Loving this thread so much! Im leaving for a several months long road trip in one week, so I have streamlined my wardrobe because, besides a small storage unit, if it doesn't fit in he Honda Fit, I'm not keeping it.
This process has been so much fun! I got rid of bags and bags of clothes and shoes that I never wore, and I've organized my remaining clothes into A-team, B-team, and C-team.
A-team clothes are going in one carry on bag. These are the items that I wear all the time. Lately my uniform has been tunic + crazy leggings + Chaco sandals so that's all mostly filling up the first carry on, along with 2 pairs of jeans and 5-ish tops, pjs, and a week's worth of underwear.
B-team clothes are in my second carry-on size bag. These are clothes that I will need when it gets chillier or if I need to dress up for some reason or if I run out of underwear :)
C-team clothes are in one of those Rubbermaid plastic bins and include a fancy coat, some more tops and skirts, and some sweaters. I may end up bringing this bin or I may end up putting it in our storage unit ...
Finally I have one more bin that is mostly sentimental clothes -- my wedding dress, an awesome fancy Hawaiian maxi dress, my threadbare Ramones t-shirt from back in the day -- things I don't wear but still want to keep.
So I'm down to 2 carry ons and 2 bins. It is a FANTASTIC feeling.
And we are doing this with everything -- kitchen stuff, hobby stuff, everything. Every load of crap I take makes me feel happier. Our apartment is looking rather empty and both my husband and I are like "the less stuff we have in here, the more I like it!" Good thing to know for when we settle down in future ...