I sorta have the male version of your wardrobe issues in your post, "Femininity and Weight." It manifests itself in the form of business suits. When I am at the low end of my dieting range, I reward myself by buying nice tailored suits (I have to because my shoulders are broad and the standard 10-size drop doesn't fit). When I am at my fattest I have to buy tailored suits because suits of that size are only available in nicer men's shops. But in my middle range (where I live most of the time) I can buy suits off the rack, usually not very nice ones, but cheap and they look like they are proud of it.
So I spend my life in cheap, ill fitting suits... Sigh. Fortunately I don't wear them nearly so often these days as industry has, in the US at least become more casual.
Height: 5' 10"
Starting Weight: 292
Starting Primal Weight: 275
Current weight: 240
Goal weight: 172
Body Fat 31.1