The fall season is without a doubt my favorite time to visit Boston. Despite being a city, it offers some nice fall color, perfect weather for walking around, and it just feels so cozy. In other words, the autumn vibes are on point here!
I’ve been to Boston in the fall season many times over the years, so I’ve really gotten my packing and outfits down to a science. This post will cover what I typically wear in Boston to stay comfortable, while also looking put-together, plus I’l recommend things you’ll want to pack and NOT pack for a stress-free trip.
And with that, let’s get started!
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What To Actually Wear In Boston This Fall – General Tips
Boston is a very casual city, and you don’t often see people dressed up unless heading to work. It’s also a very walkable city, especially the main downtown area where most visitors explore. So in general, it’s best to dress for comfort over style.
My general Boston fall outfit formula is jeans, sneakers, a top or sweater, light jacket, and baseball cap. That’s pretty much it. There have been times I’ve dressed a little nicer to do something like afternoon tea, and I’ll usually lean more into a classic preppy style a bit. But even then, it’s jeans and sneakers to stay comfortable while I was around.
The only exception would be if you’re heading out to a nice dinner, or a show, where dressing up a bit more is something you’ll want to do.
Boston Fall Outfit Ideas & Inspiration
A Classic Trench Coat Styled Different Ways
This is honestly what I wear most often when visiting Boston in the fall. A trench coat automatically looks and feels more put together, making it easy to look good while staying comfortable. They’re also lightweight, and often water-resistant, making it a great fall staple to have in your closet (not just for a visit to Boston!).
For the most casual look, I’ll pair it with a long-sleeved t-shirt (for me, it’s usually white and blue stripes), jeans, sneakers, and a baseball cap. If it’s extra chilly that day, I’ll also throw a lightweight sweater over my shoulders so I have another layer to put on if I get cold. Plus, it adds a nice visual interest that’s actually functional.
I’ll also sometimes swap out the extra sweater over my shoulders for a nice fall scarf. The one in the picture is old, but it was from Anthropologie by the brand Maeve (if you want to try to find it on Poshmark or eBay). And sometimes, a cute fall headband replaces my baseball cap. Just depends on my mood 😊
Links To Similar Styles:
→ Everlane Way High Jeans (I’m wearing an older version of these)
→ Adidas Sneakers
→ Trench Coat (I’m wearing an older version of this Gap one)
→ Similar Long-Sleeved Striped T-Shirt
→ Purse
→ Scarf – not the one I have, as it’s sold out, but I really love the colors on this one!
Barn Jacket & Sweatshirt
Another one of my go-to Boston fall outfits is jeans, sneakers, a sweater or sweatshirt, and a barn jacket. This is another great casual outfit that’s perfect for walking around while staying comfortable.
Depending on the weather, I’ll add a turtleneck base layer on the sweater or sweatshirt, and the barn jacket is such a nice staple to also have in your fall wardrobe. Barn jackets pretty much go with everything, and work really well with Boston fall weather.
Links To Similar Styles:
→ Everlane Way High Jeans (I’m wearing an older version of these)
→ Adidas Sneakers
→ East Coast Sweatshirt (they have a shop in Boston!)
→ Barn Jacket – mine is old, but this one from L.L. Bean is fantastic
→ Purse
A Little Preppy
As mentioned, sometimes I like to lean into a more preppy outfit. Since Boston is home to over 30 colleges (plus more if you count the Greater Boston area!), the fall season almost feels very nostalgic and collegiate because of the college kids and campuses everywhere. It’s kind of fun to dress up like you’re heading off to your first day of school with a bench of freshly-sharpened pencils and crisp notebooks – just with a slightly more grown-up take on it 😉
For this kind of outfit idea, I love to break out a sweater vest! I know, it’s not everyone’s cup of tea, but I love a good sweater vest paired with a button-down shirt. It’s so easy and comfortable to wear, and looks really polished. You can then throw a trench coat on, or keep it over your shoulders – or even the barn jacket would look great with this.
Links To Similar Styles:
→ Everlane Way High Jeans (I’m wearing an older version of these)
→ Adidas Sneakers
→ Trench Coat (I’m wearing an older version of this Gap one)
→ Vest – I’m wearing an older style by Boden that’s sold out, but the one I liked is similar and more affordable.
→ Vest Option 2 – This is a nice option in a solid, with different color options.
→ Button-down light blue shirt
→ Purse
A Good Purse Is A Must
When walking around any city, a good purse or bag is really a must-have. Because Boston, especially, is so walkable, you’re likely to be away from your hotel room for hours at a time. Having a good purse that’s large enough to carry what you need, but small enough to not be an annoyance all day, is really helpful (in my experience, anyway).
After years of trying all kinds of purses, both for every day and travel, I’ve landed on this one. And honestly, it’s perfect. I’ve even gotten my mom hooked on it, and it’s all she ever uses now, too. I use this purse for both every day and travel, and own it in a few different colors to swap out seasonally because I just don’t want to use any other purse anymore.
What I love about this one is that it’s the perfect size (not too big or small), holds everything I need (wallet, keys, sunglasses, medications, lip balms, etc), and the size of it doesn’t encourage me to have too much stuff that I’ll never use. I also love the front quick-access compartment, which I’ll use for my keys and phone.
The only downside to this purse is that the strap it comes with is short, and it will wear more like a sling bag than a true crossbody. So, you have to buy a separate, coordinating longer strap, which is an added cost when purchasing. I find it to be worth it because I know I won’t be buying any other purses for a long time, but that’s something you’ll want to consider.
Boston Fall Outfits: What To Pack
Here’s a quick summary of what I suggest you pack in regard to clothes for a fall trip to Boston:
Comfortable sneakers: This is what you’ll primarily wear your entire trip to walk around, see the sights, etc. Since many of Boston’s sidewalks in neighborhoods like Beacon Hill and the South End have uneven brick and cobblestone, you’ll be really glad to have on flat, comfortable shoes.
Fall boots: If you’re in Boston for longer than a day or two, and need to have a pair of shoes for going out at night, I’d say your second pair should be some fall boots. I would keep the heel flat, or very low and chunky, so that you can easily walk on uneven brick/cobblestone streets. These can also be dressed up for a nice dinner out (unless you’re doing something very upscale, in which case you’ll want to consider packing different shoes to go with that outfit).
Jeans: Honestly, this is pretty much all I wear for bottoms in the fall. Much like above, unless you need a super fancy outfit for an event or something, you can easily dress up jeans to go out to dinner, too.
Long-sleeved tops: These are perfect if Boston is forecasted to be on the warmer side, as you can easily throw on a coat for added warm, but won’t be too hot during the afternoons.
Sweaters & sweatshirts: This is what I’d pack if your fall weather is forecasted to be typical chilly weather. You can add a base layer underneath, too, in case it warms up, and then throw the sweater/sweatshirt over your shoulders.
Outerwear: If there’s lots of rain in the forecast, I would plan to bring a waterproof rain jacket, in addition to a regular fall jacket, if your suitcase allows the extra room.
Purse: As mentioned, this is my favorite purse because it’s pretty small, but holds a lot while staying organized. But if you already have a purse that you love, bring that.
Accessories: Baseball hat (or, you could buy one while in the city), fall scarf, or a knit beanie if the weather is forecasted to be cold. You’ll also want to pack your favorite sunglasses for sunny afternoons.
Boston Fall Outfits – Answering Your Questions
Do I Need A Warm Coat For The Fall?
Boston has a reputation for being super cold, but honestly in the fall, you won’t need a heavy winter coat yet. In fact, it tends to be warmer than places up in the mountains, so I recommend layers, and a regular fall coat (like a trench or barn jacket). You’ll likely feel too hot in a winter coat, unless you’re from a very hot climate and not used to the cold.
Is The Fall Season Rainy In Boston?
It’s rainier than summer, of course, but it shouldn’t rain every day. October sees, on average, about 2-3 extra days of rain compared to the summer. Weather websites say to plan for about 9-10 days of rain per month in the city during September, October, and November.
What Do I NOT Need To Pack?
Heeled shoes: Trust me, you’ll immediately regret it. As mentioned, many sidewalks in the city are uneven brick and cobblestone. Not so much in the main downtown area, but definitely in places like Beacon Hill and the South End. Just pack comfortable sneakers and/or fall boots that you know don’t give you blisters.
Umbrella: If there’s rain in the forecast for your trip, I would leave the umbrella at home, and opt for a raincoat. Boston is a very windy city (windier than Chicago!), and an umbrella will likely blow around too much. Plus, if you really need an umbrella, many hotels offer them to guests staying there.
You can maybe leave the dresses at home: This one is personal preference, and I’ve definitely worn skirts and dresses in Boston in the fall – even just to walk around in. It kind of depends on the weather. If it’s super windy, you’ll regret it, and spend a lot of time holding it down so it doesn’t blow up. However, if it’s a sunny and calm day, a dress/skirt with tights is a great outfit idea.
That’s A Wrap On Boston Fall Outfits
And there you have it – my tips and suggestions on what to pack for a fall trip to Boston, including some outfit ideas to get you started! I hope you’ve found this helpful as you decide what to pack for your getaway. Remember, comfortable shoes are the most important thing, and when in doubt, keep it casual.
