Shorts and a t-shirt, middle-age style

(Color is off on the first pic - baby turned some sort if filter on.)

As you can probably guess from this post's title, I'm not sure how I feel about this outfit.  The t is a little dressier than a plain t, and I like that it looks polished.  The shorts have a 5" inseam and cuffs which make them seem grown-up and modest.  But at the same time, I feel like both pieces age me.  I am middle aged, but should I dress it?

What do you think of this outfit?

(Top and shorts: White House black market, bracelet: Saks off fifth, a present from my little boy.  :) )