Whether you’re traveling to Vermont for an adventure filled weekend or headed to Connecticut for a cozy few days cuddled by the fire – here are my must-haves for classic, comfy style for fall and winter getaways. 

Tops

A Neutral Cozy Sweater  — Maje, Joie, Reiss, and Sandro always have lovely options.

A Comfy Fitted Sweatshirt  —  you can never go wrong with Lululemon‘s Scuba Hoodie.

Bottoms 

Fitted Cargo Pants —  Joie makes the most flattering cargo pant you’ve ever seen. They go with everything and are the perfect mix of casual and sexy.

Well-designed Yoga Pants —  if you’re hiking, exploring, or doing any kind of fun outdoor activity, jeans and regular pants just won’t do. Again, Lululemon has the best options.

Boots 

Riding Boot — Frye has been my go-to for years for riding boots. They last forever, you can dress them up or down, and they fit like a glove.

Hiking and Snow Boots — Always Sorel. They are the warmest and chicest. Their price point is incredible given their durability, comfort, and sophisticated style.

Jackets/Coats

Lightweight Jackets — I just discovered SAM last fall and was amazed at how lightweight their jackets are and still so warm. My favorite is their Heavy Freestyle Down Jacket.

Heavier Coats – I’ve been wearing Mackage for years as they make some of the warmest jackets and coats you’ll ever wear and they are standout pieces. All Saints is always the steady when you want to dress things up a bit.

Accessories 

Hands — Nirvanna Designs makes handwarmers in lots of colors that keep your hands cozy while still leaving your fingers free for the phone. 

Hats — TurtleFur hats are the perfect combo of chic, durability, and warmth.