I think this is something I will start doing on a semi-regular basis. How to wear vintage - or, how not to wear it! Not that you people are dummies; but sometimes a little illumination on a matter puts something simple or basic into a whole new light. (Gee how obvious! Illumination usually does put things into light.... :))
Nevertheless: the possibilities with a vintage piece are endless; as with any good wardrobe pieces; vintage or otherwise. I don't usually dress in head to toe vintage. That is just not always practical. I usually focus on one vintage piece - a skirt, a velvet jacket, a hat, a dress, shoes.
For example: Behold, the plain, old, pleated, plaid, 1970's-ish skirt. Blah on the hanger. Hideous to some, perhaps. My mother used to put these on me all the time; with tights, buckle shoes, sweaters or blouses. She worked that schoolgirl look with these skirts.
I found one the other day on a clearance rack at the Goodwill. I will not tell you how much - or little - I paid. It might make you sick.
Tights, Mary Jane's, a black sweater, and a velvet beret, and I am transformed from a humble looking American girl into a Bonny Highland Lass!
If only I had a pair of knee high wellington boots, I might keep this skirt, and wear it to muck out stalls properly, like a lady.
You might hate plaids, or pleated out of date skirts, (I myself was sceptical about even buying it in the first place) but this look is timeless.