I have 3 pairs of Ariats, 2 pairs of Rockys, 2 pairs of DoubleH, 2 pairs of Durango Rebels, and 1 pair of Corrals. (Yes I'm worse than a woman with boots, but they're pretty much the only type of shoes I put on my feet.) Luckily we have an awesome store here that sells close out and factory defect, and also used shoes. That's where most of my boots come from. I've never paid more that $90 for a pair of boots there and they were in like new condition.
Some of those are work boots, some are nicer boots. I just throw a pair on based on my mood and what I'm wearing. If I ranked them in comfort it would be Ariat, Durango, Double H, Rocky, and then Corral. It's so close it's hard to pick though.
At work we're not allowed to wear slip on boots because some idiot twisted their ankle in slip on boots 20 years ago and my company is the king of "blanket" safety policies. They provide our boots though and I usually get 2 pair per year. I go back and forth between Timberland Pros and Keens. The Timberlands are a little more comfortable, but the soles don't hold up as good. My last pair the sole split all the way across right under the balls of my feet. A lot of that may have to do with the fact that I work in a chemical plant. Stuff just deteriorates the soles.