What to Wear to Boston in the Fall

Boston in the fall just feels right. If you’re traveling to Boston this autumn and are wondering what to wear, I’m breaking down each of the outfits I wore for my three-day visit. Planning what to wear is actually a pretty important step in preparing for your trip. When choosing your outfits, considering the climate, the landscape, and your travel plans is key to having an enjoyable visit. Get ready to explore Boston in comfort and style with these tips on what to wear for your trip.

This is your guide to what to wear for a fall trip to Boston.

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Tips on What to Wear to Boston in the Fall

Be sure to include some comfy, flat shoes. You’re bound to do plenty of walking in Boston, and with lots of cobblestone streets throughout the city, heels will not be your friend.
Temperatures can range from warm during the day to downright chilly at night. Layers will be key for staying comfortable.
Pack light by choosing versatile pieces that can be worn more than once or that layer well together. This gives you the benefit of having multiple looks that can be adjusted for the weather or any last-minute plans without having to lug around a heavy, overfilled suitcase.
Autumnal tones really fit the vibe in Boston. Wearing shades of camel, brown, burnt orange, black, and beige/cream will help set the mood for any fall photos.
Speaking of dressing for photos, Boston is a pretty casual city, but the historic backdrops lend themselves to some slightly elevated looks. I was able to marry the two by choosing casual base items, like black denim or a simple knit, and then building on those with pieces like a wool blazer or beret.

What I Wore for 3 Days in Boston

Wearing a brown blazer, Gaspard jumper, black jeans, and loafers at Trinity Church in Boston

Wearing a brown blazer, Gaspard jumper, black jeans, and loafers on a fall day in Boston.

Outfit No.1

Sézane’s Gaspard jumper is one of my favorite pieces to pack for a trip because it’s so versatile. It’s designed to be worn with the buttons in the front or the back, and it’s cozy yet thin enough to layer without being bulky. For this outfit, I wore the light beige version with the buttons facing back. The wool plaid blazer was perfect for layering over the top when the temperature dropped.

Outfit details:

Taking a walk on an October fall day in Boston wearing a Gaspard jumper and black jeans.

Layering with a wool shacket when it gets cold on a fall day in Boston.

Outfit No.2

Although these Sézane boots are some of the most comfortable heels I’ve ever worn, they didn’t last long before I switched back to the loafers. After walking around the Boston Public Gardens in the morning, I realized heels just weren’t going to cut it in Boston (see my tips above). The Gaspard knit was still a great idea though – this time worn with the buttons in the front and in the color camel (the perfect shade for fall!).

Orange silk Ann shirt, black jeans, and loafers to explore Beacon Hill on a warm fall day in Boston.

Outfit No.3

I knew we would be walking a lot around the historic neighborhoods of Beacon Hill and Little Italy, so it was definitely a day for flat shoes. I also looked at the weather ahead of time and saw that it was going to be a bit too warm for a knit. The silk Ann shirt from Sézane was the perfect top for something lightweight yet still autumnal. I liked the idea of mixing the dressier top and blazer with more casual bottoms, but regular blue jeans just didn’t seem to fit the vibe. Instead, I opted for washed black denim, and they worked perfectly for pairing with each outfit on this trip.

Choosing what to wear on your fall trip to Boston should be the fun part of packing! Warm tones, comfy shoes, and some light, cozy layers make the perfect wardrobe for autumn in New England.