My vote would go to Rodney Dangerfield. Or the pope.
Any dude.
Barbra Streisand, Tonya Harding & Grace Jones.
channels jarbaby
Oh, and Bea Arthur.
Came in to post Bea Arthur, but since she has been taken, I will go with Louie Anderson.
Phyllis Diller.
Michael Moore, please come pick up your thread.
Taking the thread title as literally as possible, the celebrity I would like to see wearing the MOST clothing would be:
Danny Devito. It would be really cute to see him wearing like 5 shirts and 5 jackets and a snow parka and a couple of mufflers, and a hooded sweatshirt and couple of baseball caps and like 9 pairs of pants. Wouldn’t it? He would just look like a big ball of yarn. Wouldn’t he?
What just crossed in my head was the episode of Friends where Joey puts on all of Chandler’s clothes, and the episode where Danny Devito plays the stripper.
Uuummmm…
James Garner.
Marlon Brando
Roseanne
Jerry Springer
Can I change my answer or just add to it Dr. Phil?
He’s worth mentioning. 
Last night I watched a few minutes of the Selena movie and had the great misfortune to see Edward James Olmos in his underwear. That’s bad enough, I can’t think of anything worse.
I, too, would like to add to my nominations. Kathy Bates in “Primary Colors” caused me to curl up in fetal position and weep.
Jessica Simpson.
Because I would probably get aroused at the sight, and the last thing I want is to be aroused by that idiot bimbo.
What’s wrong with Grace Jones? Has she not aged well?
Oh, and DO NOT use Google images to remind yourself of what Tonya Harding looks like.
Really. Don’t.
Carol Channing was on the Tonys and was unsettling just by exposing her calves.
So her.
If she was still alive, Anne Ramsey. Link
Darned, those Bea Arthur votes came in fast and furious.
Okay then, my second choice would be Abe Vigoda.
That would be cute. At first, I just skimmed your post, saw Danny Devito, assumed we were still talking naked, and thought to myself, “disgusting.”
I vote for Marlon Brando. That would ruin The Godfather for me.
Marlon Brando…
Rush Limbaugh.
Oh, and once I told my sister I’d seen a picture of Pat Buchanan in his underwear. She told me she’d have nightmares for a week just from the thought.