Just because you’re comfortable doesn’t mean you’re a slob.
It’s almost illegal not to wear shorts in San Diego. Unfortunately, most guys do not pull them off well.
Preserve your style by wearing shorts that fit perfectly, are in a conservative color, and are paired with nice stuff that compensates for how casual your legs are.
I recommend wearing flat-front, slim-fit chino shorts. They’re as formal as shorts come. Wear them anywhere the ground isn’t made of sand.
Athletic shorts are the norm. Nobody other than me will care if you wear them, but chinos will make more of an impression.
Fit is the most important consideration. They should stop about 2” above your knee. They should also be slim enough to show the contour of your thigh. The leg opening should be narrow.
Resist the temptation to pick “fun” shorts. “Fun” equals “childlike.” Shorts are only a degree or two removed from underwear, so don’t push them even further in that direction with unusual visual profiles.
Tan and navy blue are the two best color options. Black, gray, brown, olive green, light blue, maroon, and white are acceptable.
Avoid patterns and prints. You want a single, solid color. Stripes, dots, and little pictures of lobsters make you look too boyish.
Wear shorts with a polo shirt or a casual button-down. Closed-toe shoes are better than flip-flops. Think classier sneakers and boat shoes. If you’re going to tuck your shirt in or wear more formal shoes like loafers, just wear long pants. At that point, it’s weird that we’re looking at your business casual shins.
Consider buying shorts from thrift stores. You can expect to pay between $5-8 per pair. New, they’re around $20 on the cheap end.