I think two things happen as you get older in this hobby, at least this is the case for me.
1. Your need for the newest and best gear diminishes as you become more practical and realize what you really need to enjoy hunting and increase your success. I remember when I was 18 years old and would drool over all the gadgets every time I received a new Cabela's catalog. Now I throw them away without looking because I know what I really need and can find it cheaper elsewhere. I would venture to guess that most of the folks selling an entire lot of Sitka clothing to upgrade to the newest camo pattern are the younger folks.
2. Growing to understand the value of quality gear. In middle age now (41) and thankfully having more disposable income than I had 20 years ago, I'm firmly in the camp of buy once, cry once. I buy good clothing, packs, boots, etc knowing it will make hunting more enjoyable if I'm warm and dry, and it will last a long time. I have a lot of old gear stuffed in the closet that never kept me comfortable but looked cool on the rack at Gander Mountain. A waste of money, and I won't do that again.
To each their own though. If you have a favorite wool jacket you hunt in, by all means keep wearing it. We should all live within our means and make practical decisions. Some upgrades are worth it and some not, and which ones you want are for you to decide. I still use my grandpa's old .308, buy the cheap game bags, drive a $15k truck and will never buy a new truck. Hell, I asked my mom to fix my grandpa's leather blaze orange hat for me last year because it will keep my head just as warm as the $70 Sitka ballistic beanie. I just hope there aren't too many gear heads out there that are having trouble making rent while they have a closet full of high end gear.