I guess you can't fairly judge the fashion sense of someone who climbed the Hollywood ladder by taking her clothes off for Playboy and E! cameras. But, let's just say that former Hugh Hefner girlfriend Holly Madison should have never taken a page out of her buddy Kendra Wilkinson's tomboy book.

Cue the childish entrance of Holly Madison wearing a loose Iron Maiden t-shirt, covering up her "charms" and leaving a lot to the imagination. Scroll down to find a short, cheap, denim miniskirt and yellow striped tube socks. What can you use to complete the outfit? Oh, of course! High Top Mod Print Chuck Taylor's. Maybe she is better off wearing nothing at all.

See more photos of Holly Madison.

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