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Best Places to Shop in Boston

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Posh department stores and malls lie alongside thriving, one-of-a-kind independent stores in fabulous, one-of-a-kind Boston. And here’s a nice perk for your wallet that couldn’t be a better intro to a Boston shopping guide: Massachusetts charges no sales tax on clothing purchases up to $175. The effects of the Tea Party continue to this day.

Boston Shopping Guide

Head to Newbury Street

If you can handle the in scenes in Miami, Los Angeles or NYC, you’ll find the people watching on Newbury Street interesting but not intimidating. The brownstone- and tree-lined main drag is home to designer names like Armani, MJ, and Betsey Johnson. But you’ll find affordable trinkets at independent stores like Tibet Emporium, The Hempest, and one of the city’s best beauty shops, E6 Apothecary.

Don’t pass up the chance to dine outside, or try a local tea café, Tealuxe. When you’re ready for more, check out our favorite spot to dig for gently used designer goods, Second Time Around.

Stop by Boylston Street

Parallel to Newbury, Boylston Street offers access to Prudential Center, a shopping concourse with favorites like Saks Fifth Avenue, Sephora, and Lord & Taylor. The Pru, as locals call it, also has a Legal Seafood branch, a local chain known for their seafood and clam chowder.

Keep walking and eventually you’ll reach the overpass that leads to Copley Plaza (to avoid sounding like a tourist, it’s pronounced kop-lee), a complex that houses a movie theater, the Westin Hotel, famous names like Neiman Marcus, and a pampering emporium, Gretta Cole.

Hipster Yuppies Unite

Not far from Copley is the South End. Best known for its fusion restaurants and picturesque brownstones the ‘hood makes for an interesting mix of people.

Mainstay boutiques like Aunt Sadie’s sell great gifts but the burgeoning art zone, SOWA (South of Washington Street), offers the best bargains. Open studios are great places to start an art collection.

Keep in mind the South End is one of those areas that changes from adorable to barren in mere blocks.

Charming Charles Street, Beacon Hill

Charming Charles Street—Beacon Hill, arguably one of the most charming areas of Boston, is home to a upscale restaurants and cafes and oodles of boutiques. But its main draw are many havens for aspiring sommeliers and antique collectors

Though few clothing boutiques offer bargains, you can find fun books and accessories at Flat of the Hill and modern home goods at Koo de Kir.

Fulfill Ivy League Dreams

Harvard Square isn’t quite what it used to be, but it’s still an entertaining destination with old men playing chess at the Au Bon Pain, hopeful parents taking family portraits on the in Harvard Yard, and street kids
camping out in The Pit.

The main drag offers an array of clothing and bookstores; forego B&N for the Harvard Book Store. Pick up fun gifts at Black Ink, and peruse the crowded racks of the Oona’s, an old-school thrift shop.

For small luxuries, head to Brattle Street. Colonial Pharmacy is an area veteran with an extensive selection of imported fragrances. Harnett’s has a great selection of wellness products including natural beauty products. Burdick Chocolates offers a decadent place to rest — gourmet sweets are always worth an extra penny.

If you have comfortable shoes, stroll Massachusetts Avenue from Harvard Square to Porter Square. Along the way, you’ll find low-key clothing shops, great Asian restaurants, and Barefoot Books, a local favorite for children’s books.

Be Adventurous

It usually takes a new friend to break our mundane fashion routine. Every Boston-area teen frequented The Garment District in Cambridge’s Kendall Square during their punk stage.

If bins of $1 used t-shirts don’t excite you, imagine racks of funky vintage frocks and rooms full of amazing potential Halloween costumes.

Be a BU Student

Head to Packard’s Corner via the B streetcar line. Stop at the Commonwealth Avenue Jasmine Sola warehouse store and then head to the Allston branch of Boston’s largest Asian supermarket chain, Super 88, for a bite. Shop for exotic food from canned lychees to fresh fish and then prepare to be overwhelmed.

The food court houses about 10 kiosks proffering nearly every type of Asian food imaginable including Korean Indian, Thai, Chinese, and Japanese. End your day on a sweet note with an exotic Bubble Tea.

Something for the Fellas

Even if you’re not a sports fan Red Sox memorabilia is a must. Head to Twins on Yawkey Way for the goods and a peek at the park.

Boston is Very Cold

Try to avoid going for a huge shopping excursion in the middle of winter. It’s much more fun to meander without the threat of frostbite. The Cambridge Side Galleria is a huge mall that’s within walking distance of the Museum of Science, which has a large gift shop and an Imax Theater.

Rent a Car

Drive around everywhere when at all possible!

You can even try ZipCar for day. Otherwise, master the “T”, Boston’s subway alternative.

Whatever you do, avoid the cabs, which are super expensive.

Boston’s Top Shop

Second Time Around, 76 Newbury Street, Boston, MA 02116

Phone: 617-247-3504

Second Time Around boasts a selection of contemporary new and resale designer clothing. This store can be hit or miss, which explains why you’ll have to come back “a second time around.”

When this store is hot, well…it’s really hot. Thanks to increased demand, they added locations in Beacon Hill, Harvard Square, and the suburbs. Known to sport Jimmy Choo, Seven and Rebecca Taylor on any given day, you must go with time on your hands to sort through the racks.

More Boston Information


Sunday 13th of February 2011

Sadly, Jasmine Sola is not more.


Thursday 21st of September 2006

I would have to add one of my personal faves, Filene’s Basement (think Nordstrom Rack or Ann Taylor Loft). They recently opened a second location on Boylston Street with lots of reasonably priced cashmere, but the original store in Downtown Crossing remains a classic with its descending date system (anything before X date is 25% off, 50% off or even 75% off), like the color-coding at Second Time Around. Downtown Crossing also has H & M, DSW and Payless all in close proximity.

P.S. Driving in downtown Boston is highly discouraged (traffic can be nightmarish!). The T will get you everywhere you need to do, with the exception of the outlets out in the suburbs.

Mimi Froufrou

Thursday 25th of May 2006

Sadly, Harnetts is now closing down, if not already closed down by now. They were selling some of their last wares when I visited them last Saturday.

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