Best clothes I had in the '80s? Easy.
Surplus, brand-new West German army tank driver's overalls, with the little flags on the shoulders. Looked really cool and it saved having to wash lots of extra shirts and jeans in time for morning classes. Just zip my way into the "Kombi-Anzug" and away I went! I even remember playing in rock and R 'n' B bands on stage wearing it.
"Bundeswear" is ubiquitous nowadays, but back then, ca. 1986, it was hard to find in good shape- this one was so new, and in such good shape, it even has the built-in holster inside, and lotsa pockets, everywhere. I still find money in the odd pocket or two when I move it around in the closet. :^)
Of course, the left wing professors I had to deal with looked askance at it, but, fack 'em.
Now that I've dumped about fifty pounds, maybe I might be able to fit back into it again....