Going from a parochial school with a uniform to a school with a formal dress code. How many dress shirts, blazers, khakis, ties, etc does he need? And for the dumb question of the day, when required to wear a blazer to class, what does one wear over it in the cold, cold winter?
You guys are so helpful and I feel like such a needy idiot. 
There should be a thread somewhere on this topicā¦I seem to remember contributing to one over the past 5 years.
FWIW, to find this, I just typed in BS Wardrobe or some variant. This one deals with a non-formal dress code, but at least gets you in the ballpark for how many of what.
To answer your question about what to wear over a blazerā¦some kids might not wear anything. Others might wear a sweater underneath. Some might layer a down vest overā¦others might wear a ski jacket. An insulated barn coat or Barbour (with liner) works too.
However, if it was me, Iād wear a wool (or other similar fabric) overcoatā¦I have both long and ābarn coatā length options.
Thanks! I was searching dress codeā¦wardrobe never occurred to me.
Try this link instead:
http://talk.collegeconfidential.com/prep-school-parents/1329110-realistic-amount-of-clothing-p1.html
Just to make sure you read the first page (which has a few lists from a few parents).
For formal dress we stuck with the basics ( navy blazers, khakis, oxford cloth button down shirts ) and the guys put their personal stamp on their ties (regular and bow ) and belts. For winter they layered up with a quarter zip over their shirt and tie and rarely wore a jacket over their blazer. Although last winter was pretty brutalā¦
My kids have worn all kinds off outerwear but last year K2 favored a thin Patagonia puff jacket.
If your son will be boarding- donāt overbuy ( even though youāll be tempted to! ) . Boys typically wear the same pair of pants for a week when they have seven clean pairs hanging in their closet. They seem to get by with very littleā¦ 
For winter, some boys wear parkas or barn coats over Blazers. Pea-coats are very popular at my sonās school. Also, check and see if winter dress code is the same as fall and spring. At his school, during fall and spring, the dress code is button down shirt, tie, blazer, shorts or long pants (no cargo pants or jeans). In winter, you can wear a turtleneck with your blazer-- or a button down shirt, tie, and sweater-- without the blazer. Thatās to make it easier to wear whatever winter coat you like. Shoes in fall and spring are usually top siders, flip flops, or running shoes. Winter shoes are usually Tims (work boots).
I suggest that before you buy anything, to sign up to receive emails from stores (for me, macys, polo outlet, etc) to notify you for friends and family type sales (Iāve saved a lot of money that it is really worth getting hit with a bunch of emails).
I suggest:
2-3 blazers (at least one navy)
6-12 button down shirts (no-iron from landās end have been great)
6-12 pants
1-2 golf shirts and 1-2 khaki shorts for academic casual days
dress socks, leather belt and leather shoes (most kids wear sperry-type boat shoes)
1-2 sweaters (3/4 zip are popular) and 1-2 turtlenecks. Kids can wear turtlenecks in place of tie & dress shirt in the winter.
Hill will modify the dress code on really cold days and ārequireā sweaters or turtlenecks. And the kids wear their winter jackets instead of blazers on those days.
Also, during winter term boys can wear boots- ll bean boots and timberlands are most popular. My kids wear their ski jackets over their blazers. Some kids have pea coats and barn jackets too. My kids also have long underwear that they wear to keep warmā¦ā¦ the wind can be brutal during the winter in Pottstown.
Happy shopping!!! Iām sure you know that there are outlets near Hill!