Julie Bowen

Steve Granitz/WireImage

There's a fine line between casual and underdressed, and as far as we're concerned, these five stars have crossed it. No, it's not easy to throw on a skintight cocktail dress or ball gown every time you have to strut it in front of the paparazzi, but the valley between high fashion and way-too-lowbrow is wide. Sadly, these celebs ended up on the wrong side of the divide.

First up is America's favorite TV mom, Julie Bowen, in a lovely look for a Saturday brunch with the girls. We can get behind the black pencil skirt and modern sandal, but the white T-shirt and denim jacket are too blah for this moment.

Chelsea Handler

JB Lacroix/WireImage

Chelsea Handler gets more dressed up for a taping of her show than she did for this paparazzi-snapped event, and to make matters worse, she was photographed next to the ever-glamorous Gwyneth Paltrow, who wore a leather LBD. It's not that the talk show topper looks bad. In fact, those pants are a perfect fit. But this whole getup says "Friday night at the movies."

Shailene Woodley

Sean O'Neill, PacificCoastNews.com

Harsh as this may sound, if we were a hot, young starlet like Shailene Woodley premiering the season's most anticipated film, we'd try a little harder. Apparently the Divergent actress isn't a fan of fussy fashion, but that doesn't excuse a bulky sweater for a major movie-promoting moment.

Zosia Mamet

Craig Barritt/Getty Images

Finally, it's Zosia Mamet in what looks like her PJ's with a jacket on top. We should provide the disclaimer that this shot is from an off-Broadway play in NYC and not a red carpet in LA, but we've seen the Girls' star give her fashion much more thought for a much lesser event.

We'll forgo the "who wore it worst" for this set of fashion misses, but the mention should be inspiration enough to up the ante next time around.

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