Thank you thank you thank you everyone for your words of wisdom and reassurance! I hope you all don't think I'm a whiner or navel-gazer for starting this thread. I was just inspired by Angie and Mochi and everyone else's minimal wardrobe threads and feeling a little frustrated that I didn't know how to achieve it myself. But I realize now that I don't really need to have a minimal wardrobe, I can have a large wardrobe as long as it's functional and organized and I wear everything. I would love to have a mix and match wardrobe like Sveta's but right now I don't think it's achievable for me.
I still would like it to be a little smaller, just because I feel like I am not able to wear my favorites as often as I'd like without neglecting everything else. I LOVE Angie's dictum above to "WEAR YOUR STUFF" because it's so true! I need to repeat this mantra over and over! (I'm so glad I started this thread just for that...it's like going to the top of the mountain and hearing the guru speak!) My favorite pieces I typically wear 2-4 times a month, but other things I may wear only once every 2-6 months. I guess I have to decide if that is often enough for me to justify keeping. I wish I had read some of these small wardrobe threads back when I was first starting to accumulate. Because like Diana, I tend to hold onto things for a long time...once I fall in love with something and it passes my K/R, I tend to always like it, even if the fashion world has already moved on. I think my "dated" filter is a bit defective, LOL! (I still even kept a couple of those 90's skirts!). It's so much easier to not buy something new than it is to purge something that's already in your closet, especially if it's relatively new and fits well and already works with your style persona.
I did get rid of a lot of stuff for the OC YLF swap (some of it was even post-YLF purchases). I will definitely try to keep purging regularly, but I think the key for me for decreasing wardrobe size will be to avoid shopping temptation and make more thoughtful purchases. It's easy to get carried away and duplicate favorite silhouettes or colors (my dress collection seems to multiply like rabbits!). I have to remind myself to only buy things that are a true wardrobe hole that actually needs to be filled, and not get seduced by something that is cute and fits and is "so me", if I already have similar items.
I think another test question that I need to keep repeating when I consider a purchase is "Would I rather wear this, or my favorite dress/shirt/skirt etc. more often?" If I like my favorites better, then I need to stick with those! To that point, I recently was browsing the Anthro website and found all these cute dresses on sale (some of which I had considered ordering when they were full price) and filled my cart with a bunch of them, each in multiple sizes. Well, I ended up deciding not to hit "buy" yet and think about it for a day or two. And now, I decided I don't really need those items as I have others that would work just as well. So, that is real progress for me! Old me would have just bought everything and tried it all on and returned most of it. Much less work for me not to buy anything in the first place! It's just as well, because I'm getting kind of fatigued with shopping and the whole order/try on/return cycle. It's nice to be able to just shop my own closet instead!
I was so inspired by the wisdom on this thread that I spent over an hour working on my closet tonight--hanging everything up that I had tossed on the floor this week, going through everything and pulling a few things for swap/donation, and setting aside my whole jeans collection that doesn't fit me anymore (around 20 pairs, yikes!) I'm saving them in case I can make it back down to my original weight, but it was such a relief to clear them all out of my closet...I felt like I could breathe a little easier! Having them there and wondering whether I could still fit into them was stressful! I realized that I haven't worn my colored denim (except the red) all that much, so maybe next time those will be the first to go. I do have the boyfriend jeans and larger sized jeans so I do have a few pairs that I can still wear. I think I'll be OK. I also culled a bunch of T-shirts that I rarely wear because they're a little too tight/short now and a few other items that I wasn't excited to wear. I'm going to put them all in a holding pile and re-evaluate them later when I have more time.
So, long-winded response to say that I took all of your advice and applied it to my closet and while it's still large by any measure, I feel like I made a lot of progress in streamlining it as much as I can! Thanks for your support--I really enjoyed reading your responses!