For centuries, our clothing has reflected status, not age. It may seem as if we have moved past a class- or occupation-based dress code in our society, but that’s only true for young people, hence your confusion. When adults forget they are fully grown, they often dress inappropriately.

Consider the great Sir Walter Raleigh, whose jewel-encrusted boots had such high heels that he could not walk on cobblestones. Unless you are under 22, such outrageous style is reserved only for the wealthiest English knights, as demonstrated most visibly today by Sir Elton John. 

   Sir Walter Raleigh, at c.33

A black skull t-shirt is allowed for adults, such as bikers, and many artists and musicians believe it lends them a sort of macho credibility.  If you are a banker, engineer, or marketing consultant, however, your days of skull shirts most likely should be behind you.

   David Evans, aka The Edge, at 46

To be safe, which is usually easiest, dress like your friends and coworkers (or potential coworkers) and do not deviate from their style. Flatter them by asking where they shop, and give up on being creative. If you have no friends or coworkers, and want to look like you never need to exert yourself, try flip-flops with a polo shirt.

—Shallow Sage

(Click the “Ask” button for our Sage Advice)