Horses can be a black hole as far as money is concerned. With the way the expenses can add up, it can be easy to want to take a frugal approach to gear. But there are a few things we feel are worth their weight in gold as far as horse longevity and handling go. Natural materials (leather, wood, rawhide, wool) can be kept clean and cared for so they will last for years and years. Well-made tack and gear are a big cost up front, but in the long run can work out to less cost over the course of a lifetime because they don't break down or lead to vet bills.
Here's a short list of good gear we wish we'd invested in sooner.
a good rope
Not a roping rope: just the rope you lead your horse around with. Just the rope that connects you to your horse before and after the ride, the rope that you do groundwork with, that translates your signals to the halter on your horse's face. That rope. You can choose between spending $2.99 on a lifeless cotton or poly lead, or you can spend $20 on a rope that will give you a whole different level of communication.
good boots and stirrups
If you want to do one thing to dramatically increase your chances of coming through a wreck without serious injury, this is it. A leather-soled boot resting in a deep leather-lined or wood-lined stirrup will not only increase your ability to use your foot and lower-leg properly, it will allow your foot to slip free in case of an accident. Rubber on rubber has no feel and a lot of friction. Rubber on leather has slightly better feel and slightly less friction. Leather on leather is the kind of thing that once you feel, you'll never go back.
a good pad
Of course in an ideal world we'd all be riding in hand-made saddles with custom wood trees, but as dropping a few thousand dollars on a saddle is sadly beyond what is possible for some people, a good pad can go a long way in terms of offsetting any inconsistencies of fit problems in your saddle. While synthetic pads can break down in unpredictable ways, a good solid wool pad will last a long time. These five star pads, in particular, can last a decade.