Best Bet: Black Out

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Photo: Courtesy of Ann Taylor

We can't seem to get enough little black dresses. Too much of a good thing is a great thing, which is why we love this new variation by Ann Taylor. This dress is built to flatter, with the neckline scooped just enough to offer a peek at your collarbone, without getting too showy with cleavage. The stretchy wool fabric is also elastic, so it highlights all your curves, but won't turn into a spandex cling-on. And the layered-ruffle sleeve detail adds a flirty element to the dark frock, which will help it stand out among the ten (or twenty) other LBDs hanging in your closet.

$165 at AnnTaylor.com.