What I Pack for a Weekend in the Woods

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Fall is my favoritest time in New York City. Actually to be more accurate, it’s my favoritest time just outside of New York City. I love nothing more than a weekend upstate or in the Berkshires, and have bookmarked dozens of destinations to hit up this season and next: Scribner’s Lodge, Audrey’s Farmhouse, The Debruce just to name a few… But even when I’m just visiting a friend’s country cottage in Rhinebeck, I like to bring a little city style with me. Here are the 5 essentials I always pack for an autumnal weekend in the woods.

Combat Booties

Nothing makes you feel instantly cool better than a great pair of booties. I love a combat boot that looks as great on a hike as it does at the farmer’s market. Great with leggings and flannel, jeans or even a prairie dress. Look for a streamlined version rather than a massive Doc Marten and you’ll fit right in with the rest of the NYC expats.

Boyfriend Jeans

The perfect pair of distressed, high-waisted, relaxed-fit denim is perfectly hip and yet perfectly casual. Great with a cropped sweater, a tucked in tee, or a turtleneck - these may be the only pants you need all weekend.

Shearling Jacket

Top off any casual outfit with a super cool jacket that’s both snuggly and a little lux, and you’re good to go. Getting apple cider at the local farmer’s market never looked so cozy…

Felted Hat

A hat makes everything look better. Period. Think of it like the cherry-on-top of any outfit - making even a boring sweater and jeans look suddenly un-boring!

Statement Sunnies

Again, accessories are everything. Grab a cool pair of shades to cover your makeup-free, drank too much artisanal-local-beer-last-night face and you’ll be covered. Literally and figuratively.


LMNT Sunglasses $30

Celine Tortoise Mix Sunglasses $319

Celine Black Sunglasses $199

Rebecca Minkoff Leopard Bootie SALE $186

Vince Cabria Combat Boot $395

Levi’s Sherpa Jacket w/ Removable Fur Collar $168

Albertus Swanepol Felted Hat $320

Rag & Bone Felted Hat

Vintage Levi’s Mom Jeans $65 and up