What to Wear for a Girls’ Weekend Upstate

Nothing says reset like a girls’ weekend in the Hudson Valley or Berkshires—think winding roads, boutique inns, and endless laughs. But what should you wear when your itinerary includes everything from wine tastings to nature walks to late-night bonfires?

Your packing list should blend comfort with cool. Think cozy, effortless, and chic. Here’s how to make the most of your weekend wardrobe:

Friday: Travel & Wine Tasting

Start strong with comfortable jeans or soft wide-leg pants, paired with a relaxed blouse or knit. Add a layer like a cropped jacket or cardigan and slip-on shoes that work for walking and sipping.

Saturday Morning: Market & Meandering

A soft midi dress or flowy skirt with a denim jacket and sneakers is ideal for exploring local markets or antique shops. Keep accessories simple and functional—crossbody bags, sunglasses, and delicate jewelry.

Saturday Night: Dinner & Games

Swap into a lightweight sweater dress or chic lounge set. Elevate the look with gold hoops, a leather clutch, and a bit of blush. It’s casual, but intentional.

Sunday: Nature & Brunch

Leggings, an oversized knit, and a baseball cap make the perfect cozy combo for a morning hike or casual brunch. Add a trench or puff vest depending on the weather.

Essentials to Pack:

• One great dress you can style up or down

• A knit set or lounge outfit

• Layering pieces (cardigans, shackets, vests)

• Stylish sneakers + one elevated shoe option

A girls’ weekend is all about ease and connection—your wardrobe should feel the same. Aim for practical pieces with personality so you feel like yourself in every setting.