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what to wear in boston

What to Wear in Boston

With all the professors, students, and other academics in the city, Boston has a decidedly academic feel. You can get away with a range of styles, but if you’re wondering what to wear so as not to stand out, err on the conservative side.

You’ll notice Boston clothing has more of a professional, polished look, typical of cities in the Northeast. You can’t go wrong with the classics: cable knits, sheath dresses, sweater sets, striped T’s, tailored trousers, and even suits. Come winter, you’ll notice the goal is to stay warm above all else. Commuters wear L.L. Bean boots with suits as much as they do with jeans.

What to Wear in Boston

Filled with youth, Boston style can give off a more laidback collegiate vibe, too, making a fitted T-shirt and jeans a perfectly acceptable uniform. You’ll often find the weather dictates how much or how little Bostonians dress up. Here’s what to wear in Boston to blend with the locals.

Evening Wear

evening wear

If you plan to dine at one of Boston’s innumerable up-market spots or take in a show, pack something a notch above jeans. Cocktail-length dresses that you can dress up with heels or down with a belt make it easy to justify using space in your luggage. For men, nice pants and a polo shirt are a good option.

Anything with Elbow Patches

elbow patches

The quintessential college town makes it perfectly acceptable to don your preppiest threads. It’s the perfect excuse to pack a cardigan or sweater with a suede elbow patch .

Collared Shirts

man wearing collared shirt

In keeping with the Ivy League theme, collared shirts are one of the easiest ways to elevate jeans and polish off a look without trying too hard. (Click here for women’s collared shirts.)

Red Sox Anything

woman wearing red sox cap boston

This is a town that loves its sports teams. Throw on a Red Sox shirt at a Celtics game and you won’t get looked at twice. Male or female, a classic ball cap is your best bet.

Breathable Fabrics

breathable fabrics

Summers can get hot and in winters you’ll want to stay dry even if you’re working up a sweat going from attraction to attraction. Pack clothing in fabrics that will keep moisture off of you.

Dark Denim

man wearing dark denim
Maksim Shirkov / Shutterstock

Packing jeans in a dark rinse will help you play double-duty: exploring the city by day and dressing up for dinner by night.

Anything but Running Shoes

flats and boots

Unless you’re going for a run, save the tennis shoes for the tourists. Flats (or loafers for men) are your best bet to put on serious mileage. A boot that can tackle rain or snow is critical for fall, winter, and spring.



In winter, you’ll want something thick. In summer, a lightweight scarf can dress up a casual look.

Nautical-Inspired Gear

nautical inspired clothing

One Boston clothing trend that never goes out of style is anything nautical. Channel the city’s seafaring history with any clothing in white and navy. Stripes are always a safe bet. You can also add a rope belt to really go for the Cape Cod-inspired summer look.

Neutral Colors

neutral color palette

Timeless is the theme of what to wear in Boston, and neutral colors are your foundation. Think khaki, black, white, navy, gray, and tan.

More from SmarterTravel:

– Original reporting by Kate Sitarz

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