Well, I rode English yesterday and so donned some boots and breeches just for grins. Did not wear my old white pegged cotton breeches- which were not new when a friend gave them to me in 1985 or so- because they are buried a bit deep in that closet and I just grabbed the first pair I came to. But I did wear the brown field boots given to me by another friend about the same time- he'd found them in his late grandmother's attic when his family cleaned out her house. The lining says 'made in England for Abercrombie and Fitch,' and best he could figure, she probably obtained them around the 1920-21 time frame. So, I think it's safe to say they are 85 or so years old. Last time I had them re-heeled (and had some rotted stitching repaired)- the boot surgeon said don't bring them back, the leather won't hold the stitching any more- but so far so good!
My fringed and buckstitched western chaps, which I still wear frequently, I bought in 1969. Recently gave the 1967 vintage chaps to the barn owner, and have seen her daughter wearing them.
I have a pair of Jodphurs my mother got at Lilly Whites in London before I was born. I would use them if I could fit her 23 inch waist! They are beautiful. I can wear her canary breeches from Saks with button up legs but love them so much I hate to put any more wear and tear on them.
I have some old TS's (knee patched replaced once per pair) that are at least 16 years old. My full chaps are aboit 18 years old. The end of the zippers have broken off when after the freshman 15 (lbs) I needed to use a hoof pick through the hole to zip them close. Fortunately, I now fit back into them.
I still have a pair of rust breeches that I used to show in, oh gosh, the late 70's, early 80's... I can still get them on, but they are a tad tight-and made of all polyester, no less... I rode in them last year just for laughs, but man, they made me hot compared to the nice cotton blend breeches we can get now!
I gave a pair of calf-top riding boots to a good friend of mine that I had custom made at Swaine Adeney Briggs in Piccadily London in 1973 (won em' in a horse show...they've got good prizes over there). Sadly, my calves got too large to ride in them...great boots.
Today I rode in a pair of Elk chaps from 1983 I had made by "Jeff Straws Tack & Togs" in Lovettsville, VA...I don't think they're in business any more.
I have a pair of Eurostar breeches that are about 20 years old and are still going strong. I also still occasionally ride in a pair of Vogels that were made in 1987. They have been resoled a couple of times and the leather is starting to crack but they still fit and are fine for schooling.
I have a hacking jacket - bullet-proof tweed - that my father used to cub in. I've worn it to hounds a few times. The tailor's tag inside says it was completed December of 1935.
I also regularly use a stock that was his that is at least 40 years old.