your mention of toolmakers & machinists keeping their tools in cigar boxes sure is a true description. I can remember many machinists and toolmakers digging thru cigar boxes of toolbits, reamers, and the like. If a job came along where they needed some form tool or perhaps a reamer ground a few tenths undersized, they went to their cigar boxes. Next to cigar boxes, the steel coffee cans of the 1950's (and earlier) were in widespread use. These were the shallow, larger diameter coffee cans that opened with a key. The lid of these steel coffee cans fit handily, so made a good container for small tooling. When I go thru lots of old tooling and come on the cigar boxes and coffee cans, it gives me a sense of who the machinist or toolmaker was.
In my own shop, I got a load of tooling with my 13" Roundhead Regal lathe. Some of the tooling was in a "Marsh-Wheeling" cigar box, and it advertised the cigars as a nickel (5 cents) apiece. The box was falling apart, but I saved the lid with the advertising. I can recall many of the old time machinists and toolmakers were cigar smokers, and often chomped the dead stub ends of the cigars thru the day. I got my Bridgeport, Powermatic band saw, another 10" Southbend lathe and a bunch more tooling as my share of buying up the estate of a deceased Swiss immigrant toolmaker. Plenty of cigar boxes & coffee cans full of tooling in the deceased toolmaker's shop. No wooden machinist chests (maybe the widow kept them).
Years ago, I sniped a Gerstner chest on ebay. It was a great price for a good chest, and other than needing new felt, was in fine shape. We gave it to a close friend as a gift. The exterior of the chest told a tale, with a few cigarette or cigar burns on the top lid. Either the previous owner of the chest was a careless smoker, or other people in the shop had a disregard for another person's property. The fellow who sold me the chest told me he got it at a shop liquidation down in New Jersey, so had no idea who the actual owner/user had been. I had visions of a toolmaker or machinist in a shop smelling of tapping fluid, soluble cutting oil, and cigar smoke, lit by hanging fluorescent lights, kind of a universal and unmistakeable atmosphere for anyone who has ever worked in an older machine shop.
Jim Rozen and some others here will recall the late Dave Sobel, the used machinery dealer and machine tool maven. Dave had his shop in an aggolmeration of garages out in Closter, New Jersey when I knew him. Dave was a cigar smoker and often had a half chomped portion of a dead stogie in his mouth. Similarly, ages ago, when I'd walk into the used machine tool dealers' stores on Centre Street or the surrounding 'used machinery district' in Manhattan, the smell was a mixture of machine oil, fresh enamel paint, and old cigar smoke. If I went to talk to the dealers, they often had a good chunk of a stogie in their jaws. So did many of the riggers and machinery movers who were out along the curb in those days, waiting for a sale to be made so they'd have a machinery moving job.
I was never a smoker, so never accumulated cigar boxes of my own. What I do have a LOT of is olive oil cans, originally 1 gallon Felipo Berio tins from some years back (when you could easily get a gallon of olive oil for a reasonable price), and plenty more of the newer 3 liter tins. These tins wind up as receptacles for bolts, nuts, drills, parts, small pipe fittings, etc and generally get set aside until I forget I ever had whatever was in those tins. In the past few years, I took to buying stackable plastic bins and sorting thru endless olive oil cans' contents, surprising myself with what was unearthed. I use the olive oil tins to load parts and tooling for particular jobs, handy if I need to set aside taper shank drills, reamers, and the like.
I agree about the 'name' on tooling or chests. Something like a firm joint or spring caliper or dividers is not going to matter whether it says "Starrett" or "Union" or made in some offshore place. Similarly, a chest that functions to hold tools is really all that matters. Whether it is a home-made chest with butt joints and plywood construction rather than quarter-sawn golden oak with dovetail joints, or a chest made by Union or Star or any other maker, if it holds a person's tools, it does the job. I used to think it was a certain class of people who attached significance to 'brand names' or 'labels' on clothing, automobiles, and much else, but thought of machinists and mechanics as less 'label conscious'. As I learned, that is often not the case, and machinist or mechanics can be just as fussy about the label or maker's name as any other group of people. My attitude is that if a tool is made right, feels right in use, and does the job, it is a good tool (or chest or much else).
Nowadays, the older cigar boxes and shallow/large diameter coffee tins are 'collectable' and are sold at flea markets and antique stores. Cigar smoking or any smoking in the workplace (or many other places) is forbidden, and people are more health conscious. The days of machinists or toolmakers working with a half chomped stogie in their craws is probably long past.