If you’re planning a trip to the racetrack for the first time, you may be asking yourself what exactly you should wear. It’s always embarrassing to arrive somewhere and realize that you’re either completely over- or under-dressed. Pop culture sends us mixed signals: either you're supposed to dress like Eliza Doolittle heading to Ascot in “My Fair Lady” or you have to look like an extra in “St. Vincent.” There is no in between.