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Shop Now at This dress shoe has an excellently cushioned footbed which provides you unsurpassed levels of comfort all day long

Satin, and other formal fabrics, will wilt in hot tropical weather, cotton can be tricky to keep crisp and neat, so stick with highly-packable fabric like a light chiffon, or dressy maracaine jersey

For example, a pair of black Docs feels a touch more aggressive than a pair of brown Red Wing boots, so you might wear the former to a dive bar (see: Ryan Goslings bro-friendly look above) and the latter on a date

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More commonly known as black-tie optional, the idea is that while you dont have to wear a tuxedo, you still want to dress nicely enough to be considered formal