Organizing my closet

I am working through the Organizing my Life/Mind workbook. I am always working towards losing weight and have many items of clothes that I haven’t fit into for years and years. However, I keep hope alive as I work on myself using the scholars tools. I am less than 2 months in to scholars. Some of the clothes are nothing special but I would wear them if they fit. When I go to organize/declutter, I haven’t let them go. I have plenty of space in my house but they have been there unused for years. I could also afford to buy new shirts if they do ever fit again. Saying goodbye to items is work so does that mean I could benefit more from getting rid of these things rather than tuck them away? What to do?