Wearing pants shorter....How short ?

I visited the tailor recently and had him hem some w+h roped pants. He had measured it for a slight break but I asked him to bring it up an additional two inches. So right at the ankle

I stack or roll em, hemmed jeans look awful.

2 inches could look fine or bad depending so post pic if you want substantive input.

I really don't dig that style, makes most people look less like badasses like squares to me but to each his own.

I like the look, but I feel like it makes me look like I am trying to hard

LOL @ 'squares'. Wearing strides clear of the shoes looks a damn sight sharper than having them dragging on the deck. Late 1960s mods and skinheads from the UK would disagree with you all the way, and there were never a sharper, less 'square' set of dressers, in their own way. Strides hang better when they don't catch on shoes.

Well said,M-o-M