My sims change daily but I don't use the dresser.
I select 5 outfits for each category. When selecting outfits in Plan Outfits I select one outfit that falls within the category then remove the filters so everything is available. I'll select one formal, one party, one athletic, one swimwear, one sleep, then 4 regular outfits in those categories. So my sims basically have 40 outfits to rotate through. My sims shower or bathe at night so I just click on the sim each morning and select an outfit for the day.