I’m a bit of a boot hoarder, and after years in a variety of brands (Vogel, Sergio Grasso, and others) I’ve ended up with an assortment of Ariat boots as they’ve come out with so many nice models.
I was a die hard half chap person and rode in my half chaps daily until the comfy boots (like the Ariat Volants) came out. I’ve since made the transition to riding in tall boots every day.
I’m not going to dig up pictures right now, but I’ve posted pictures of all of the boots below in past boot threads if you want to see what they look like IRL.
Ariat V Sports - these are my daily riding boots and are super comfortable and fit beautifully. Not quite as nice as my other Ariats, but with the $285 (IIRC) price tag, far better quality and fit than I expected. Downside is that the blue cuff may not be the right choice if you’re ever in the hunter ring. Also, the leather is perforated, so maybe not the best choice for show boots.
Ariat Volant S - these are my general show boots when it’s mucky out or when I need to do a lot of walking. More solidly constructed foot than the V Sports and just slightly higher quality all over. Basically what you’d expect for $500 over the cheaper V Sports. They would be appropriate for any/all showing, and I’ve worn them in both the hunter and jumper ring.
Ariat Monaco Stretch - these are my show boots when I want to look nice (e.g. big class or when I wear my hunt coat). $700 (ish) My only complain about these boots is that the heights seem “off” in comparison to all of the other Ariat boots I’ve worn. And where I’m usually right in the “medium” height category, I sit right between the medium and talls in the Monaco stretch.
I still have my Sergios, Vogels, and a couple of lesser known brands, but mostly they just hold down the rug in my tack room!
I will add that I think what you’ve described with your boots is what eventually happens to most…especially if you fluctuate at all with your weight/size. I have a couple of pairs of boots (like my Vogels) that stretched over time to the point that I just don’t care to wear them any longer. Same thing happened with my old Ariat Volants (the red-stripe ones). I loved them for 2 or 3 years and then they stretched out in the leg to the point that they looked a bit like slouchy boots. My husband came out and took a bunch of pictures of me schooling my horses one day and I gave those boots away as soon as I saw the pictures…probably nothing that anyone else would care about, but boy had they become unflattering!
Anyhow, bottom line is that I don’t think you have to spend a bunch of money to get nice boots any longer. I think there are even several brands of “cheap” custom boots in addition to off-the-rack types. I seem to recall tidyrabbit mentioning custom tall boots that she has that were not terribly expensive and are super nice…maybe Eiki?