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21 Autumnal Gap and Old Navy Pieces That Look Like They Belong on a New England Leaf-Peeping Trip

By Swedan Margen

21 Autumnal Gap and Old Navy Pieces That Look Like They Belong on a New England Leaf-Peeping Trip

I love nothing more than dressing for a theme. Give me an aesthetic to align my wardrobe with, and I'm a happy camper (unless you're actually taking me camping because that's not my vibe). When the calendar flips to November and the leaves start to crisp and curl, I instantly want to dress like I live in a Nancy Meyers version of New England. Think cozy knits, perfectly worn denim, and layers that look like they were made for apple picking, leaf peeping, and bookstore browsing.

That's exactly the energy behind my shopping selections for this story. From Fair Isle sweaters and barn jackets to clogs and corduroy pants, these Gap and Old Navy items channel peak fall nostalgia without veering into costume territory. Whether you're actually headed to Vermont or just craving that cinnamon-scented aesthetic, these pieces will get you there—no plane ticket (or tent) required.

Water-Resistant Long Barn Coat

Old Navy

Water-Resistant Long Barn Coat

This sale price is too good to pass up.

Sosoft Cropped Mock-Neck Cable Sweater

Old Navy

SoSoft Cropped Mock-Neck Cable Sweater

It's giving When Harry Met Sally.

Waxed Canvas Barn Jacket

Gap

Waxed Canvas Barn Jacket

It's not fall without a barn jacket.

Sosoft Mock-Neck Fair Isle Sweater

Old Navy

SoSoft Mock-Neck Fair Isle Sweater

You'll be the chicest person at the ski lodge in this cute sweater.

100% Cotton Oversized Sweater

Gap

100% Cotton Oversized Sweater

I own this 100% cotton sweater in two different colors, and I can't recommend it enough.

High Rise Stride Corduroy Wide-Leg Pants

Gap

High Rise Stride Corduroy Wide-Leg Pants

These leopard pants are so fun.

Fair Isle Crew Socks 2-Pack for Women

Old Navy

Fair Isle Crew Socks

Wear these with your favorite loafers.

Canvas Barn Jacket

Old Navy

Canvas Barn Jacket

This contrasting collar is such a chic touch.

Mayfair Clog

Clogs are cozy and chic—the perfect combination.

Sosoft Cropped Fair Isle Cardigan Sweater

Old Navy

SoSoft Cropped Fair Isle Cardigan Sweater

Fair Isle sweaters will never go out of style.

Gap 365 High Rise Brushed Twill Pleated Trousers

Gap

365 High Rise Brushed Twill Pleated Trousers

These trousers are so posh.

Chelsea Boots for Women

This $31 price tag is hard to beat.

Old Navy X Anna Sui Tiered Midi Skirt

Old Navy x Anna Sui

Tiered Midi Skirt

Cinched-Waist Twill Utility Jacket

Old Navy

Cinched-Waist Twill Utility Jacket

This jacket is as practical as it is stylish.

Waxed Barn Jacket
Mid Rise Ultrasoft Baggy Jeans

Gap

Mid Rise Ultrasoft Baggy Jeans

These jeans have such good reviews.

Low-Heel Booties for Women

Old Navy

Low-Heel Booties

The kind of shoes you can wear with anything and everything.

Old Navy X Anna Sui Vegan Leather Coat

Old Navy x Anna Sui

Vegan Leather Coat

This collab was a match made in fashion heaven.

Wool-Blend Wrap Coat
Oversized Wool-Blend Blazer

Gap

Oversized Wool-Blend Blazer

Modern Crewneck T-Shirt

Gap

Modern Crewneck T-Shirt

A great foundational piece for layering.

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