Do it! Theres a good few on eBay already so the market is there. I love and collect old-school tech company work shirts. Once literally bought the shirt off a guys back out one night because he had a nice DELL shirt. Offered him €10 for it and he took it and was immediately escorted off the premises for being topless.

Have about 6 so far and my most prized one is the red IBM shirt. IBM! RED! It's brilliant. Now, While I love them, the cut on these shirts is absolute crap. Fits grand on neck and wrist but is the poofiest thing everywhere else. You yanks! Would pay extra to have it cut to a better fit.

In terms of market, if you get the brand right you might be able to skirt both earnest tech-heads and the Vaporwave kids who like this kind of stuff: http://www.ebay.ie/itm/Japanese-Windows-Long-Sleeve-Tee-T-Sh...

I have a Windows ME pen lying around here somewhere.