I’ve ever been.

The Garment District, located at 200 Broadway in Cambridge offers shoppers 12,000 square feet of merchandise including vintage clothing, shoes, jewelry, accessories, costumes, along with an eclectic collection of other items like aprons, ponchos, and a stuffed sasquatch head.
The Garment District, located at 200 Broadway in Cambridge offers shoppers 12,000 square feet of merchandise including vintage clothing, shoes, jewelry, accessories, costumes, along with an eclectic collection of other items like aprons, ponchos, and a stuffed sasquatch head.

Opened in 1986 and housed in a former soap factory, The Garment District, located at 200 Broadway, is a venerable, 12,000 square-foot mecca filled with vintage clothing, shoes, jewelry, accessories, costumes, along with an eclectic collection of other items like aprons, ponchos, and a stuffed sasquatch head.

“You can regularly find clothing from the 1950s all the way to contemporary fashion, and every decade in between,” said store manager Amy Gibson. “Sometimes we even get stuff in from the Victorian era and the 1920s. There truly is something here for anyone at almost every price point imaginable as long as you are willing to look around.

Arguably the retailer’s biggest draw is its “by-the-pound” section, which is replenished once a week with six 500-to-800 pound bales of fresh merchandise, unpacked in heaps onto the floor.

“Rain or shine, there is a line of customers outside,” said Gibson, “On especially snowy or cold days, they’re still there, but they’ve developed their own system of leaving their bags in a line out of the door while they await our opening in their cars.”

The Garment District retailer’s biggest draw is its “By-the-Pound” section, which is replenished once a week with six, 500-to-800 pound bales of fresh merchandise, unpacked in heaps onto the floor.

A woman sifting through a pile of clothes next to me confesses that she comes weekly to see what’s new, and that her perseverance has paid dividends in high-end designer finds.

“There are a lot of amazing things people have found in there over the years,” confirmed Gibson. “I have seen people find great fur coats, leather varsity jackets, and designer items from Brooks Brothers, Coach and Burberry.”

While I’m not fortunate enough to bag a pair of Jimmy Choos, or anything remotely close on this trip, I leave with seven pounds of “new” clothes and a vow to return.

Sean Penn And A Boomerang

About a mile away, the Great Eastern Trading Company, a vintage clothing and costume retailer located at 49 River St. in Cambridge’s Central Square District, makes me wish I had a gala, Great Gatsby party or any kind of social life to shop for.

Teeming with gowns, glittery masks, boas and exotic headpieces, it’s a small space filled with a whole lot of sequins, as well as a respectable selection of more traditional vintage items, including flannel shirts and mod graphic tees.

Bobby from Boston, located in the south end of Boston, an area known as the SoWa Art & Design District, is the place to shop for vintage men's clothing.
Bobby from Boston, located in the south end of Boston, an area known as the SoWa Art & Design District, is the place to shop for vintage men’s clothing.

“It ranges from the mundane to the surreal, from the ordinary to the extraordinary,” said Marlene Clauss, who began working for the store in 1973 before eventually taking over as owner in the ’80s. “There are so many sequins and sparkling things, and people like that because they’re not used to seeing that in regular stores. It wakes up parts of their brain that been dulled by malls.”

There is also a decent selection of men’s leather coats in a rainbow of colors, which is what brought Sean Penn and Tim Robbins into the store while filming the movie “Mystic River” in the early 2000s.

“There they were, looking at leather jackets,” Clauss recalled. “I remember Sean Penn being standoffish, but Tim Robbins was a sweetheart.”

Though they didn’t buy the jackets, Clauss said their stylist returned later and made the purchase.

Just a few blocks over, at 552 Massachusetts Ave., is Boomerangs.

Similar to Goodwill, but with a hipper, coffeehouse kind of feel, it’s part of a family of thrift stores owned and operated by the AIDS Action Committee of Massachusetts, with all sale proceeds going to the cause.

It’s the weekend, and the store is crowded with shoppers examining shoes, purses, clothes, books, DVDs and assorted household bric-a-brac, like dishes and candlesticks.

I contemplate buying a decorative tin cow before hitting pay dirt: an unused Trivial Pursuit DVD Pop Culture game.

After waiting in a considerable line of young couples and college students, I complete my purchase and spend a few minutes next door, taking pictures and admiring the images sprayed along Modica Way, a narrow Cambridge street better known as “Graffiti Alley.”

“Graffiti Alley” is a narrow Cambridge street that serves a canvas for free expression where artists can leave their statements in the form of colorful spray painted pictures and messages.

Canopied beneath a colorful, glass ceiling, the alley is a canvas for free expression, where artists can leave their statements in the form of spray-painted pictures and messages. Displayed along the walls are a fair amount of the usual profanities and at least one declaration of support for the Patriots.

Bon Vivant!

Two miles away, Vivant Vintage is a funky, but smart, vintage boutique located at 318 Lincoln St. in Boston’s Allston neighborhood. It’s situated next to a ball bearing center and overlooks the Mass Pike, with a chalkboard sign on the sidewalk that asks: “Aren’t You Curious???”

I admit, I am.

Once inside, the Strawberry Alarm Clock song “Incense and Peppermints” comes to mind, partly because the vibe is so groovy, but more likely because the air is filled with a heady mix of jasmine and patchouli.

“The secret of the smell is that we’re right next door to an incense factory,” said owner Justin Pomerleau. “We couldn’t get rid of the smell if we wanted to. Luckil,y people like it.”

Open just shy of three years, Pomerleau said the purpose of Vivant Vintage is to create an experience that transcends the mundane.

“It allows people to feel safe feeling like themselves,” he said. “We’re trying to represent the uniform of any character, and any character can find their uniform at our store, and feel comfortable expressing themselves.”

All the merchandise is carefully curated, and it shows in the inspired mix of high-quality, vintage items, including assorted men’s boots and Doc Martens, black biker jackets, Jim Morrison-era shirts, kitschy T-shirts from the ’80s, and other cool stuff like school pennants, old cameras, wooden skateboards, a miniature Egyptian sarcophagus, and a lamp made with real deer legs.

“Our customer is really people who are open to trying new things, blending fashion, and not letting themselves be confined to any certain style,” said Pomerleau.

Though I leave empty-handed, it’s only because I’m still debating whether the deer lamp would fit better in the family room or my office.

Is One Ever Enough?

Four miles across town, a red, British phone booth, a la Austin Powers, welcomes visitors outside of Bobby from Boston.

Housed in a converted warehouse and located at 19 Thayer St. in the south end of Boston, an area known as the SoWa Art & Design District, it feels like what you’d get if Ralph Lauren, Humphrey Bogart and your grandpa started a clothing store with some decorating help from Princeton, circa 1945.

Outfitted with rich, dark wood, stacks of old suitcases, worn leather couches and a floor-to-ceiling selection of men’s suits, sweaters, collegiate sweatshirts, wingtip shoes, fedoras, ties, gloves and other accessories, it’s undoubtedly the place I’d shop if I were a man.

Despite lacking a Y chromosome, I still wander around appreciating the aesthetic before heading next door to the SoWa Vintage Market, a permanent flea market with more than 20 vendors, open to the public every Sunday.

Located in the basement of a building filled with artists’ studios, the market draws bargain hunters, antique collectors, and occasionally John Malkovich.

“People like a community and people like a vibe, and I think that’s what we do down in the Vintage Market,” said the market’s co-creator, Stephanie Pernice. “We play our own music, we have our own playlist. People come down the stairs, their heads are bobbing, their bodies are going, they’re having a good time by the time they walk into our space.”

Offering an assortment of oddities (think Raggedy Ann and Andy ceramic wall art) along with more conventional fare like furniture, clothes, acoustic guitars, and fur coats, it’s a cool space for treasure hunting.

A Tom Brady jersey gives me pause, as does a stack of old records. But considering that the last time I owned a record player Rick Springfield still topped the charts, I have to pass.

As far as the jersey goes, there’s already a No. 12 hanging in my closet at home. Then again, you can never have too many.

IF YOU GO: For store hours, visit their websites: The Garment District, garment-district.com; Great Eastern Trading Company, greateasternvintage.com; Boomerangs, aac.org; Vivant Vintage, vivantvintage.com, Bobby From Boston, bobby-from-boston.com; SoWa Vintage Market, sowavintagemarket.com