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The Short Sleeve Sleeve Sweater & Long Sleeve Shirt Combo

Points For: Versatility

Why: The shirt underneath would still hold up in Cool Outfit Court without the boxy sweater, too. It's all about the way the long hem and oversize dimensions play against those skinny jeans.

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The Short Sleeve Coat Layer

Points For: Freshness

Why: Since they're less common, there's something about the short sleeve coat layer that's just so strikingly crisp. And you won't fully realize it until you just take the leap and buy one, but you know what? There are actually a lot of days that are perfect for short sleeve coat wearing.

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The Belted Denim Jacket

Points For: Versatility

Why: Cinching a denim jacket with a thin belt gives it a tailored feel we love. But the white maxi dress underneath would be pretty great without it, too, since she's still got that wide brim hat on top to add a dose of glamour.

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The Shorts and Tights Combo

Points For: Freshness

Why: Stretch your shorts-wearing into chilly days by pulling a pair of super-thick, opaque tights on underneath them. It's a look Olivia Palermo loves (and she looks awesome almost always), and it's also surprisingly warm.

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The Statement Vest

Points For: Freshness

Why: The statement vest doesn't come out as much as the statement jacket, so when it does it makes a big, big impact.

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The Hooded Scarf/Snood and Bare Legs Combo

Points For: Versatility

Why: I make up a different statistic every time, but I think it's like 80 percent of your body heat gets that lost through your head, and that's why hats are crucial–or, in this case, hooded scarves. Start your morning with one like this, then toss it in your bag as the day gets warmer and you get more comfortable with those bare legs.

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The Shirt Under Everything Layer

Points For: Freshness

Why: It's one of those have-to-look-closely or you'll miss it details, but this shirt under everything layer is just so, so cool. It's a look you've gotta wear with confidence, but if you want to try it, please do. It's pretty awesome.

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