But she revealed a bit too much cleavage when she attended Art Basel Miami Beach 2012 on Wednesday.
The talk show host and funnywoman sported a toga style strapless two-tone dress in black and cream colours.
Revealing: Chelsea Handler put lots of cleavage on display in a toga style dress at Art Basel Miami Beach 2012 on Wednesday
Chelsea also sported a pair of androgynous black brogues and minimal make-up, and looked fresh from the beach as she scraped her blonde tresses into a bun.
The day before the comedienne had attended the kick-off party for the annual event.
No one is looking at the art: The comedienne provided quite he distraction in her low-cut two-tone frock
Good at making friends: Chelsea merrily threw her arms around another guest at the bash
Star-studded: Diddy was also in attendance and posed up at the preview with socialite Isabelle Bscher
Will Ferrell was dressed very casually to peruse the artwork on offer alongside his wife Viveca Paulin, paying particular interest to the modern paintings on offer.
The actor was sporting an Irish football shirt, beige chinos and a very bushy moustache, also going incognito in a baseball cap and sunglasses.
Owen Wilson was also hoping to go unnoticed in his baseball cap, which he paired with a T-shirt and simple trousers.
Art attack: Will Ferrell and his wife Viveca Paulin seemed smitten with some of the modern paintings
Fancy seeing you here: Chelsea and her pal chatted away to Will and his other half
Low-key: Like Will, Owen Wilson attempted to go incognito with a baseball hat and sunglasses at the ready
Bringing the glamour: Ana Beatriz Barros (L) and Diane von Furstenberg provided even more colour with their bright trousers
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