I have square toed boots. Ariats with blue stitching. I absolutely HATE pointy toed boots, I think they look absolutely silly (I'm not an elf, thanks) and I really wish I had a pair of round toed... But, I'm really picky about my boots because prior to owning a horse I could never imagine myself wearing cowboy boots. I like them black, with minimal design (if any) and no pointy toes, and it works awesome for me. The only reason I REALLY wanted a pair was A) no tread for safer riding in stirrups and B) I could just slide them on. When you live in a dorm and have to put on and take off shoes multiple times per day that was AWESOME.
Aaaand now they're so comfy I wear them as my normal footwear except in the winter. As for clothing, I just go out in whatever clothed I happen to have on that day!