One spangled white glove–Michael Jakcson
Too tight black gloves–O J Simpson
Glass slippers–Cinderella
Ruby red slippers–Dorothy in Wizard of Oz
Red shirt–Star Trek
Black Wayfarers - Joel Goodson in Risky Business
Batman’s cowl
The guy that played Rerun in"Good Times" - Red beret and suspenders
Mark Twain’s white suit and hat.
FDR’s cigarette holder.
Glasses (with mustache) and cigar – Groucho Marx
glass slipper – Cinderella
At least until Tom Wolfe showed up
Mentioned in OP
Plaid shirt: Al Borland
bowler hat and cane - Charlie Chaplin
pipe and cape and deerstalker hat- Sherlock Holmes
Shirt with black horizontal zig-zag stripe - Charlie Brown
Absurdly long scarf - Doctor Who (specifically, the fourth Doctor, Tom Baker)
Monocle - Sir Patrick Moore.
1st runner up - Isadora Duncan.
Spike heels, black fishnets and a garter belt = **Bettie Page **FTW!
Or Colonel Klink.
Or Mr. Peanut.
Ladies’ hat with price tag still on it: Minnie Pearl
Necktie curled up at the bottom – Dilbert.
Round wire-framed eyeglasses - John Lennon
Purple suit – The Joker.
Crooked stripe shirt-Charlie Brown
Not apparel- Linus’ blanket
Blue Sailor Outfit - Donald Duck
Red…um…shorts? And apparently giant yellow Crocs - Mickey Mouse