Newbury Street
As the hotspot of Boston shopping, we have to start with the glorious Newbury Street. With eight blocks of money-spending galore, this street checks almost all the boxes. It is a harmony of a shopping experience, balancing clothing stores with food joints, and high-end boutiques with the more college-budget-friendly stops. It is also there for all of your errand-running needs, including the perfect insta pic, because you can never go wrong with rows of renovated brownstones. I like to start at the Mass Ave. end because you can get your shopping fix within the first block, then leisurely stroll the rest of the street, popping in where you please, grabbing a coffee (or two, or three), and window shopping at the designer stores as you get closer to the Boston Common.
The essentials: Brandy Melville, Zara, Anthropologie, H&M, LF, Muji, and Newbury Comics
Pit stops: Trident Booksellers & Cafe, Mother Juice, Georgetown Cupcakes, and Ben & Jerry’s
Window lusting: Tiffany & Co., Burberry, Chanel, and the School of Fashion Design
Faneuil Hall
On the other side of the Boston Common, Faneuil Hall is a hub for more than just the everyday shopaholic. It injects the shopping experience with some fun, thanks to the rotating street performers, the raging dive bars, and, of course, Quincy Market. You’ll be buying much more than the latest trend here, instead pulling out your wallet at the scrumptious food stands ranging from seafood to candy apples. There are also the tourist-friendly stops inside the market that are sometimes worth checking out for the occasional Boston sweatshirt or framed watercolor of an iconic city scene. You also can’t leave without taking at least one picture with a historic artifact (I’m always a fan of the Larry Bird shoes).
The essentials: Urban Outfitters, Sephora, Uniqlo, and Yankee Candle
What you really came for: Mmmac N’ Cheese, Wicked Good Cupcakes, and Wagamama
Where to end your day of shopping: Wild Rover, Bell in Hand, Hong Kong, and Cheers
Downtown Crossing
Now more relevant than ever, the shopping district of Downtown Crossing is small enough to feel manageable and diverse enough to feel unmissable. Dropped in the center of the theatre district, Downtown Crossing may not have the best photo ops, but it does have some of the best culture. Weave your way through the side streets to discover secret hot spots such as quaint used book stores and convenience stores that sell Halloween costumes in October. Stop for coffee on literally every street, and make your choice depending on the vibe you’re going for (but Caffe Nero is always the right choice). Grab a hotdog from a street vendor then dig into the shopping, because I promise that you can’t spend less than an hour here–and you definitely won’t go home without at least one shopping bag.
The essentials: Primark, Forever 21, Brattle Bookshop, Bath & Body Works, and Davids Tea
For a caffeine boost: Caffe Nero, Thinking Cup, Ogawa Coffee, and Boston Common Coffee Co.
Worth noting: Sweet, Roche Bros., Kenmore Army & Navy Store, and Cex
Harvard Square
It’s worth hopping across the Charles for an afternoon of shopping a square that just makes you feel smarter and more significant. Just steps away from the Harvard campus, Harvard Square comes with its own unique shopping experience, complete with shops you won’t be able to find in downtown Boston. It makes up for Boston’s lack of thrifting opportunities (though the iconic Garment District is still an uber drive away), and gives its chain and independent stores enough charm to seem special. Rich with red bricks, cozy benches, and not-to-be-missed dining opportunities, this shopping district proves that those Harvard kids are doing a lot more than just studying all the time.
The essentials: Lush, Planet Records, Black Ink, and The World’s Only Curious George Store
Those other kind of essentials: Good Vibrations, Forty Winks, and Chameleon Tattoo
If you’ve shopped until you dropped: Brattle Theatre, The Sinclair, and Beat Brasserie