What is your oldest possession that you bought with money that you earned that you still have in your possession. Not something that was passed down or given to you. Not something you bought with money that was given to you either.
Mine is a LYNYRD SKYNYRD album I bought in 1976 when I was 17 (Pronounced 'Lĕh-'nérd 'Skin-'nérd). 2nd oldest is my Remington 700 ADL - .270 caliber (August of 1977) that I still use today.

My wife’s uptops. They’re turning into lowtops though.

Pics or it did not happen.

Those 38 DD's turning into 42 longs?

A used Winchester Model 25 12 gauge I bought from the Nacogdoches Army Surplus store in about 1964. They let me pay it out weekly, but also let me take it home the first day. Still have it in the safe.

I bought the same album
It is great

Nothing wrong with that, It gets all the toys gathered closer together.

Without all the qualifiers, my oldest possessions that I still have and use, are a Craftsman socket set and wrenches that I got for Christmas 1965 or so. A few sockets are missing of course, but the rest still good.

Cookbook from the late 1800's. I'm at work, so I can't put my hands on it, but it's an old church or community cookbook and I think it's 1878, but not positive. I've had it for over 20 years. I love old cookbooks. I'll try to remember to look when I get home and post it.

Kinda what I was thinking too. Skeeter. I have baseball mit I earned money for at age 6

My Ithaca model 37 featherlight 20 gauge that i bought on my 16th birthday.

Some collectible postage stamps I bought as a kid over 55 years ago, tossed in a metal box and forgot about.

Early 1900s roll top desk.

Great question given the parameters. I can’t think of anything I still have that I bought years ago. Maybe my ping eye3 blades from around 99-2000. I have a few shotguns from early 2000s and a Taurus revolver bought around 1990. I don’t like to keep things that aren’t really worth much (except the Taurus )

1958 Remington 870 wingmaster pump 3 inch magnum/30 inch full choke barel...bought in 1963 used from Oshmans in Houston to hunt geese on prairie outside katy,Texas.....