I actually favor some items that get BETTER with age and use. Like the bearings on some bike gear that I have.
As for fly fishing stuff, I'm a lucky guy, can't think of anything that broke or was short-lived once the fly line manufacturers figured out floating lines should float... right out of the box!
Some favs for quality, as opposed to just expensive, in no particular order-
still going strong after 20+ years:
Matarelli Whip finisher- simple, elegant design, it still rocks the casbah. It amazes me that someone actually worked it all out. Reason enough for me to buy the original instead of less expensive knockoffs.
Patagonia SST jacket- great, you never seem to be too hot or too cold in it whatever the weather. It may be hard to justify at current prices, around 350 now, but was a great investment when i bought it at 160.
Billy Pate Bonefish and Tarpon reels. Heavy, built like a tank, indestructible. If you're in the market for a reel for tough fish but on a budget, it's not a bad option to look for a used one.
Regal Medallion (360 rotary) - Not the best vise for everyone or all tying, but it holds hooks rock solid, no adjustment for different sizes. With the old jaws i have i tie everything from 20 (with some effort and swearing) to 6/0. Somehow i ended up with 3 of them, with a backup for the back up...
Mustad hooks, the original ones, for most stuff these still work for me.
Luhr Jensen Hook Hone- one of those yellow handled jobs, about 7 bucks now. Great if you use large hooks, puts a cutting edge on 1,2,3.
Pfleuger Medalist- a good basic, simple reel, still fine for stuff that doesn't pull too hard. Still use old ones made in the USA as back up reels with odd lines.
Fenwick glass- my first big bucks rod at 35 bucks in the 60's, Still gets some use on small streams. They were the bomb back in the day, and it's still a sweet stick.
And after 10+ years
Hodgeman neoprene waders- don't know how they managed to last this long, but i still use the same pair for cold weather fishing. The only care they've received is to get hosed down once in awhile and thrown in the back of the truck out of sunlight.
Renzetti Tool Caddy- don't know why i like it so much, but it makes life easier at the bench, at about 20 bucks now it's still a bargain.
Tibor reels. Great for strong fish, when and if you need them. Overkill if you don't, but in this case you get what you pay for. The Charleton Mako is another reel in the same category now if you're in the market for a new one.
Sage sp's and rplx's still work great for me, sps for trout, rplx's for sw. These are the older 3 piece ones so are a pain to fly with now.
This has been a trip down memory lane- thanks for that.
Scientific Anglers System 5 reel, made by Hardy and also sold by them under their own brand as their Marquis model. Bought it in the early 1970s and it's still my reel of choice - 35 years and still going strong! Don't know what fly-fishing would be like without that "click-&-pawl" sound .
I'd also endorse Peregrines recommendation of his Sage SP, although I haven't had mine all that long (bought it "like new" on eBay after Sage discontinued them). However, mine is a 5-piece (plus the extra tip that Sage rods came with in those "good old days"), which makes it super-easy to travel with as its tube fits right into my carry-on luggage.
Folstaff wading staff. I've had it for almost 20 years, still going strong although it's pretty banged up. My second would be my Columbia fishing vest. It's badly smeared with floatant, seen a few dunkings and a lot of trecks through alders and shoulder high spruce. It's not pretty but holding up.
My RPLX 11 wt...Able 4N solid spool/back first model in camo...and a "relief pitcher" or back up reel a Teton Large Arbor 12...whilst its not the go to...it caught my largest fly rod Tarpon a while back...130-140 on my RPLX 11wt Two piece...'cause my beauty rods/reels were wrong, line, wrong leader, wrong fly...so the old stick and Teton did the job
Orvis '99' 2/1, 7.5', 5 weight bamboo rod finished on May 12, 1960 (I haven't owned it the whole time...it's older than me). The thing casts wonderfully, and with that impregnated finish, is bulletproof. I have fished it extremely hard for years and can't tell a difference in the condition from the day I bought it. I'm sure it will outlast me.