I divide my clothes into strata — decorating, gardening, kicking around the house, shopping, meeting friends, formal — and wear whatever I find first from the stratum I need. I have several similar-looking shirts, so I make sure that today's shirt doesn't look too similar to yesterday's, so that no one thinks I rewear them without laundering them.
Jeans and sweatshirts do get reworn. As a result, I'll have two or sometimes three on the go at once. My bedside chair is a mess.
Demoting clothes to a lower stratum when they're no longer pristine always feels profligate. And I have far more decorating shirts than I need, given how little decorating I do!