Started thinking about this topic after splashing out recently for numbers 1 and 2. I am by nature as cheap as the day is long, but experience has taught me that going with the cheapest equestrian or equine product can be pretty costly in the long run. I can't tell you how many times I have gone the cheap route and ended up buying 2-3 times instead of once with 1 high quality product. I will say though, that customer reviews on so many different websites do make choosing a price point a lot easier. I am much more comfortable going high or low if the reviews are there and enough buyers have strong opinions.
1. Stickyseat WindPro full seat breeches. The bomb. Well constructed, super grip, very warm, and long enough. Not particularly cheap but really comfortable.
2. Mountain Horse Stella Polaris Winter Boot. Great fit, super comfy, waterproof, warm, look pretty good for winter riding boots. I struggled with spending the extra $90 compared to my next choice but I really, really like riding in these boots. They are actually comfy to use for barn chores as well.
3. Horseware Rhino Wug. Mid-price point for a heavy turnout but decent quality. Holds up over multiple years and looks pretty sharp. Very warm.
4. Red Snap'r T-Post Cap Insulator. We would all love to live in a world of endless 4 board fences and no t-posts, but when compromises have to be made with fencing, these make t-post so much safer. Cheap too.
5. Smartpak Small Diamond Deluxe Dressage Saddle Pad with Monogram. Decent price point, very nice quality, hold up well. First one of theses I ordered had stitches that were not complete leading to a hole in the trim a few weeks later. Smartpak replaced no questions asked including monogram. A big fan of Smartpak in general.
There you have it. Nothing earthshaking, but a few things I have felt like were totally worth the money.