There are certain milestones that quietly remind you how long you’ve been doing something. For me, that milestone came in the form of a new pair of tall riding boots.
After recently upgrading my riding helmet, I decided it was time to take a look at the rest of my riding attire. For the past several years, I’ve been riding in paddock boots and half chaps, and both were showing their age. Since I needed to replace both anyway, I started considering another option: going back to tall boots.
It had been more than two decades since I last purchased a new pair.
While I’ve continued riding on and off over the years, it had been a very long time since I experienced the excitement—and slight apprehension—of breaking in a brand-new pair of tall boots.
If you’ve been around horses long enough, you probably remember the days before zippers became standard. Breaking in a new pair of boots was practically a rite of passage. There were boot pulls to help get them on, boot jacks to help pry them off, and plenty of sore knees and ankles in between. The leather was stiff, unforgiving, and seemed determined to test your commitment to the sport.
Thankfully, tall boots have come a long way.
The pair I chose features a back zipper, making them far easier to put on and take off than the boots I wore as a teenager. The leather is also noticeably softer and more flexible right out of the box. While they still require some breaking in, the process feels much less intimidating than I remember.
The transition from paddock boots and half chaps to tall boots has also been a nice change. There’s something about zipping up a pair of tall boots that makes you feel a little more polished and put together in the saddle. It brings back memories of my early riding days while also feeling like a step forward as I continue building this chapter of my equestrian journey.
As I’ve returned to riding more consistently, I’ve found myself making more intentional investments in my equipment. Safety was the driving force behind replacing my helmet, and comfort, fit, and longevity played a big role in choosing new boots.
The sport has evolved, and so has the equipment. And while my new boots and I still have a few rides ahead before they’re fully broken in, I’m grateful that the days of wrestling with boot pulls and boot jacks are mostly behind us.
For anyone who remembers those days, that’s a pretty welcome upgrade.
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