Quite interesting to read such a mixture of reactions!

I, too, will have hard time parting way with some of my clothes. Mainly t-shirts that have really cool prints on them that have memories attached with them, but I've already thought to myself I can keep them and have them as lazy shirts or stuff I can sleep in! I never really bought nice dresses/skirts because I've never felt comfortable enough in them, so my wardrobe really does consist of t-shirts o_O.

But there's nothing like the feeling of going into a store and realising you need the size down =)

I know what you mean! I think a big part of it (for me) is that 95% of the time, I wear tshirts and jeans. Tshirts like, the kind you get at an event. Not like a cute one. So the cute/nice clothes I have are ones that I loved, that I think look great on me, and that I splurged on (because I hate clothes shopping). But now a lot of my stuff is starting to just look bad on me because it's so baggy. I was at the mall with my roommate and I just stopped and stared at my reflection in a mirror and was like, "I look worse than when I started!" because my baggy clothes looked awful. So I'm working on coming to terms with buying new stuff....but I haven't thrown anything out yet, either.