Oooh, I'd forgotten about Schiaparelli, Funnys! Now she was witty, through and through. Cheers for the reminder :)
Plush doggy jacket witty if worn 'ironically', which would probably make the wearer a bit of a prat.
Puffy dangly muppet togs more slapstick than wit. Good fun, though.
Yoko's new line for men sounds quite 'witty', Harpy ... I think I'd prefer less sexual overtness all round but, if we must have it, let's get the chaps back in tights & codpieces 
Audrey Hepburn was a 'witty' dresser. She'd often have some outsized accessory or something worn at an unusual angle - made you look twice. Katharine was equally stylish, but serious.
Why the fuck am I going on about fashion? I need to get dressed!