I'm curious: What, to you, makes an outfit successful?
For me, I am most happy when three things come together: physical comfort, appropriateness, and having my style goals met.
First, I can't be happy unless the outfit is comfortable - no need for pulling on my clothes, constant adjustments, or, god forbid, bandages (yes, it's happened).
Secondly, the outfit must be appropriate. I like to wear clothes with the right level of dressiness and that have the right vibe for the occasion. I do not like to be over or under dressed, or dressed incorrectly for the season (plays in to being physically comfortable as well). Of course, my definition of appropriate isn't universal, and that's OK. I guess this is a little bit of an art but very important to get right in order for me to feel my best.
Lastly, I need my successful outfits to feel like "me". The right mix of trendy, feminine, classic, and - I'll admit it - weird. Boho and "hard edge" items don't fit that well in my style although I can mix it in if it's balanced enough. My hard edge ends up looking a little more Goth or Victorian (but very, very, very toned down, mind you). My boho always leans heavily towards pretty, classic or even downright preppy.
I'm curious to hear what other's thoughts are!