Since we're at the end of the year now, I think it's time to award the "Cheesiest Dresser of the Year Award". I am going to have to say, without bias, Heidi Montag. (I say without bias because I don't watch her show; and I've heard that if you do, one would have even more reason to dislike her.)
Here are some classic examples:
Yikes, I hope she had this dress taped on because her ridiculous fake boobs are about to fall out. And check out the hooker shoes, um, yuck!

This I don't even need to comment on, it speaks for itself.

Here we've got some really dumb looking and too short high waisted shorts with a weird scarf-shirt thing. Chanel sandals and an Hermes bag cannot even come close to redeeming this.

This dress looks like polyester that cost $10, it's what a hooker wears when she's trying to dress up and look proper. And the shoes... uggghhhh!

Again horrible shoes, and why is she carrying that bag? Totally doesn't match. The dress could have worked if she could ever mange to keep things simple.

Hot? No, just nasty and cheap looking. And sorry, those thighs are just not thin enough to wear shorts that short.

It's clearly a very sad case. I wish her better luck in 2009.