Best Bet: Babaton Anton Dress

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Finding a dress that pulls double duty for casual dates and more formal affairs is usually impossible, but this flirty number from Aritzia fits the bill. The A-line silhouette flares away from the body, flattering all figures, while the delicate lace adds levity. As an added bonus, when you turn around the semi-sheer back adds a dose of sex appeal. Pair with flat sandals for a date-night look that feels effortless, and then add sharp stilettos for an easy go-to wedding-guest outfit.

Babaton Anton dress, $140 at Aritzia