What to Wear for a Vermont Fall Weekend
What to Wear for a Vermont Fall Weekend
📍 Basin Harbor, Vermont
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If there’s one thing I love almost as much as a fall weekend in New England, it’s packing for one. Give me colorful foliage, historic inns, a cozy cottage, and an excuse to break out my favorite sweaters, and I’m a happy camper. Of course, dressing for Vermont in the Fall can be a little tricky. Between chilly mornings, warmer afternoons, and plenty of time spent outdoors, I always try to pack pieces that are comfortable, easy to layer, and still feel put together. For any fall trip to the Green Mountain State, I lean into classic New England style with lots of navy, chocolate brown, denim, and a few playful touches. Here’s everything to wear throughout your stay, from exploring the charming small towns to enjoying a quiet morning at your hotel.
Shirt || Jeans || Similar Loafers || Handbag || Hat
A Little Madras for a Fall Afternoon
I know plaid is practically a requirement for fall in New England, but I wanted to have a little fun with it. This colorful madras-inspired button-down felt like a nice change from the darker colors I typically gravitate toward this time of year. I paired it with white cropped trousers, brown suede loafers, and a chocolate brown baseball cap for a casual afternoon exploring. I also brought along my navy Louis Vuitton bag, which picked up the blue in the shirt. While white pants might not be the first thing that comes to mind for October in Vermont, I love wearing them well beyond Labor Day, especially with rich brown accessories.
Sweater || Shirt || Pants || Boots || Handbag
Navy on Navy for a Cozy Morning
You can never go wrong with navy, particularly in New England. For one of our mornings at Basin Harbor, I layered a chunky navy sweater over a crisp white button-down and paired it with navy wide-leg trousers. The little bit of white peeking out at the collar, cuffs, and hem helped break up the monochromatic look, while brown suede ankle boots and a woven tote kept it from feeling too formal. I love an outfit like this for a leisurely breakfast, wandering around the resort, or stopping for coffee before heading out for the day. It’s comfortable enough for a relaxed weekend but still feels polished.
Jacket || Sweater || Jeans || Boots
A Barn Jacket by Lake Champlain
If I had to pick one piece that perfectly captures fall in New England, it might be a classic barn jacket. I wore mine over a cream sweater with a red American flag motif, dark-wash wide-leg jeans, and brown suede boots for an afternoon by Lake Champlain. The olive jacket was especially practical for the cooler lakeside weather, and I love how the little pop of red made an otherwise neutral outfit feel more playful. This was exactly the kind of look I wanted for a family weekend at Basin Harbor: comfortable enough for outdoor activities, warm enough for a breezy afternoon, and classic enough that I’ll happily wear it for years.
Similar Dress || Similar Boots || Similar Handbag
A Sweater Dress for Dinner
I always like to pack at least one outfit that feels a little dressier, even for a casual weekend away. This camel ribbed sweater dress was an easy choice because it’s comfortable, warm, and requires very little styling. I paired it with cognac suede knee-high boots and a structured chocolate brown handbag for a simple, tonal look. I particularly love wearing sweater dresses in the fall because they feel just as cozy as a favorite knit but are a little more polished for dinner or an evening out. This is also the kind of outfit I’d happily repeat for a fall date night at home.
Sweater || Button-Down || Jeans || Boots || Similar Handbag
Chocolate Brown and a Classic Button-Down
I’ve been reaching for chocolate brown constantly this fall, and this chunky cable-knit cardigan has quickly become one of my favorite pieces. For a relaxed afternoon, I wore it over a light blue button-down with cream wide-leg trousers, brown suede ankle boots, and my structured brown handbag. I love how the blue shirt brightens up the darker cardigan, while the cream trousers keep everything feeling fresh. This is the sort of outfit that works particularly well for a New England getaway because it’s easy to adjust throughout the day. Wear the cardigan buttoned when it’s chilly, or leave it open when the afternoon warms up.
Striped Pajamas and a View of the Lake
I’m a firm believer that pajamas deserve a spot on the packing list, especially when you’re staying somewhere as cozy as Basin Harbor. For our weekend, I brought along a red-and-white striped pajama set that felt perfectly appropriate for a fall morning in Vermont. One of my favorite parts of our cottage was the view overlooking Lake Champlain, and I loved being able to step outside with a cup of coffee and enjoy it before the day got started. It was such a peaceful way to begin the morning, and a reminder that some of the best parts of a weekend away happen before you’ve even gotten dressed.
Sweater || Jeans || Sneakers || Handbag || Sunglasses
Looking back at everything I wore, I think my favorite thing about packing for Vermont is how naturally my everyday wardrobe fits the setting. Classic sweaters, good denim, comfortable boots, and a few thoughtful accessories are really all you need. I also love that so many of these pieces can be mixed and matched, which makes packing for a short getaway much easier. Our weekend at Basin Harbor was filled with beautiful foliage, time outdoors, and plenty of family fun, and I’m already looking forward to another visit. Until then, I’ll be taking every opportunity to wear these cozy New England-inspired outfits throughout the rest of fall.
Love from Vermont,
Katie
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