Equestrian confession: I have never owned a pair of tall boots. I’ve never needed them. Up until the last three months, I never thought I would┬áneed them because I didn’t want to show.

However, I do need new boots in some fashion. My paddock boots are old and beat up, and the suede half chaps I bought last year are getting there as well. When I told my trainer that I was in the market for new boots, she suggested I get tall boots because they’d last longer than my half chaps and I could show in them, since I’ve now decided that’s a thing I want to try. So on Saturday, I went boot shopping.

On the recommendation of my trainer and also general good sense because their return policy is awesome, I went to Dover. I explained to the lovely and helpful salesgirl that I had ridiculously muscular calves and thought I might be a tough fit, that I knew nothing about tall boots, and that I’d like something in the $200-$250 range that was appropriate for schooling-to-show. The girl gave my legs the once-over and said, “You should be fine to fit. We’ll try a regular medium calf.”

You should know where this is going by now.

Several pairs of boots (and several skin-pinches) later, we had only found one pair of boots that even remotely fit my leg properly. It’s what the girl called a “sock style” boot, meaning that the leather was incredibly soft and hugs the leg like a second skin. They were actually super comfortable, except for the fact that they were a dress boot (rather than a field boot) and I couldn’t really bend my ankle. The salesgirl swore the boots would stretch and allow my ankle to bend, but she also told me that the stock-style boots don’t have a break-in period, and those two things seemed contradictory. The other issue is that the leather of the boot was so soft that I really think that the fit of the boot wouldn’t be maintained past a few months; once it broke in properly, the boots would probably drop and bag, just like my regular “going-out” boots that I wear to work.

You can just tell these will sag after a few good rides. Also you can see all the “fallen soldier” boots behind me that just didn’t fit.
Bagging was the issue in general: because my ankles are so slender (8 inches in diameter) compared to my calves (15.75 inches standing, 16.25 sitting), what fits me in one place logically doesn’t fit me in the other. The girl at Dover told me I’d probably need a custom boot, which, with wedding payments and general living, isn’t a possibility right now, especially when I don’t even know if I’ll like showing. We tried a leather half-chap with a zip-up paddock boot, but I had the problem again with the bagging in the ankle.

My trainer seems less concerned about my boot-shopping woes than I am. She says to go boot shopping with her next time, and we’ll find something – boot or half-chap – that works. Right now, we’re both on the same page: lace-up paddock boots (because I’ll get a better fit and more mobility through my ankle) and a decent leather half-chap are probably the way to go.

The hunt continues.