I'm not going to be much help because I'm either working from home, on a business trip, or out and about seeing different people at various leisure time activities.
The only time I worry about repeating is when I travel, and in that case, deliberate repeating via remix is the very goal, since I want to pack light. So I might bring one jacket, one cardigan, one or two pairs of pants, one dress, a couple of blouses, two pairs of shoes -- then remix.
I will say that after returning from a trip, I've grown sick of the items I packed, and need a break from them for awhile. So I do need variety but I also dislike keeping to a rigid schedule or plan.
When I was all into dresses awhile back, I did rotate, this is Monday dress, this is Tuesday dress, etc. A black or navy dress could be worn more than once, with change up of cardigan, shoes and accessories.
Okay actually I also worry about repeating for special occasions. I do frequently go back through FB & WiW photos to see what I wore the year before to an event, and try to wear something different, so I don't look the same in photos. I don't think anyone at these events would ever remember what I wore the year before, it's more for the photos.
I repeat a lot on Sunday's -- my most casual day of the week -- because casual is not really my style. That said I am repeating less lately as I'm easing into casual more and more.
I also repeat quite heavily in the summer months, because summer is quite short here, and I find my summer capsule clothes don't last all that long because you sweat through them, they pill, they fade, they get sunscreen all over, etc. I deliberately don't invest as much $ in summer clothes. I just refreshed my summer capsule via ON - a couple of maxi dresses, a shift dress, some tees, a maxi skirt and that's all I really need.
I guess I am a repeater more than not, as when I find an outfit combo I love I do wear it over and over again -- which is why you don't see me posts WiW's every day. Due to necessity of tall boots to navigate snow piles around here, I've currently got maybe 4-5 "go-to" outfits I am rotating. I've got no problem with that, and usually find I get bored right around the time the weather shifts, opening up my options.