I kicked off spring cleaning today with putting away the Winter clothes and purging my wardrobe. Among other things I gave away 20 pairs of jeans. I have not worn any of them since I moved to NC. They are way too hot to wear in Summer, not warm enough to wear in Winter and overall terribly uncomfortable. The older I get the more I pick my clothes by whether they are soft and comfortable or not. I only kept one old well worn pair.
The old advice that 'if you have not worn it in a year you'll probably not wear it again' is true unless it is some special occasion outfit, and I would add to that not to keep any clothes that don't fit just in case you lose enough wait to fit into them again. Instead, if you do lose weight, reward yourself with some new pieces (don't have to be brand new, thrift store finds will do nicely). The closets in this house are very small and I am proud to report that my entire wardrobe fits into mine.