I don't have a huge numbers of items yet but I already know that, when I will, it's going to be a pain to go through the wardrobe. I wished it had more and faster ways to sort your items, like assigning the same item in more than one closet or search with keywords.

my answer to this is both yes and no...i build my HAs the same way as you where i pick one or two things i really want to use/new items i'm hyped about and try to build something off of that. sometimes i really enjoy the hunt through my wardrobe because i come across stuff i completely forgot i had. on the other hand, if i don't have an hour to sit and try to build, it gets frustrating because i have a lot of older items that don't really match the style of the site anymore that i'm keeping for achievement purposes, and i end up having to sift through all of that to try and find stuff that matches the newer site style for items. so really, it just depends how much time i have!

I often get SUPER overwhelmed trying to put together outfits these days with my big wardrobe. ;v;

I was just horrified trying to somehow remember where things were in layers and just adding mostly things that were most recently added to my wardrobe cuz chest layer would just be an endless maze that's for sure. Since I've been offline gonna need to study to recall what is actually in there. It's like opening a doom box and finding treasures you haven't seen in ages cuz you didn't remember you had them, and they're so buried in the closet x.x

But I also basically knew I wanted to use three items and play with that. Positive there's items I've never worn that I very much have wanted to ^^;

I hate having a large wardrobe. I occasionally think I’ll finally start working on HA achievements again and toss things back in there, but I’m annoyed by how long it takes to find them and get them back out. I emptied my wardrobe of over 10k items several years ago and sold everything. From then, I’ve limited it to pieces I find especially striking, that I’d build an outfit around, and the stuff I purchased along the way to go with those outfits.

I like to keep my wardrobe small (around 100ish items) mostly because my taste changes and I switch out items a lot. If I have an item I can’t seem to use, even if I think it’s really pretty, I’ll take it out of my wardrobe to sell or trade.

Yes and no - usually, I come up with an outfit when one or two items catch my eye that spark a good idea. The first step is then to look through my wardrobe to find other items which pair well with them - this is naturally easier done when my wardrobe is smaller (and containing only things I really, really like). In a second step however, I usually sift through the entire list of clothing items (for some categories - e.g. background, head, etc. - at least) and try to search for appropriate keywords in the items' names to fit a certain theme. This part is the most important for me as I normally have a very specific outfit idea in my head and therefore only very specific items will work. I usually do not own the majority of items which I need for my outfit at the time I am creating it, so a big or small wardrobe makes little difference for me. Overall, I'd say that my wardrobe is not overly large - less than 2k items - so it's manageable enough.