16 Best Places to Shop in Boston, Massachusetts

This small, personal store showcases well-made, comfortable lines that cater to women who cannot walk into a fitted size-4 suit—in other words, most of the female population. The designers found here, such as Nicole Miller, Autumn Cashmere, and Cambio, are fashionable yet realistic.

Founded in 1818, Brooks still carries in its nationwide shops the classically modern styles that made it famous—old faithfuls for men such as navy blazers, summertime seersucker, and crisp oxford shirts and similar styles for women and kids (4–16 years). Its Newbury Street store offers the hipper Fleece collection with both a bright affordable line and a high-end designer line aimed to appeal to less conservative shoppers. There's another location at 75 State Street.

This spacious 10,000-square-foot branch of the Parisian couture house (complete with custom sofas upholstered in Chanel tweed and a 20-foot-high strand of cascading glass beads) carries suits, separates, bags, shoes, cosmetics, and, of course, a divine selection of little black dresses.

Find weekend casual outfits, jeans, silky shifts, and even party attire at this feminine boutique. Accessories are not overlooked, as Crush offers jewelry and handbags that will dress up any ensemble.

The edgiest clothing boutique on the Hill, December Thieves stocks fashion-forward, contemporary, emerging designers and brands from Europe, Asia, Latin America, and other places across the globe. Find a curated and wildly fun array of apparel, scarves, handbags, jewelry, beauty products, and home decor.

True to its name, this locally owned specialty store curates designer party dresses, but the selection doesn't end there. Women will also find tops and pants, shoes, accessories, handbags, and even a few home goods items.

Major discounts on high-quality (and big-name) shoes for men and women draw savvy Boston shoppers to this branch of the chain DSW, also known as Designer Shoe Warehouse. Everything from Nike to Prada can be found at varying discounts—sometimes up to 90% off.

This boho-chic boutique brims with cotton T-shirts, floral dresses, and vintage-inspired jewelry, along with whimsical gift items, like handmade keepsake boxes filled with colorful images and antique baubles.

Founded in 1907, this national men's chain has crisp suits, dress shirts, and leather shoes for the conservatively well-dressed male everywhere. And gents, should you need a tuxedo at the last minute, rest assured: the store rents them.

Trendsetters go wild for Kate's colorful and classically whimsical dresses, as well as her handbags, shoes, PJs, accessories, and travel and cosmetics cases.

If there's a style trend out there, this small women-led, minority-owned shop sells it. Full of flirty frocks from the likes of Free People, For Love & Lemons, and Blank NYC, along with accessories like jewelry, hair clips, and bags, the packed racks of fun pieces can add confidence to chic shoppers' closets.

Inspired by the temperature-regulating materials used for NASA's astronaut clothes, three MIT students started this men's and women's clothing store that features stretchy, moisture-wicking, wrinkle-free, machine-washable slacks, shirts, blouses, blazers, and jackets designed by a former Theory designer (think clean and elegant). Interested in creating a bespoke blazer on-site? The store's 3-D print knitting machine can finish a garment in about two hours.

Cute dresses, playful skirts, and form-fitting tops make up the selection here. The Cambridge location is a little larger and easier to navigate, but Brookline houses the original.

In the heart of the South End, shoppers can step down into this small boutique celebrating the history of fashion in New England. Shoppers will find a selection of preppy staples mixed in with current trends for all genders. The boutique recently partnered with Brooks Brothers to carry the latest collection of men's spring/summer styles designed by Michael Bastian.

This too cute—and a bit bohemian—mom and kid clothing store features looks from fairly expensive, small brands, and there's no question as to its place in Beacon Hill society. This is where the neighborhood women come to buy frocks that aren't made to be worn to the office. There's also a nice selection of toys and kid gift items, including stuffed animals and sensory jars.