Gobs of heavy gold jewelry and a mohawk: Mr. T
Gobs of make-up, shiny dresses with shoulder pads, and expensive jewelry: Joan Collins
Too small grey suit, red bowtie, white patent leather shoes: PeeWee Herman
White or gray v-necked shirt with the sleeves rolled up - Simon Cowell.
Flip-up shades - Dwayne “Chipmunk” Wayne.
Maybe a bit of a fetch but certainly if you came of age in the 80s:
Aviator Sunglasses from Tom Cruise in Top Gun
And the ghost costume on E.T. (I know that Charlie Brown tried to capitalize on the look in his Halloween special)
Head full of fruit: Carmen Miranda
“Ugly Ass Shoes” bloodied Bruno Magli Shoes - O J Simpson
The word “DICK” scrawled in Sharpie across the forehead: My old college roommate (the boy couldn’t hold his liquor).
Oxblood red leather - Kevin Sorbo, Andromeda. Something tight, black, ripped, mesh, or kinky - Becca, Andromeda. Also, Tyr.
White buckskin shoes: Pat Boone
Huge bandanna in hair: Bret Michaels.
Triangular green collar–Kermit the Frog
Hat & necktie–Fozzie Bear
Ragged grey toga and walking stick–Yoda
White suits used to have a more general symbolism: feudal overlords from warm climates. Think South America, or The South of America. Think political bosses, planters, “big daddies,” and showy wastrel layabouts with shiny hair.
Twain and Wolfe surely got away with their attire because they were plausible as part of the stereotype. Col. Sanders too.
Cape - James Brown
Browline glasses - Malcolm X
*Brown Eyed Girl, I see I edited after you posted about Mr. T. I think you may have beat me to him. I pity the fool that beats me to him.
Closely-cut blue suit and blue bow tie: Uncle Ben
Loud cocktail dress with fringe, feather boa, cigarette holder: Phyllis Diller
I’ll stick with my choice, thank you very much 
Form-fitting leather jumpsuit - Emma Peel (“the Avengers”)
Bowler hat, umbrella - John Steed (“the Avengers”)
the Puffy shirt
the Urban Sombrero
the pocket-less trench coat
- “Seinfeld”
A number of them:
The gray, collarless, 3-button suit, with pointed black boots, thin black tie.
The tan, Nehru jacket uniforms from Shea.
Brightly colored, whimsical variations on old-time band member costumes.
Each of these, staples of tribute bands the world over for how easily they evoke the image of…the Beatles.
We’ve gotten this far and no one’s mentioned Steve Urkel and his saddle oxfords (plus high-water pants and nerd glasses)?
Fig leaves Adam and Eve
Black turtleneck and blue jeans: Steve Jobs