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In the old days people were expected to wear specific things for specific tasks or gatherings i.e. business suit, dinner jacket, etc. That took the guesswork out for folks who didn't want to be preoccupied thinking about dressing. Now those days are gone but nevertheless some basic things worth having are as follows. A plain suit that can be worn with a pressed shirt & tie, a non matching but harmonious sports coat & pants & a couple of decent looking shirts that go well with them. If a sense for good color combinations is not something that comes naturally one can refer to vintage movies, catalogues, etc for inspiration.