I'm also a repeat offender but I try hard not to repeat the same outfit with the same crowd/occasion. Since I don't go into the office every day, this is fairly easy. With a lot of our social occasions we will run into the same people over and over, so I try not to repeat there either.
I love taking photos and keeping track of when I wore what - because then I know not to repeat, and can also go back through the photos and recycle outfits when I'm at a loss and not feeling creative.... which is probably half my days!
Of course, when Jean came over last week, I had to step it up and find something new from my closet, because I figured she'd seen it all!! That was hard, but also fun.
I suspect I'd be less creative if I had to go into the office every day. Realistically, I would prefer to sleep in a few extra minutes rather than spend it getting dressed in the morning! I did think about that recently, with this new job there was a possibility my new boss would expect me in the office more. When I used to work in an office daily, I was a creature of routine and repeated all the time. Just like I do with my cooking (if it's Monday it's pasta night, yep). So I figured if I had to go back to the daily office grind, I would put myself on a schedule: I have 5 short-sleeve jackets, I would wear one each day, with a different blouse and different jeans each day. I figured that would give me the necessary routine plus a little bit of creativity to mix it up.
I do not think there's anything wrong with repeating. I really love having "no-fail" outfits to reach for on those days I'm just not up to the creative effort or don't have the time.
