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Evening Pony: Jessica Simpson
While Simpson's style is unique and fun, it's a little too styled for what should be a casual evening look. For a concept that is intended to say, "devil-may-care" it screams, "this took a lot of work!" Evening Pony Winner: Underwood.

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Big Blowout: Jessica Simpson
Who wouldn't want to walk out their front door looking like this? With this long hairstyle, Simpson embodies the iconic California girl here with her smoky eyes and understated lips.

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Big Blowout: Carrie Underwood
Ms. Underwood looks fresh and sexy with long locks blown out big. Any of us would likely be delighted to go out the door with this look, as much as Simpson's. But Simpson's style looks more carefree and unfussy. Big Blowout Winner: Simpson.

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Tight Waves: Carrie Underwood
During her "American Idol" run, Underwood wore this fun full head of pronounced waves. It's a great onstage look and flatters her face.

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Tight Waves: Jessica Simpson
Simpson sported her tight waves during her heyday, while still married to Nick Lachey. These waves look so good, they could pass for natural curl. It's a close call, but Simpson's more natural look is superior. Tight Waves Winner: Simpson.

The similarities between these two fair-haired songbirds is striking (beyond boy-toy choices). Whether you're on Team Jess or Team Carrie (or you're cheering for both), it's clear they're both style icons in their own right. But which diva takes the crown in a direct faceoff? Let's find out ...
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