Originally an offspring of the white spats worn by gentlemen in the 1800's, spectators hit their peak in the late 1920's and 1930's. They were a sporting shoe worn on the golf course or to the race track, hence the dark leather being on the outside to protect the toe and heels from dirt, grime and grass. Since the swing revival of the 1990's, spectators have taken on a connection with swing, jazz and the gangsters that symbolize the Roaring Twenties to most people.

Spring and summer is the perfect time to break out the spectator (or pick some up for the first time). The white leather is perfect with the lighter colors worn in summer, or to add a little air of insouciance to a sharp suit. White and black or white and brown are the two most common colors, but you can find just about any colors if you look hard enough. Remix Vintage Shoes and Magnoli Clothiers are two great sources for spectators, with the former being popular with Johnny Depp. The latter offers several styles and colors with some models being made on a custom basis.
My best advice for matching spectators with your outfit is to treat the shoe as if the white leather did not exist. So if you have a brown and white spectator, treat it as you would a brown shoe. White in other parts of your outfit are unnecessary. Try out the look of a great pair of spectators with a silk camp shirt and linen trousers. Or take a page from Archie Goodwin (via A&E's Nero Wolfe Mysteries), and add a dapper touch to your suit for the office. A word of warning. One can quickly get noticed wearing spectators! These days, wearing spectators past the warmer months is acceptable, but the slush of winter has killed more than one pair of these classics.
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