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With a princess cut, this fully-lined short cocktail dress has a sheer overlay with beaded and sequined floral details that shine for homecoming, fancy dinner parties, and sweet-16 events

[18] If you want to soften the look slightly, a pastel pink shirt paired with a navy or purple tie warms the grey without losing polish -- a pairing with a long track record in classic menswear

While the sleek jeans you styled for a casual dinner can be considered acceptable in certain business settings, focus on chic pants to err on the side of caution

Floral Maxi Dress With Ankle Boots A floral maxi dress feels like a garden in motion, and pairing it with ankle boots gives the look an unexpected modern edge