<p>DoctorDerrin, I empathize completely. We live on the equator and our son is in the Berkshires. Some days the temperature difference is over 100 degrees F!</p>
<p>Whether your son stocks up on winterwear now or later depends on where he's going to be next year. If he's going to be in or near a city, he'll have some options. If he's headed for the boonies ala Williams, Middlebury, then I'd buy now. As Driver said above, the cold comes on early and wickedly. Like many boys my son wouldn't have had the motivation or knowledge to buy for himself, so before dropping him off we spent a few days in New York stocking up on winterwear.</p>
<p>The other thing is that the retail cycle is wierd (don't ask).When it starts really getting cold, the stores the stores are closing out their winter clothes and stocking up on Spring. August is the right time to buy if you want to find a selection of sizes and colors.</p>
<p>I second the Northface idea, even though very expensive, their multi-layer polyfill zip together jackets are both cool and very functional. They can be worn for years. I agree with the parent who said that LLBean and Lands' End may not be popular on campus. </p>
<p>The next most important item is a pair of waterproof snow boots.
There are lots of styles of boots, so this is a more subjective buy. Both the coat and boots can feel pretty strange to a warmweather kid who's used to flipflops and cutoffs, so be prepared for some complaining.</p>
<p>He'll also need gloves, hats, scarves, socks and layering pieces. 100% polyester fleece is wonderful. It's light and warm and can be found in all price ranges, no need to go for the branded "Polar" stuff. All the on-line catalogs carry tons of fleece items.</p>
<p>I'd also suggest some thermal underwear. Silk is very warm, but synthetic is easier to care for.</p>
<p>If you can secure the coat and boots in advance he can supplement the rest on line or locally. Now for you when you visit. . .</p>