Despite having four distinct seasons, Boston is arguably the most beautiful in the fall. As the leaves change colors, a gorgeous backdrop of red, orange and yellow fall foliage somehow blends seamlessly with the historic architecture of this beautiful city.
In addition to an up-close view of the stunning scenery, a trip to Boston in the fall offers an opportunity to take a stroll down Newbury Street, visit the Freedom Trail, check out the Boston sports scene, or enjoy the view of the Charles River.
Fall in Boston is relatively mild, not too cold or too hot. Thus, a trip to Boston in the fall also offers the perfect opportunity to layer up and put together some outfits that will keep you comfortable in the mild temperatures!
With the right outfit, you can enjoy all that Boston has to offer without sacrificing comfort and your personal style. So today, I’m sharing a roundup of my favorite outfits to wear in Boston in the fall. Hopefully this list will inspire you to visit Boston and help you better prepare your Boston packing list.
Without further ado, let’s dive right in!
What to Wear in Boston in the Fall: Outfit Inspiration
Cozy Sweaters with Jeans
There is just something about fall fashion that I love and if there is one “staple” outfit, this is it. A cozy sweater, whether fitted, oversized, or somewhere in between, is a must-have when spending time in Boston in the fall. For the ultimate fall look, grab a cozy sweater, a good pair of jeans and your favorite boots, and head out to see what all the city has to offer.
Plaid Turtleneck with Light Wash Jeans
Tan Sweater with 90s high-waisted jeans
V-Neck Tunic Sweater with Dark Wash Skinny Jeans
Camel Sweater, Camel Boots, and White Jeans
Off Shoulder Striped Sweater with Skinny Jeans and Fedora Hat
Long Sleeved Tops with High-Waisted Jeans
I love this combination because long sleeved tops can be just as casual or dressy as you want them to be. When paired with high-waisted jeans, long sleeved tops create a slimming, flattering silhouette that works great with just about any pair of shoes in your closet. From running errands around town to a night out with friends, this outfit is as versatile as they come.
White Puff Sleeve Top with Dark Skinny Jeans
Black Long Sleeve Mock Turtleneck Top with High Rise Ripped Jeans
Fitted Tops with Paper Bag Pants
What’s not to love about a good pair of paper bag pants? They can be dressed up or down and, aside from the obvious leggings and sweatpants, they’re among the most comfortable pants you can slip into. For a balanced look, wear a fitted top with a pair of paper bag pants. A leather jacket completes this easygoing look.
Paper Bag Pants with a Leather Jacket and Booties
Tank Tops and Shackets
When it comes to fall fashion in Boston, tank tops are better used as layering pieces. For a laidback look, slip on a tank top and wear it underneath a jacket. Then, pair with your favorite leggings. Or, add a tank top underneath your favorite flannel or shacket for an extra bit of warmth on cooler days. A good shacket is a must-have for those mild days when a shirt isn’t enough, but a jacket is too heavy.
Drape Front Faux Suede Jacket with Crop Tank Top and Black Leggings
Plaid Wool Button Down Shacket with Skinny Jeans
Open Front Cardigan with Black Crop Tank Top and White Jeans
Long Skirts and Denim Jackets
Worn under a denim jacket, a long skirt with a tank top is a great option for days that start cool and turn warm by the afternoon. Which, by the way, is typical in Boston in the fall. You can start your day off warm and cozy, but then slip off your jacket and stay right on trend as the day heats up. When it comes to shoes, I love to pair long skirts with sneakers to keep the look more comfortable and casual.
Polka Dot Long Skirt with Tank Top and Fitted Denim Jacket
Pink Maxi Skirt with White Sleeveless Top
Leather Jackets
A leather jacket is a great outerwear option to wear in Boston in the fall. I adore my brown leather jacket, which looks great with skinny jeans and either a white or black top underneath. This is a look that easily goes from day to night, making it a necessity as you pack for Boston.
Brown Leather Jacket with White Top
Brown Leather Jacket with Black Top, Light Wash Jeans, and Black Boots
My favorite Fall picks from Revolve
Revolve is a high-end online fashion store offering some of the trendiest and stylish looks in every season. I believe in investing in staple pieces that you can mix and match throughout the seasons and wear in years to come. These picks are special because they offer a bit more formal and fashion-forward style to stand out in any fall occasions.
Mazzy Bodysuit
Kiera Sweater
Dutton Cropped Jacket
Jennie Flannel Dress
Cynthia Jogger Pants
The Hanriette Pant
Adonia Zipper Front Page
Tips on What to Wear in Boston in the Fall
Here are a few things to keep in mind when deciding what to wear during your trip to Boston in the fall:
Dress in Layers
Dressing in layers is especially helpful on days with cool, crisp mornings that turn into bright, warm afternoons. Tank tops and jackets are two essential layering pieces that I pack for every trip. It’s also important to pack layers like socks, cardigans, long-sleeved shirts, and maybe even a scarf or two.
Pay Attention to the Weather Forecast
The weather forecast just may be the one factor that ultimately decides what you wear each day. Whether you’re expecting rain, snow, or warm sunshine, you should plan ahead and ensure you’re always checking the weather forecast as you put together your outfits. And don’t forget the accessories; you don’t want to end up stuck in the rain without an umbrella.
Don’t Sacrifice Comfort for Style
Even the most stunning outfit will instantly become less appealing if you feel miserable in it. That’s why I try not to sacrifice comfort for style. This is especially true if you plan on doing a lot of walking or other outdoor activities. No matter where I travel, comfortable shoes are a must.
Be Intentional with Your Color Palette
The leaves of the trees that line the streets of Boston usually start to take on their familiar fall colors around the second or third week of September. If you are planning to spend some time in Boston in the fall and want to take some gorgeous, Insta-worthy photos, consider how your clothes will fit into the autumn aesthetic. Deep oranges and yellows are a great choice. When styled with browns, tans, and other neutrals, you’ve created the perfect color palette for fall.
Don’t Forget the Accessories
An outfit almost feels incomplete without a few accessories. Whether it’s a simple necklace or an oversized scarf, the right accessories can add flair to even the most simple outfit. So, as you curate your perfect fall wardrobe for Boston, make sure to grab a few comfortable and versatile accessories.
Enjoy Boston in Style
Boston is such a beautiful city to visit any time of year, but there’s nothing quite like the city in the fall. If you couldn’t tell already, I think fall is the best time to visit this amazing east coast destination. With the right wardrobe pieces, you can enjoy all that Boston has to offer, but in style.
