I don't have much of an emotional attachment to clothes, none of it really means anything to me. The things I feel reluctant to let go of tend to be things I don't feel I've got enough wear from. As an example I have a pale blue suede jacket that I've worn once before I outgrew it. It is very fitted, and looks odd now that it's too big, but it cost sooo much money and it's been worn once. I'm embarrassed that I spent money on something so impractical, even more so that I then never used it and wasted the money. It's not about the jacket, it's about the wastefulness, if that makes sense.
Still, come January it will go, because hanging onto it doesn't make it any less wasteful!
When I lost weight last time I had a few jackets altered by different tailors, but when they re-set the sleeves they never quite look right, otherwise I'd take this jacket and my more expensive suits to have them altered.
My only consolation is that at least in the new year I'll be able to buy relatively cheap work suits rather than having to pay hundreds of pounds - it could always be worse!