well i dont wear jeans very much, barely at all really, only if im going to clubs or bars, and when i do wear jeans, i never ever even consider rolling them up. all of my pants--my jeans, khakis, and cords--had their length tailored after i bought them. the invisible socks sound pretty good, but to be quite honest, my feet never smell and are always clean (pretty much) i clean the inside of my sperrys all the time (takes only 5 mins, just soap + water then air dry) and spray the inside with anti fungal stuff and they dont smell at all.
i agree, im not usually on a boat
i would contest however that the term boatshoes has gone way beyond shoes that are just good for boat/beachwear. i mean look at this pair i picked up 2 days ago (my new favorite pair, but who doesnt like their new shit the most lol)
in my humble opinion at least, these shoes absolutely drip swag, but are also a nice classy look to compliment a pair of beige cords and a darker color top.
i definitely am "that guy" in a sense, but i definitely am not "that guy" who looks like hes going to a beach party, more like that guy who always insists on looking very nice and well put together, regardless of what i am going to do. maybe its bigger in the US (if you are from elsewhere) or maybe its because they are so big amongst members of greek organizations, but where i go to school sperrys are the go to footwear for looking nice at all times, not only do many girls wear them as well, but they seem to love them on guys too