t depends a lot on the “look” you are trying to achieve.
High tops are very popular, especially now since skinny jeans has become unfashionable, and the move is going towards baggy and long.
Do not wear them with shorts, especially not gym shorts - the look is terrible!
The most popular way to wear high tops is with full length jeans, regular or baggy fit, but if you wear low cut socks, you can easily wear high tops with 3/4 jeans and the look will be very good.
Always wear the tongue of the high tops in front of your jeans (so tuck the jeans behind the tongue). Its also very popular to loose lace them, and if they have a velcro strap, to wear that unstrapped, to the side.
Lately, its also very fashionable to have 2 laces of different colour in each sneaker with the lace ends sticking out about 2 inches from each hole. The most popular brands are the thicker puffier Nikes, Adidas, Osiris, DC’s, Ewings etc. These are well made, good quality and very supportive high tops. Definitely not the thinner styles like Converse that offer no support, are very thin and fall apart easily.