I'm having mostly the same experience. I've always considered myself a bit odd because I enjoy wearing different "nice" clothes. When I was younger I struggled because, ironically, I HATE shopping. But then came the internet.

Anyway, the site is pretty cool because it opens my mind up to new ideas. But I had a lot of suggested outfits that were the same color of different pieces (no contrast as you said) and multiple jackets.

Wonder if it "learns" my style over time? I'd like to see this continue to grow. And maybe instead of the schedule feature, it could give me links to buy. I imagine monetization isn't far off if there's decent traffic.