These are musings reflecting opinions of a guy who wears cowboy boots regularly.
1. Wear what you like and what fits you and your lifestyle.
2. Stand tall and proudly.
3. Smile! Men appear more confident and self-assured when they smile (and wear boots!)
4. Stop obsessing about what other people may say or think about you wearing cowboy boots. Seriously, get over it. If you're worried that someone may say something because wearing boots is new to you or not common where you live, then make the choice not to wear them. But it is YOUR choice – not someone else's.
5. If you have nice boots that you want to show, tuck your jeans into them. If you don't want to do that, then don't. It's your choice.
6. Cowboy boots go well with dress clothes or a suit. Generally, it is wise to choose an all-leather boot or subtle alternate skin boots (such as smooth ostrich or Teju lizard) in black, brown, or black cherry and which have a rounded or semi-rounded toe and traditional heel height. Boots with more fanciful design, sharp X-toes, high heels, or made of unusual materials (Caiman alligator, rattlesnake, python, etc.) may be too ostentatious to wear to places where one might wear a suit, such as at an office, conference, wedding, funeral, or to a place of worship.
7. Have at least two, if not more, pairs of cowboy boots if you will be wearing them regularly. It is a good idea to let boots “breathe” for at least one day between wearing them. The boots need to air out and allow time for sweat which may have been absorbed into the leather and insole to evaporate. (This is also sometimes called “rotating boots” but does not mean turning them around.)
8. Do not wear cowboy boots that have smooth leather soles while operating a motorcycle. This is a safety precaution – smooth soles provide no traction! Same applies about wearing smooth-soled cowboy boots in places that may be slick with rain, snow or ice.
9. Take care of your boots, and they'll take care of you.