I think the hardest item to box was a pair of size 14 Silver jeans. These were "reward jeans" from many years ago when I'd lost about 1/2 of the 50 pounds I eventually lost and they've been folded up on the top shelf of my closet for years. I'd been in an 18 and treated myself to these $80 jeans when I'd lost about 20 or 25 pounds. I'm back comfortably into my 8s and even a couple (vanity) 6s but I have at least 10 pounds to go. I doubt my size will change much more with another 5-10 pounds but you never know.
Those are my 8s on top. Puts into perspective how far I've come (and I wish I'd saved a pair of 18s for comparison). I will never wear a size 14 again and it was time to say "good-bye". Closure. Or "clothes-ure" as the case may be.