Threads about cowboy boots always seem to bring out peoples strong opinions. People rarely seem to be neutral with their thoughts about wearing cowboy boots.
Although I don't live in the South West and don't ride a horse or do any ranching, I have been proudly wearing my 30+ pairs of cowboy boots for the past 27 years and will continue to do so no matter what other's opinions of them are.
I have always admired the quote, "Pity be those who look to others for permission for their own pleasure."
People's negativity toward cowboy boots usually falls into one of two catagories. Some people don't like the look, and others find they just hurt their feet.
The people in the first catagory are usually not aware of all the different possibilties there are for designing cowboy boots. The first image the average person usually thinks of is a very pointy boot with a high underslung heel. One usually doesn't think about a very elegant boot with a classy square tapered French Toe, a lower, slighty tapered heel, and a rich chocolate brown or black French Calf or kangaroo leather with a nice highly polished finish. I have no problem wearing this sort of boot with a suit, or blazer to even the most dressy of occasions. Of course I like the other styles of boots also with jeans and other casual dress.
As far as the comfort factor goes, a well fitted boot will be your best friend, and a poorly fitted boot will be your worst nightmare. I heard a statistic that perhaps as many as 80% of boot wearers out there don't have properly fitting boots. I wouldn't be surprised if this is true for men's dress shoes also. Getting a proper fit is not an easy task, and for some like me, it is impossible without having them custom made. I have had boots made by most of the well known boot companies in El Paso, and elsewhere in Texas and Arizona. My favorite bootmaker is now in his 80's and has made boots for President Eisenhower. He has made me 10 pairs of boots during the past year, and they are the best fitting, best looking boots I have ever worn. Plus, I get a tremendous amount of pride and satisfaction knowing that I am wearing boots I designed myself, and each pair is one of a kind.
If anyone has any specific questions about cowboy boots, (either custom made or factory boots) please feel free to send me a personal message.