“Whether in the boardroom or a cocktail party in the Hamptons, always keep it preppy and cool,” says designer Tommy Hilfiger. “Pairing a gingham shirt and tie with a solid navy suit allows the shirt to pop in just the right way.” Thomas Pink executive Simon Maloney says: “Gingham shirts work well with a variety of tie styles—straight ties, bow ties, skinny and knit ties. Feel free to experiment.” Tommy Hilfiger shirt, $68; J. Crew tie, $60;
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