Some people look good in bolo ties. Â My Grandfather wore bolo ties and looked great wearing them. Â However, my Grandfather was a genuine, working cowboy, who lived on a ranch, rode horses, and went to the cattle auction and bid on steers and heiffers with other cowboys who wore bolo ties. Â If you aren't a real cowboy, I don't know if you really should wear a bolo tie. Â You will probably look like a poseur moron. (Like the guys who wear their jeans tucked into their cowboy boots.) For those who are thinking "Hey, I rode the pony that one time at summer camp, and didn't even fall off. Maybe I'm a real cowboy and could wear a bolo tie." If you haven't roped, branded, and cut the nuts off a bull calf, you probably aren't a real cowboy, summer camp notwithstanding.