What to Wear in Boston This Fall

Is there anything better than Fall in New England? Crisp breeze, cozy scarf, and some time on a sailboat? Sign me up! Wondering what to wear while you're devouring that delicious chowder? Check out these Boston outfit essentials!

Disclosure: some of the links below are affiliate links. If you purchase a linked item, I will make a commission, at no extra charge to you. I received a dress from Wool& for free. As an Amazon Associate, I earn from qualifying purchases. Updated August 2022

Packing for a trip to Boston?

Who doesn't love Boston? I may be a massive Indianapolis Colts fan, but I was also an Early American History Major (yes, that's a thing), so obviously I'm obsessed with one of America's most historic cities! 

Paul Revere House, Boston's Freedom Trail

From narrow, cobblestone streets and stunning townhouses, to its gorgeous Harbor and world-famous fall colors, Boston and its surrounding cities really do have it all.

Most, but not all, of the time I've spent up there has been in Autumn, and it just keeps me coming back for more! It's definitely the time that New England shines, with the most delicious apple cider you can imagine and cups of chowder that are worth every, last calorie. Honestly, it really is a bit like a Pinterest Fall board has come to life and splashed those orange leaves and cozy autumnal feels all over the place. Fall is the perfect time to visit - and once the weather cools off, you can simply walk for miles exploring every tourist sight this great city has to offer!

So let's get to it! How to pack for Boston in the Fall!

What to wear in Boston in Fall:
​Comfortable shoes

Boston is consistently rated as one of America's "most walkable" cities, both for residents and for tourists. As with any city, strolling the streets is a huge part of the enjoyment of the place. But when you're visiting a city that has one of the greatest tourist-centric walking paths anywhere around, you're not going to want sore feet holding you back! And, of course, traffic is a bit of a nightmare, so if you can walk rather than drive, I definitely would recommend hoofing it!

For me, packing for Boston in the Fall is about loafers and booties. In early Fall, such as this September, I think full on riding boots, my usual go-to for "shoulder season" travel, would have been a bit too toasty on those over-worked feet. 

So, it's a pair of loafers, such as either top siders (a New England classic!) or basic leather loafers, and those classic, waterproof booties! I like to keep it preppy with those loafers even in the evening, but if you're feeling more formal, remember your toes might get chilly with an open-toed shoe in the evening, even in the Fall!

What to wear in Boston in Fall:
​A light jacket

Walking the Freedom Trail!

Depending on where you're visiting New England from, the weather during September and October in Boston can be very different from what you're used to! For us in the Mid-West, it's still often quite warm during early Fall. For example, it's 86 degrees in Indianapolis on the day I'm writing this in mid-September.

We enjoyed phenomenal weather in Boston in September, in the 60's mostly, though it did get a bit warmer toward the end.

Be sure to pack a light coat for those days, and nights, and of course in the event of any rain. I felt super-chic in my handy trench coat, which gave me the comfort of a windbreaker, while helping me stand out from the tourist crowds! Also, it's of course, super appropriate if you do end up with a rainy day!

If trench coats aren't your thing, I'd go for a classic wind breaker. I love this Army green version that combines the style of a Barbour coat with the lighter-weight of a windbreaker (without the wax coating).

What to wear in Boston in Fall:
​Scarves, scarves, scarves!

I suppose wearing a scarf in New England in the Fall kind of goes without saying? But if there's a time and a place for a big, chunky, scarf, this is it!

​What to wear in Boston in Fall:
​The right jeans

Can't go wrong with a handy pair of jeans when you're exploring the North East! 

For my European friends who may be confused by this recommendation, especially since I endlessly drone on about jeans in Europe, Americans are far more casual than Europeans, as you likely know, especially on vacation. Even in a big city like Boston, you'll fit right in in jeans, even at dinner. American restaurants rarely have dress codes that forbid jeans, unless you're going to the oldest steak house in the city, or a private country club, and even then, rules are often not strictly enforced. 

​What to wear in Boston in Fall:
​All of the sweaters

The Boston Public Library

Who doesn't love a good, cozy sweater? I am all about the sweater-and-shorts combo when I can rock it, and occasionally in late summer/early Fall in New England, I can get away with it! Or, if it's more of a pants day, obviously a light sweater will keep you comfy while you're hiking all around Boston!

For that nautical vibe, check out striped shirts from French style classic, Saint James. Perfect under that light jacket!

What to wear in Boston:
​A lightweight purse

Especially if I'm going to be taking my coat on and off, I like to have a purse, rather than trying to cram all of my possessions into my pockets and hoping they don't fall out.

This most recent trip, I carried my LV Neverfull and it was probably a bit too big for this particular adventure. Generally, I'm all about Longchamp on vacations, so that's what I would recommend for this type of trip - looks nice during the day, but it's lightweight and zips, so your stuff is nice and safe in there. I can also generally cram a few souvenirs in before the day is done! I did see *a lot* of tourists with Longchamp backpacks. I'm not a huge backpack fan myself, maybe because I'm paranoid that people will steal my stuff, or because I'm not used to wearing one and I'm afraid I'll bump into things in a museum, but if that's your style, you'd definitely fit in!

What to wear in Boston:
​A comfy dress

On a gorgeous day in autumn in Boston, who doesn't want to sport a classic dress? Add tights/leggings, a scarf, and a pair of classic, preppy riding boots (or booties, depending on the weather), and you'll be East Coast chic! 
​
My most recent find is the Clara Shirt Dress from Wool&. It's lightweight, but still warm, and wool that doesn't itch or get that stale wool smell in drizzle and, it's got a great, structured look, with pockets and a tie at the waist. 

Thanks so much for stopping by!

And, as always, have an amazing trip to Boston, and don't forget to pack those essentials! And don't forget to sign up for the newsletter, while you're here! Happy travels! xx

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