ok, native texan checking in --
i own a pair of cowboy boots, that i had way before the trend. they are a plain pair of justin roper boots (less pointy and the heel doesn't slope on the back) that are all beatup and nasty -- they look awesome. it all depends on what you wear with them. yeah, i probably would look like a hillbilly if i wore em with wranglers and a western shirt but i dont. i usually wear em with straight leg jeans or bootcut jeans with very slight flare because the bigger the flare the smaller my feet look lol, i hate when they get all covered up and all u can see is a point. reminds of the whole pointy high heel and jeans look for women (i think it looks hot on girls though).
i think they key to wearing boots is loooking like ur not trying. like if i'm going to wear boots i'm going to where real cowboy boots, not wannabe ones by kenneth cole or DG. the more beatup they look, the better in my opinion. and dont wear them with cowboy stuff top to bottom, oh god.
if your not bold enough for real cowboy boots, i think frye campus boots are a nice compromise. still get the ruggedness but a rounder toe. plus they look really aweseom when there all beatup too. i just bought a vintage pair of tan ones.
