@fbaezer,
Following fbaezer's idea -
1)
1961
When I was first in college, very early sixties, the continental suit was all the rage. My Music 1A - TA wore one. He was very cool and had wonderful eyes. Oh, and yes, this great suit. He had a certain presence.
I've looked online before and never found any suits that look like those that were popular for those months or years, so, I've no photo. Just picture good eyes on a smart man and pretend that's me.
My continental suit would probably be grey or khaki color, though many were a kind of green, and I'd have a pale button down shirt (not white) and penny loafers, even though those always hurt my feet. I don't remember about tie, I think not. Probably open top button. Great haircut.
Good music in background.
2)
1980's
I was studying and then working in landscape architecture then, and this involved going out and tromping around sites, sometimes muddy sites. I've only known one female who did that in high heels, and she was good enough to get away with it. Anyway, most of us females wore jeans, a good shirt, blazer or some sturdy less formal jacket and clogs or boots... unless it was some city meeting, and then I'd wear my good white suit or something equivalent. Or not, depending on the city.
So, were I a man - same thing, but not clogs, unless I could find Man danskos and they didn't look odd.
In summer, jeans or slacks, depending on job, long sleeved shirt rolled up, probably brown leather shoes with both style and comfort, worn with air of authority willing to listen. Probably carrying olden weathered satchel, maybe even my own. (my own whatchallit briefcase is has gone from navy to blue grey)
3.
2010.
I'm still interested in clothes but way less interested in norms. My clothes source is Good Will. I'm retired and not rolling in coins, but I bought from thrifts even back in the work decades.
By now, I might even wear cowboy boots, but that looks plain silly in some places, so it would depend on where I live. Work boots, or shoes that don't f-kn hurt my feet, comfortable loafers.
I'd still like rolled up long sleeve shirts - maybe like the one osso fell in love with a guy over, a rich marine blue, oh, and his eyes, and the stuff behind the eyes (he's a real person, wish I could show the photo) - but now that I'm older I might have some good slacks instead of jeans. No ties. I don't go to those kind of restaurants, or to the opera. I'd still try to have a good haircut (even though osso has given up on that herself and cuts her own) including if I were bald, which, is, of course, beautiful.