[I tried to title this “Boots” but Waldo says it has to be 8 characters long]
I have a few pair, mostly work, some of the works can get polished enough to be presentable in social situations (Ariat/Redwing). I have a couple of pair of “fancy boots” that are frankly not that comfortable at all, so I need new fancy boots. Comfort is more important than cost, but I’m not interested in a thousand dollar pair of boots.
Since we’re referencing boots, llamas and Limey…”Tony Lama” is the boot maker. Tony Llama worked on Monty Python and the Holy Grail, and was presumably sacked, along with those who are responsible for sacking everyone previously sacked. At great expense and at the last minute.
I had some custom made in SA from water buffalo and customized the uppers with pull holes. They were $600, but I’ll never have to buy another pair. They measure everything and the fit is perfect. You can pick the heel you want and the material for the sole as well. Problem is, the was 17 years ago and I’m sure $600 won’t cut it anymore.
Tony Lama is now just a brand name, manufactured by Justin, owned by Berkshire Hathaway. I don’t know if that’s horrible, but it’s been a common tale for long standing American brands. Very few can survive the “venture capitalists”.
I have seen a lot of chatter about Thursday Boots. I don’t know if they’re any good or not though.
If you’re looking for dress boots, there’s always the old standby brands such as Allen Edmonds. I would also look to some brands in the UK. I have a pair from Herring (shoes, not boots though they have lots of dress boots), that are very comfortable and extremely well made. There’s also companies like Trickers or Crockett & Jones, but then you’re getting up into the $800 or so territory. They’ll last you the rest of your life, but they ain’t cheap.
I want to get me a nice pair of Beatle Boots and start wearing them before all the suffering college kids make them a “new” fad. Like my Joy Division T-shirt…
Were it me, for a pair that I don’t wear that often and will last me the rest of my life, I’d go the custom route, but it would probably exceed your desired budget. Have you looked at Tecovas? I hear good things about them too, but have never owned a pair. My most comfortable pair are Ariat, though they are certainly not the polishing up kind.