The oldest piece of gear i use on a regular basis is a Wittnauer watch-case compass from the 40s. I just like it.
I have a brass cigarette lighter from sometime back around then as well.
I have several un-dated pieces of steel that i like as well, to include a Western L-66 knife and a Norlund axe.
I have a 70s-era NATO/Bundeswehr canvas pack that is my dayhike/hunting pack, and a German mess kit that i like for day hikes.
I have a Coleman 2-burner camp stove and 2 lanterns that probably date into the 70s or 80s.
My recurve bow is a Bear Grizzley from the mid-70s.
All of these are things i've acquired in the last 5-10 years or so.
The oldest piece of gear I still have from childhood/scouting is a Silva compass. I had my old mess kit, yucca pack, and a screwtop match safe, but i sold them at a garage sale in 2007. Never used them, but i probably gave them away too cheaply. I still have my childhood Zebco 202 rod and reel, but don't use them. I do have fishing lures though, from back then, that i still use.
I have several of my childhood pocket knives, but they don't go out of the house anymore... i'd be crushed if i lost one of them, especially the Camillus Barlow.
I also have a thermarest mat and a Coleman model single burner stove from 1992 (my daughter still uses the mat.)
I had a pair of wool longjohns (they were my dads before i 'stole' them when i left home in 1982. he was issued them in the navy in 1958). I retired them this year, finally worn out after 54 years of service). Now that i think about that, i also have a couple army surplus wool goods (field pants and field shirt) that could be as old.