We always recommend packing and wearing layers during a trip to the Berkshires. Depending on your activity, you may move from one temperature to another fairly quickly. The winter months can be very cold, so we definitely recommend bringing your winter weather gear.
The Berkshires, with its many trendy restaurants and cultural attractions, is an extremely welcoming locale. You’ll see people wearing a range of informal and formal outfits, but you should fit right in dressing casually almost everywhere you go.
If you’re looking to do some shopping while you’re in the area, check out the Lee Premium Outlets. Or for more seasonal gear, check out Arcadian Shop in Lenox, Barrington Outfitters in Great Barrington, or Westerlind in Great Barrington.