This craftsman is early to mid 60's I think.
We inherited these both from a family friend years ago. The cornwell is kind of a pain, but the Craftsman is a quality unit.
You can find the production date in the vicinity of the left corner of the top till on the upper, and near the right-hand side of the bottom rail on the lower.
That Craftsman unit is in beautiful condition for being around 50 years old!
So, here I was, happy to have found this thread on vintage tool boxes, because that other "show your tool box" thread with all those giant modern boxes is sort of intimidating, and then m0ondoggy posts his incredibly clean 50 year old Craftsman, and now I'm intimidated all over again,

but here goes anyway...
These are a few of my vintage ones, starting with some Craftsmans. I've never had one of those giant modern boxes. We weren’t allocated enough shop space for much more than a single-stack. When I used to be a field tech, we carried our tools in a really big shiny box, but it had dual rear wheels and a V8 or diesel engine.
Craftsman machinist's chest, c1950s. Original finish. I had to replace the felt in 2 of the drawers, and do a lot of cleaning and polishing on the wood, but otherwise the box was in pretty good shape when I got it about 10 years ago:
Craftsman 65262 6-drawer chest (1/73) and 65035 5-drawer roller cabinet (10/72). Original finish, one owner. These were home boxes, not for work, so they've stayed pretty clean. The roller cabinet was a Christmas present in '72 and I bought the chest a couple of months later. Didn't have enough money to buy the 10-drawer chest like m0ondoggy's,

had to settle for the 6-drawer. Hey, we had a new baby and a lot of bills, and skipping those four extra drawers bought a lot of strained carrots.

Original paperwork in the rack on the lid:
Next is a Craftsman 65039 roller cabinet from 1975. I bought it around Y2K. It's a little beat up, but not too bad. Some of the drawers needed a little tin-knocking and slide repairs. I took the wheels off to line it up as an extension for a workbench:
Moving on from Craftsman, a Snap-On Rolla-Bench, including the optional KR-431 3-drawer lower section, topped off with a 1980 Proto 9939 3-drawer chest made by Waterloo. I think the Rolla-Bench is a late 1940s KR-300:
