Jessica Biel

If Jessica Biel looks at this above photo of herself and goes to bury her head in shame, at least she knows that her husband, Justin Timberlake also has plenty of embarrassing photos out there of him – including one that makes our list. Which means it’s possible they would just share a laugh and move on with their night. But nobody would blame her if she still found herself embarrassed.

This outfit has several things that probably didn’t work nearly as well as she thought they did when she left the house.

The obvious suntan lines can be forgiven. The awful glasses, huge platform shoes, and ankle bracelet? Perhaps not so much. But hey, it was the ’90s!

Yet, she still managed to grab people’s attention with her amazing looks. Let’s not forget that prior to Justin, she was engaged to Chris Evans. So no matter how badly dressed she was, she had a lot going on for her.