I have switched from conventional dress shoes to western boots. I must have around 10 pair of Lucchese, Heritage, and other brands, but the Lucchese and Heritage are my favorites. I find them more fashionable and stylish and much more comfortable to wear. Do they raise some eyebrows? Maybe a few, but I've gotten a lot more compliments on them.
I like westerns but not to have to stand in most of the day as I have to when working. I also have a very narrow foot so finding off the shelf boots to fit is just about impossible. I do have three pair of custom made, the first in sharkskin , about 25 years old, made in the SAS (ladies shoes) custom bootmaking shop which no longer exists. I had another pair made of the same material a few year later but they were too tight and had sent them back. A contractor was on the roof doing some kind of heating/airconditing work and set something on fire which got out of control. Needless to say my boots went up in the blaze.
I contacted the gentleman who ran that shop and he remembered and did not know what the company was going to do about that operation and advised me to wait a month or so. They decided not to resume production. He asked what I paid for them and based on my report sent me a refund check. A year or so later he went independent, and when my son graduated from UT in Austin, we ran down to San Antonio and had a pair made for each of us in alligator, and I got one more pair a few years later, my newest pair being about 15 years old and still look like new.