Best Bet: Jill Jill Stuart Long-Sleeved Lace Dress

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Finding a dress that will take you from date night to fall weddings and well into the holiday season can be tricky, but this lacy number by Jill Jill Stuart fits the bill perfectly. An illusion neckline adds subtle sex appeal and the long sleeves mean you won't be shivering in the chilly air. The rich navy hue and festive lace feels classic, but will still stand out among the sea of black dresses. Wear it with black heels and dangly, sparkly earrings, then you're good to go.

Jill Jill Stuart long sleeve lace dress, $288 at Shopbop.

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