I got the niece and nephew gift cards to LL Bean when they went to school in NH and VT, they used them up before December. We found North Face had a good sale in early summer. Also, keep in mind that some buildings (like performing arts) may ask students to take off snow boots in the front hallway… They complained more about “Slush” season than snow! So consider water proof boots and/or Hunters, Sorel, or LL Bean duck boots that can withstand the slush, rain, mud
There are some decent sales going on now for outerwear- I favor down for superior lightweight warmth. Check out REI, REI Garage and EMS. Macy’s too. Regarding socks- wool or wool blend socks are great. The best wool socks are hand knit ones, if one has the ability and inclination- unsurpassed fit.
@carpoolingma - this thread is making me hyperventilate. Lizardkid wouldn’t know a name brand if it fell on him. He’s pretty happy with Target and although he doesn’t know it, half his clothes come from Children’s Place. And since he doesn’t fit into adult sizes yet (except for t-shirts), we are pretty limited.
The good news? The vast majority of stuff you’ll need for next year is on sale now.
FWIW- Orvis has some nice Barbour outerwear on sale right now…
North Face is having a barn burner sale, too…
@vwlizard A lot can change between 7th and the beginning of 9th. CPKid didn’t know brand names either except for athletic wear (Underarmor, Nike) even with an older, somewhat brand conscious sister. In preparation for boarding school, I bought CPKid some (on sale) Vineyard Vines. The funny thing is that CPKid refuses to wear it - he says it says something about him that is just not his scene. The one brand I recommend depending on how your DS grows is Topman (at Nordstrom) if you need a sports jacket or a suit with a slighter cut. DS started in kids but then grew and was too tall/had arms that were too long for kids sizes but too string-beany at first for regular mens sizes.
And then there are kids who just detest shopping. When I have to take DS shopping (due to extreme growth and having to try things on once in a while), we can manage one store for regular (dress code) clothes and one for outerwear. Pretty much all his outerwear is LL Bean (and I’m counting on the boots and jacket from this year lasting a while) and his pants and ties are J Crew. His dress shirts are all Lands End wrinkle free, which I can order. For smaller boys, Kohl’s has good deals on blue blazers in boys’ sizes (we have every size from the past few years; CTKid2 is growing into them). My freshman MAY be able to identify Vineyard Vines as a brand and probably has no idea where we buy his clothes. He is brand-clueless.
“I bought CPKid some (on sale) Vineyard Vines. The funny thing is that CPKid refuses to wear it - he says it says something about him that is just not his scene.”
I can understand a student feeling that way. Some kids wear certain brands like a uniform not dissimilar in some ways to gang colors. 
A few things I’ve learned from experience:
You can buy early and think you got a great deal on stuff for the next season and then your kiddo goes through a growth spurt and your bargain shopping is no longer a good fit.
Your kid who could care less about fashion might suddenly start caring very much about what he/she wears and how it defines them.