Dressing for Fall Events and Festivals in Boston

Dressing for Fall Events and Festivals in Boston

Whether you're attending the Boston Arts Festival, sampling delicious food at the Boston Local Food Festival, or taking in the vibrant colors of the foliage on a nature walk, dressing appropriately will allow you to fully enjoy the experience. By considering the weather, event type, and accessorizing wisely, you'll be able to create a comfortable and fashionable outfit for any fall festival or event in Boston. Let’s look at dressing for these fun outings.

Fall Arts Festivals

Fall arts festivals are one of the best parts of living in (or visiting!) Boston. You can enjoy a jaunt with your friends while you peruse artwork — often with the artist right there to answer any questions that you might have about their creations. Independent artists and creators offer the opportunity to bring beauty into your home while supporting the arts. If you’re more crafty than artistic, no doubt you can find independent artisans who create fun finds, too. Everything from wall art to pottery to jewelry can be found at a fall arts festival. Even if you spend most of your time just looking, it can be a wonderful way to spend a day and learn more about what artists in the area have to offer.

Dressing for a fall arts festival is fun because almost anything goes. You can go super casual in your favorite jeans, women’s T-shirt, and hoodie, or take it up a notch with dark wash jeans, a cute sweater, and a great pair of booties. The outdoor venue allows for much more variety in clothing choices. Be sure to check the weather and bring a women’s fleece jacket or a comfy cardigan to stay warm. Once your fall in Boston is out in force, you might want to bring your winter coat.

Fall Music Festivals

You have to love a fall music festival! Look online to learn more, but Boston has it all. From rock to pop to hip-hop, you will find your favorite musicians performing in and around Boston. Music festivals bring out the whimsy in all of us. Why not wear your favorite graphic T-shirt and jeans, or go for a retro boho style with a flowy women’s blouse, jeans, and booties?

Be sure to stay well hydrated for a fall music festival. Especially if it starts in the day and goes well into the evening, you’ll want to have a good water bottle in your backpack. An extra hoodie that you can use for layering for yourself or a friend is a music festival must-have for fall in Boston.

Fall Football

Of course, what would fall be without football? A crisp fall afternoon is a perfect time to take in a game with your favorite team. Your favorite sweatshirts for women, jeans, and comfy walking shoes are great football choices for starters. Layering a turtleneck under a crewneck sweater can be a great way to stay stylish and add warmth — especially if you can add your favorite team’s colors to your outfit.

The fourth quarter of a football game is almost always chilly, so make sure that you bring outerwear that fits the weather predictions. In addition to a jacket or coat, don’t forget gloves, a hat, and warm boots. For a true Boston day when the mercury is dropping, consider adding a women’s fleece vest under your coat for an extra layer of insulation. If the weather is warmer than you expect, you can carry your coat and stick with the fleece vest over your top. Cheering on your team is always more fun when you are warm and cozy!

Fall Food Trucks

Food trucks are usually just part of a fall festival, but they are a major draw for all of us. Whether you want to support a local restaurant, try a new type of cuisine, or go just for the incredible desserts, you and your friends and family can make an occasion out of enjoying fall food trucks. They offer the ability to indulge in a wide variety of foods all in one place. Why not have everyone in your crew get a different type of cuisine and do a little taste testing from each other’s plates? Be sure to choose a few options that travel well so that you can have delicious leftovers. Taking photos of different types of foods that you find and posting them on social media with you and your friends smiling is fun, too. Food photos are always better with people in them.

You’ll want to wear layers to enjoy fall food trucks. While the sun is out in the afternoon, you may be able to get away with a women’s long sleeve T-shirt and jeans, but all it will take is a brisk breeze or to make a jacket a must-have. A great go-to jacket for fall in Boston is a women’s fleece jacket. They are warm and cozy, come in a wide array of colors, and wash up easily (stains happen).

Layer up and have a wonderful time enjoying the fun festivals that Boston has to offer!


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