I wish. The only real outfit planning I do is either the night before or for an upcoming special event.
3. Do you have any specific ways of tracking outfits and items already worn so you don't repeat?
If it's on the floor or in the laundry, I've probably worn it recently. I can usually remember complete outfits that I've worn and will only wear it again the exact same way if I think it is worth repeating.
4. How do you discover new combinations of items in your closet? (Trial try-ons? Hanging items together?)
I hang items together, but it really doesn't matter until I try it all on. I tend to imagine myself about 6" taller with smaller boobs and a longer torso, so things always look different on my real-life 5'4", curvy bod. I think I'm getting better at visualizing my clothes, but it's definitely an acquired skill for me.
5. To streamline the process for 2011 what is one new thing you can do to cut down your dressing time?
Write ideas down instead of storing them in my brain where they're forgotten. I'm really good at taking notes and making lists, but really bad at referring back to them.
Also...and hate to say it...but ironing in the morning is a real time-suck. If I would only get off the couch and DO IT the night before...
Shirt: Ralph Lauren, thrifted
Dress: Converse, hand-me-down from Elaina
Shoes: Seychelles via Amazon.com