Funny you should ask, because that is how I spent my day today. I went through my 'city home' closet (boyfriend's place downtown, where I keep the bulk of my wardrobe). Two items that I am purging are a vintage Versace dress, and a gorgeous black lace Lew Magram dress, because they are both too big, and would require extensive alterations now that I have lost weight. Boy was that hard! They are both awesome dresses.
I offered to send them to my taller little sister, but with the
stipulation that if she doesn't like them, to give them back so I can
put them on the auction block
I also purged a Missoni dress and a tube/halter sweater that I'm going to put on eBay. The tube is part of a twinset, really, but I can't quite bring myself to part with the cardigan just yet - despite almost never wearing it.
'Breaking up' with a piece I really like, but never wear, is strangely hard to do, until I remind myself that if I save up enough money, I can go for something really high-end that I will love and use, down the road.
One thing that made all of this easier, was, every time I wavered and thought, 'maybe I can make this work somehow', I would just put on a dress or skirt and top that really fit well, and remember that these are the things I need to be wearing, not the designer dress that makes me look like Charlie Chaplin.