My 27 year old son diagnosed paranoid schizophrenic will wear long sleeved shirts or sweatshirts, long pants in the summer and then in the winter he wears shorts and tees! I don't have a boy, but my 2 1/2 year old daughter won't wear a shirt to bed. I used to put her in full pj's, then went down to just a shirt for the summer, but partway through this. How to dress in summers for teenage boys. Wear light materials like cotton, this is will keep you off from feeling hot and sweaty all the time. 6 things you should know about teenage boys. They will see those girl parts. Even though i have been getting dressed in the dark, in the closet or in the bathroom for years,. Well i don't think boys don't wear sleeveless tops. Some of them do definitely.