Let me first say that you don't look miserable in photo 6; you look spectacular in each no-repeat day. I also love the cranberry/burgundy top on you and am smitten with the all-black outfit, too. Speaking of leather jackets, I can't tell you how often I grab that Danier jacket and feel good every time it's on me.
Now, I need you to explain all of this to me; I don't even understand what you mean when you have "only three dress in rotation." Or, sweaters and shirts "in current rotation." Are these seasonal items and only used, say, in colder weather? So, are the dresses being "repeated" or not part of the "no repeat" challenge?
Too many questions and you don't have to answer them, but I think it's just a matter of not repeating and having your pre-arranged line-up of clothing that will get you through.
Suz, I think you really got to the point of it when you mentioned that it was the silhouette of an outfit that added to the challenge. I found that out a day or two ago, when I jumped into my skinnies and knee-high boots and, while it was easy, it wasn't very exciting for me. How to add that ease of dressing and excitement together is my current challenge.