I lost 2 stone a few years ago, deliberately, not through illness and I have kept it off. I have never had vast quantities of clothes, but I really enjoyed getting rid of all the oversized clothes and replacing them with clothes 2 sizes smaller. One or two garments did stay wearable; a winter coat and a couple of sweaters but everything else from underwear up had to be replaced and the local Charity shop was grateful for my discards.
Any regrets? yes, a lovely long grey wool winter coat, it absolutely swamped me after the weight loss. I gave it to DDiL, who is much taller than me and proportionately wider. DGD (aged 9) has told me that everyone says how nice her mummy looks in the coat. I have been unable to replace it, even three years later, but it was unwearable and the problem was the fit on the shoulders so not really alterable.