I did. Like you kept some but looking through them I realised I would never wear most of ghem, even if I lost weight. I lost 50lbs last year and it was great to try on the remaining clothes but out of a wardrobe full, I was left with 3 or 4 things I would actually wear. I felt like it took a pile of pressure off.
I just joined Ww this week and am embarrassed to admit that I have 10 80l storage boxes of clothes that don't fit. DH and I are this week moving them to the garage and out of the spare room. I have a special event happening at Xmas so am determined that whatever I don't fit into by then, will be going. It is one of those events where there will be photos forever and I have mentally accepted if I don't do it now, I will never do it. On the plus side, most of it is fantastic stuff from Next etc which I purchased for very little from charity shops and it means I will have a complete wardrobe in every size as I go down.
I jettison anything that doesn't fit and anything that wasn't worn at all in the last season (so if I didn't wear a summer item at all that summer, and summer's now over it goes- we have very clearly defined seasons where I live ). I've regretted it maybe once.
Also agree with fashions moving on- I kept jeans I wore pre-first pregnancy and by the time I got back into them post second pregnancy (only 3 years in total) they looked so dated.
I've sold all of my clothes that are a size too small on eBay, I've made a lot of money as it appears to be a brand people love and I've reinvested the money in clothes a size up and a style that suits me. Now when I open my wardrobe I see clothes that are beautiful, fit me and don't make me mad with myself for not losing that extra stone and a half! I've not missed anything I've sold as yet!