Most of my cross dressers/sissys like humiliation so they don't mind (and want to) look silly...so to that end I have a bag with anything I have owned that has since gone crap. Stockings that have split or laddered, dresses gone bad in the wash. I'm a 14-16 so a lot of my stuff fit may of them anyway unless they are quite big, with the exception of bras because my back is small, but I have a few cast offs that I put 'half on' as in, without doing up. I also have cast off an poundland makeup. It all adds to the general silliness.
If a cross dresser actually wants to look nice they have to bring their own stuff or pay a supplement in deposit form for me to order what they want ready as I can't be expected to have any amount of man size female clothing for the odd one or two that show up intermittently, especially as these specialist items can be costly.