Articles of wearing apparel always associated with one creative work/person

Actual weapons on her brassiere = Lady Gaga

Blue and white striped scarf + red and blue striped sweater = Mark Cohen, RENT
Huge, multicolor/patterned sweater = Bill Cosby
Red and black striped shirt + black shorts = Calvin
Red and white striped shirt + matching toque = Waldo

And, of course, these.

You forgot Boss Hogg.

Freaky/flappy/asymetrical jackets/tunics - Dorothy Sbornak (Bea Arthur).

Lady Gaga’s got her beat

Sloppy bathrobe and muscle pants - The Dude

Tall headdress made of tropical fruit - Carmen Miranda

White fright wig - Andy Warhol.

Beautiful evening gowns - Nancy Wilson (jazz singer).

Crazy-pattern sweaters - Bill Cosby.

Gentleman’s hat with price tag still on it: the Mad Hatter.

The hat and cigarette holder for Hunter S. Thompson.

Rerun was in What’s Happening!!

Oversized brown fedora - a certain archeologist whose name escapes me.

Large necklaced timepiece - Flava Flav

Alpine hat and short velour jacket - Chico Marx
Beat up top hat and rumpled trench coat - Harpo Marx

Sloppy white bathrobe, guinea t-shirt, and boxer shorts - Tony Soprano

A toga of green leaves-Jolly Green Giant

A 20 foot scarf and Hat-Dr Who (Tom Baker)

Deerstalker cap - Sherlock Holmes (doesn’t really matter that it was Sidney Paget who added it, the association is there).

Black coat, white shoes, black hat - Jim Parker

Crooked, tall, horizontally-striped hat - Cat in the Hat.

Roller skates - Rollergirl (Heather Graham)

Ascot - Fred on Scooby Doo

Well not apparel but part of the dress, that one of a kind long slender pointed tip microphone-Gene Rayburn

Loincloth - Tarzan

Which he apparently designed or invented.

Studded, white jumpsuit - Elvis

Bad mother-[shet-yo-mouf]-ing leather jacket - Shaft, John Shaft.

Leather jacket - The Fonz.