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And special thanks to Express for partnering with me on this post

Our favorite styles for black shoes with red dresses are classic black stilettos or black pumps that play up red's bombshell reputation

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Lace socks will become your loafers new best friend

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When he's not dressed in a dapper suit and freshly pressed collared shirt, the nomadic playboy-turned-lover-boy wears looser button-down shirts (don't forget to pop the collar) with some sort of layer on top, like a dark vest or brown suede jacket