Seven years later, shorts and T-shirt is about as normal as it gets. Flip flops or old running shoes for footwear, depending on weather conditions.
There are very few occasions in my life where I need to put on “nicer” clothes outside of work. If that the case then it’s a polo or button down with chinos.
If you are fit, lift a little and wear some reasonably decently looking higher quality shorts (not ragged cargo shorts from Old navy) then I personally don’t think the look is too sloppy or unattractive. Others might not feel the same.
I guess my last point there is that you can take two dudes wearing basically the same thing, but look completely different. Shorts (not athletic shorts), tshirt (well fitting and simple) and running shoes can look clean. But if course we’ve all seen the fat slob at the grocery store wearing old, stretched out gym shorts and some crappy looking graphic T-shirt. Not a great look. But that’s his problem. Not mine. Wear what you like. Because America.