Off-season clothes are tough!
Pants are the WORST.
Blouses and tight sleeves that don't stretch are pretty much out of the question. If you have to wear business suits for work, good luck to ya!
Dressing up for parties can be really tough
I'm still relatively "small" during the off-season (although big for me), meaning that I can manage to fit into a size 6 or 8...but I still have the same problems because of my overall shape. I put a courderoy coat on two winters ago, and when I went to pull my arms all the way through the sleeves, I split the seam down the back.
Getting a pair of pants to fit in the legs usually means they are too big in the waist. Getting a pair of pants to fit in the waist usually means they look like they were painted on my thighs and ass, assuming I can even get them on.
I have the best luck with jeans from the Gap actually. I buy the stretch flares or whatever that style is. I'm sure there are better options that I don't know about, but stretch seems to work the best.
I've been wondering what other fbbs do because it can be very frustrating...esp when you are running late to work and cannot find one fkn thing in your closet that fits right that day!