What to Wear in Boston, According to a Fashion Expert

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Boston is a city that's full of surprises. History lovers can enjoy traversing the cobblestone streets of North End and touring the modern masterpieces at the Institute of Contemporary Art. Meanwhile, fashion enthusiasts will find plenty of shopping options at Seaport, where brands like Everlane and Grace Loves Lace meet local favourites at The Current, home to an always-evolving lineup of lifestyle brands.

"Boston gets a bad rep for having bad fashion, but I don't think that's the truth," says Alison Barnard O'Brien, founder and owner of the Boston boutique Injeanius. Having been on the frontlines of Boston fashion for nearly two decades, O'Brien has seen trends come and go. What really matters to most Bostonians in relation to their personal style can be boiled down to a few key questions, she explains.

"There's so many people dressing on-trend and they're thinking, 'Is it winter-proof? Is it accessible? Can it take my everyday and step it up?'" O'Brien says. "You can be in your denim, but you add those personal pieces that help elevate it."

One non-negotiable item that should be part of your Boston packing list: a hat. This is especially true if you're visiting during wintertime. "You need a good hat, whether it's a beanie or something else," O'Brien says. "You've gotta cover up the noggin."

And don't forget the proper outerwear. When those blistering Boston winds hit your body, you'll want to have every inch protected from the elements.

"You need a coat that covers your bum," O'Brien says. "The covering of the bum is very important in keeping you warm around here. I also firmly believe in some cashmere — cashmere gets me through our winters."

Reference the agenda ahead for what to wear and what to do in Boston.

Where to Stay in Boston: The Envoy Hotel
Boston Seaport

Where to Stay in Boston: The Envoy Hotel

With incomparable waterfront views of the Boston Harbour and easy access to Logan Airport and the bustling Seaport development, The Envoy Hotel is a clear frontrunner for your Boston accommodations. Begin your day with breakfast at the hotel restaurant, Para Maria, which serves Latin-inspired dishes like huevos rancheros and Mexican hot chocolate French toast. After a day of adventuring, reserve an igloo at the Lookout Rooftop and sip on specialty cocktails with the sparkling Boston skyline in the background.

Lezé the Label Athena + Kendal Set in Matcha
lezethelabel.com

Lezé the Label Athena + Kendal Set in Matcha

A matching set is a surefire winner. This AAPI-owned brand makes fabric that's so buttery soft, and the colours are neutral enough to work with your existing wardrobe. Pair this matcha-hued set with classic Ugg boots for an ultra-cosy look, or get a little dressy with heeled, fur-lined booties and an embellished headband.

Lezé the Label Athena + Kendal Set in Matcha ($175)

Where to Sightsee in Boston: L.L.Bean Outdoor Discovery Program
Boston Seaport

Where to Sightsee in Boston: L.L.Bean Outdoor Discovery Program

To really get a feel for what Boston has to offer, take to the water. Head to the dock at the Boston Children's Museum and rent a kayak anytime between June and September through the L.L.Bean Outdoor Discovery Program. Be sure to make a reservation online, though some walk-ins are accepted depending on availability. You'll receive everything you need (flotation device, kayak, paddle) before setting out for a guided tour of the area. Kayaking courses are also available during select times on Fridays through Sundays.

Alder Open Air Pant
alderapparel.com

Alder Open Air Pant

These pants are specially designed for outdoor activities of all varieties, from hiking to running to kayaking and everything in between. They've got just the right amount of stretch to be comfortable, and the built-in side pockets are perfect for stashing cards, cash, lip balm, and other essentials.

Alder Open Air Pant ($155)

Where to Eat in Boston: North End
Getty | Boston Globe

Where to Eat in Boston: North End

For those craving Italian cuisine, look no further than Boston's North End. Also known unofficially as Little Italy, this neighbourhood is brimming with bakeries, trattorias, pizza spots, gnocchi hangouts, and more. Grab a cannoli and a cappuccino — the ultimate winning combo — at Modern Pastry. Make dinner reservations at Mamma Maria and don't forget to snap a photo in front of its picturesque, vintage-inspired storefront.

Polo Ralph Lauren Twill Trench Coat
ralphlauren.com

Polo Ralph Lauren Twill Trench Coat

A classic camel trench coat is an ideal outerwear companion for a jaunt through this idyllic, centuries-old neighbourhood. Pair yours with slim-fit, dark denim jeans, a black turtleneck, and timeless leather loafers for an ultra chic ensemble.

Polo Ralph Lauren Twill Trench Coat ($598)

Where to Explore Art in Boston: Institute of Contemporary Art (ICA)
Boston Seaport

Where to Explore Art in Boston: Institute of Contemporary Art (ICA)

Calling all art lovers, this museum is one you won't want to miss on your next Boston trip. Its iconic building on Boston's waterfront is a visual masterpiece on its own, offering a scenic walk into the museum itself. The ICA helps create new ways of engageing with the world around us through immersive exhibitions and programs. Now through Feb. 26, 2023, one such exhibit is "To Begin Again: Artists and Childhood," which examines the influence of children and childhood on visual artists from the early 20th century to today.

Madewell New Balance Suede 327 Sneakers
madewell.com

Madewell New Balance Suede 327 Sneakers

A day filled with walking and standing calls for comfortable sneakers that can be dressed up or down. These New Balance shoes are casual enough to be worn with jeans and a T-shirt, yet the suede detail offers a dressier feel that will complement a pantsuit or skirt set.

Madewell New Balance Suede 327 Sneakers ($90)

Where to Shop in Boston: Snowport Holiday Market Pop-up
Boston Seaport

Where to Shop in Boston: Snowport Holiday Market Pop-up

Want to do some shopping while in Boston? If you're staying at The Envoy Hotel, take a stroll a couple blocks down to the Holiday Market at Snowport. This European-style, open air holiday market showcases more than 120 small businesses, where shoppers can discover one-of-a-kind gifts and treats, nearly all of which are locally made in the Boston area. During the holidays, there's an appropriately themed tree market, where Christmas trees, wreaths, tree stands, and lights are for sale.

Adrienne Landau Cable Knit Beanie
shopbop.com

Adrienne Landau Cable Knit Beanie

In between scoping out the stalls of locally made apparel and accessories and sipping on hot chocolate, keep your head and ears nice and toasty. This cable knit beanie is casual-yet-chic and easy to match with your other winter whites.

Adrienne Landau Cable Knit Beanie ($35)

What to Do in Boston: Stroll Through Cambridge
Getty | Brooks Kraft

What to Do in Boston: Stroll Through Cambridge

You don't have to be a university student to enjoy the sights of Cambridge. The neighbourhood's brick buildings, riverside scenes, and generally collegiate atmosphere make for a day filled with relaxed, loose "plans." Think: a walk by the river followed by hitting up the local vintage shops such as We Thieves and Great Eastern Trading Co. Then, round out the day with a treat from Flour Bakery + Cafe.

Abercrombie & Fitch Easy V-Neck Sweater
abercrombie.com

Abercrombie & Fitch Easy V-Neck Sweater

Understated is best with your general Boston wardrobe. A standard V-neck sweater is a favourite for its layerability. Try pairing it with wide-leg trousers and leather loafers to sightsee; wear it over a slip dress and jeweled heels for date night.

Ahead, check out additional fashion items to shop for a trip to Boston.

Abercrombie & Fitch Easy V-Neck Sweater ($33.60, reg. $70)