I've been taking at least 5-10 things out daily - whether it's a simple piece of junk mail to a piece of clothing that's being donated - so that's seemed to work out fine for me. I gave a pair of Chuck T's I'd gotten a couple of years ago that (while cute and comfortable if I was just standing still) were perfectly horrible the first few times on my toes, to my daughter. I'd replaced them with a pair of hi top versions in a half size bigger which are much better.
I also realized that these days, I'm more about comfort than glamour, so I sized down most of my high heeled shoes (I kept a few pair in the universal colors - black and natural/tan). I mostly wear boots and sneakers in the fall/winter and sneakers and sandals in the spring/summer so I have my essentials pretty much set. I did however, go online to DSW this morning and using two rewards certs I had (I didn't even KNOW I had them - apparently they were sitting there since I did back to school shopping in August and were about to expire) with a gift certificate and got a couple new pairs of Chuck's and Keds for the summer. I think I'm going to revisit my shoes again though, just to be sure there isn't anything there I missed.
Honestly, the LIWI challenge WAS a bit challenging for me. I was at my SO's house over the weekend, and I looked at the clothes I have over at his place, and realized I wear everything there so I didn't even consider them. My wardrobe at home is probably equivalent to what I have over at his place, with the exception of lots of T-shirts and tank tops which I live in during the summer. What I tend to do with those T shirts I get tired of wearing out, or have just faded a bit and may be a bit threadbare but still in good/wearable condition, is wear them either to bed or around the house as my "house clothes". I grew up in a household where that was common: we had our "outside clothes" and when we got home, we'd change into our lounging/house clothes. These days, it's more about just getting out of clothes I've been in all day, and slipping on something warmer and cozier during the colder months, or something looser and flowing that aren't clinging to me during the warmer/hotter months, but they are still wearable for a quick trip to the store. Once they become slightly threadbare, out they go.
I want to whittle down my closet just a bit more, even though I have minimal as it is. I think I will tackle that once I get home today. My purchases are still minimal - so I've kept it very simple with spending. I'm always on board with simplifying more, though.