When to wear short shorts? Whenever! Short shorts are worn during the summer, winter, spring and fall! Summer Time allows girls to show off their legs while in the winter pair those shorts up with some tights and boots. So many different types of styles.. Embellished, torn up, ironed, ripped, with studs & dyed. Shorts have been around for centuries and have evolved each season. Get a pair and try to create your own look!