Great thread, very interesting suggestions. Glad to see it's helping you, Staysfit!

I do tend to plan ahead, albeit in a rather ad-hoc kind of way. My strategy is to build a few seasonal capsules around particular activities, and reach for them depending on the weather, mode of transport etc. This generally leads to a number of outfit formulas which can be mixed and matched around particular garments. Like Ginger I'm quite emotional about it, so even if I have tomorrow's plan in mind when I go to bed, it might change completely when I wake up. That's OK. And like Suz, I plan travel capsules with military precision.

I should add that one of my key YLF learnings has been limiting the colour palette and setting rules around it. I've found this helps enormously in building cohesive outfit capsules that feel just right, but it's led me to adopt a mostly neutral palette of black, white and navy blue. You obviously love colour so perhaps you could enlist the help of your talented daughter in building a few awesome colour combinations (you're probably doing that already).

All that said, I still recognise the problem. I think there will always be days when I need to change my shoes three times before leaving the house.

Having tried both planning a week at a time and night before, the night before approach works best. If try ons are needed, that is best done on the weekend for me. Now I try to try on possible outfits as soon as I get something new to know what works together. This used to be written down in a notebook, but now I mostly keep it in my head or take photos.
To get around the emotional dressing, it helps to work into the plan a variation of silhouettes, colors and formality.
The flylady plan of laying or hanging everything out the night before really helps to get moving. It also eliminates searching for something that might be in the laundry or the bottom of the scarf box.

I have been coming up with running a list of items I want to wear and just refining it, usually the night before, into what I want to wear the next day. I don't lay anything out, as there's not much space to do so in my place (or my cats would park themselves on it).

I have had some wardrobe turnover and have been trying new styles, so I'm not sure how I want to style everything. I end up usually going with a top, cardigan (if the top isn't warm enough for my office) and pants/jeans rather than anything trickier involving pairing jackets and tops, etc. I don't leave myself a lot of time in the mornings so I can't experiment. I have yet to figure out how to deal with that problem.

A little bit late to this very interesting thread!

I usually mentally put my outfit together during my morning shower. Centered around one favorite piece, and the rest to go with it. I also noted the outfit, on an Excel spreadsheet at work. Very illuminating over time. Helped me to remember what outfits or individual items did not add happiness, and which were super combinations (as well as tracking wears).

I am not a big accessories person in terms of a lot of jewelry choices or shoe styles. I usually wore the exact same earrings and necklace (simple gold chain w/heart) every day, and the same style of shoe (if not the exact same shoe) every day. Plus I keep a bit of a limited color palette, and I do try, when shopping, to make sure new things will "go" with other things.

I did try to spend time with new purchases to try out combinations in advance - after work, while still wearing the proper undergarments & stockings, or right when I brought the new items home

I also tend to be a bit obsessive over a few items at any one time, so those would get high rotation, and I never care about repeating! I did catch myself repeating my casual Friday outfits a lot!

But of course there would be mornings of frustration, especially when introducing a new piece or combination. I only had a little bit of time to goof around with changes, and sometimes had to shrug my shoulders and mentally tough it out for the day. I've had plenty of "fails!"