I've been buying LOTS of knits... wrap dresses (which are wonderful when losing weight), structured pencil skirts, draped cardigans, heavy jersey pants. Much more forgiving as I am buying with no forgiveness at first (so it's "gain a pound, it won't fit") and then losing gives me give room.
A good tailor is great... many things can be minorly taken in.
The one thing that's been killing me has been jeans... but I've found a style at The Gap that I like. I buy them in the size I am at the moment where they are almost too tight to button - jeans today have stretch so that's actually the right size once you've worn them an hour or so - and when the start to get loose, I buy the next smallest size... the bigger ones become more of a "boyfriend jean" (which is stylish right now) while the tighter ones have the skinny fit.
I've also got a couple of great friends who will grab me when my clothes look too big and say "don't wear that again"... I've gotten rid of a lot of stuff out of my closet recently.
