There is nothing quite like fall in New England.
The leaves are changing, the air finally has that crisp feeling, and suddenly every weekend has somewhere to go—apple picking, farmers markets, Oktoberfest, pumpkin patches and drives to see the foliage.
And, of course, the question becomes: what are we wearing?
Having spent so many falls in New England, I know the formula. You want layers, great denim, comfortable shoes and pieces that feel fall without looking like you dressed specifically for the pumpkin patch.
I pulled together my favorite pieces for all the best New England fall happenings.
Fall Foliage 🍁
WHAT I’D WEAR: A GREAT JACKET + DENIM + BOOTS
Whether you're heading out for a foliage drive, walking through a small Vermont town or stopping somewhere for lunch, this is where a really good fall jacket earns its place in your closet.
I'm loving the Barbour Classic Mary Wax Jacket for that quintessential New England look. The Marine Layer Riley Barn Jacket is another great option, while the Pilcro Rumi Faux Leather Moto Jacket gives the outfit a little more edge.
Add relaxed denim—I love the Citizens of Humanity Miro or MOTHER Mid Rise Lasso Sneak—and finish with a waterproof Chelsea boot.
THE LOOK: Barn jacket + relaxed denim + Chelsea boot + great sunglasses.
Dear Lucy tip: Don't save your sunglasses for summer. A great tortoise pair with fall layers is one of my favorite combinations.
Apple Picking 🍎
WHAT I’D WEAR: THE COZY SWEATER + JEANS + UGG®
This is where the sweater comes out.
The THE GREAT. Nordic Lodge Cardigan has exactly the nostalgic New England feeling I want for an October afternoon. The Z SUPPLY Medina Argyle Cardigan is another great choice if you want something a little more classic.
Add relaxed denim and the Sorel Daystorm Waterproof Chelsea Boot
Comfortable enough to walk around an orchard, but still cute enough for the inevitable apple-picking photos.
THE LOOK: Fair Isle or argyle knit + relaxed jeans + chunky boot.
COZY. EASY. VERY OCTOBER. 🍎
Farmers Market 🥐☕️
WHAT I’D WEAR: EASY LAYERS + GOOD DENIM
Farmers-market dressing should look like you didn't try too hard.
Start with the Faherty Sunwashed Long-Sleeve Retro Tee or Faherty Featherweight Freestyle Layering Tee, add denim and throw on a barn jacket.
The Marine Layer Riley Denim Barn Jacket is especially good here because denim-on-denim feels very right again.
Add a silk bandana, sunglasses and a comfortable shoe and you're done.
THE LOOK: Layering tee + denim + barn jacket + bandana.
It's the outfit that works for the farmers market at 10 and lunch at 12.
Oktoberfest 🍺
WHAT I’D WEAR: A GREAT KNIT + DENIM + BOOTS
No theme dressing required.
I'd take the cozy fall feeling and make it a little more polished.
The Pilcro Goose Cotton-Wool Blend Cardigan is perfect because it's fun without feeling costume-y. Or go classic with the Quince Mongolian Cashmere Crewneck and add a scarf or bandana for color.
Finish with relaxed denim and the UGG® Classic Ultra Mini.
THE LOOK: Interesting sweater + jeans + UGG® Classic Ultra Mini + fall accessory.
And yes, waterproof shoes are a very good idea when you're spending an October afternoon outside.
Pumpkin Patch 🎃
WHAT I’D WEAR: TEXTURE + LAYERS + A PRACTICAL SHOE
This is where I'd have a little fun with fall.
Try the Saylor Alaska Jacket with denim, or layer the Marine Layer Riley Barn Jacket over a sweater or tee.
And if the ground is muddy—which, let's be real, it probably is—this is exactly where the Hunter Play Short Rain Boot comes in.
Add the Madewell silk bandana for a little color without turning the outfit into a fall costume.
THE LOOK: Cozy jacket + denim + Hunter boots + bandana.
PUMPKIN PATCH, BUT MAKE IT GOOD. 🎃
The New England Fall Formula
The nice thing about all of these outfits is that you really don't need five separate wardrobes for five different weekend plans.
Start with a few great pieces:
Relaxed denim. A cozy knit. A barn or wax jacket. A weather-friendly boot. A great layering tee. And one or two accessories that make everything feel finished.
Mix them differently depending on where you're headed.
That's the way I've always liked to shop—and exactly how I think a fall wardrobe should work.
Because the best fall pieces aren't the ones you wear once for the photo.
They're the ones you keep reaching for every single weekend.
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