I repeat pretty often for daily wear - or I repeat the basic "uniform" if not the exact items. I tend to have a smaller group or capsule of current favorites on rotation most of the time and then after a couple of weeks or so I might change up some of the items. I tend to wear denim shorts in blue or white and khaki shorts quite often in summer and have only recently been trying to buy different styles of those to change things up (like a shorter denim short that cannot be rolled in a darker shade or a slimmer fitting short in an almost cream colored khaki).
For going out I do like to wear something a bit different if I can because like many here I don't go out dressy very often at all. Dressy for me in summer might be just patterned shorts, a silk top and nice sandals.
