Do you get catalogs? I get tons -- everything from LLBean and Lands End to Garnet Hill, JCrew, Banana Republic, Boden, Nordstrom, etc. Even if I get a catalog I've never heard of and have no intention of buying from, I like to look through it just to get ideas. One big thing to pay attention to is proportion -- like if you have a big flowy cardigan, you want slimmer pants. Or with flowy pants, a more tailored top (like all the cute jackets they're showing this fall!). In catalogs or on website, you can look for how to wear belts, like when a skinny one looks good and when a thicker one looks good.
If you find a store where you just love their aesthetic, love the pieces and how they put them together, request a catalog from the website. At stores like Loft or Banana Republic, I find the salespeople can be really helpful at helping you put an outfit together. When the new stuff comes in, they are usually taught what goes well together and ways to wear things.
Magazines are helpful as well. I like InStyle -- I don't dress like that, and certainly can't afford most of what they show, but again, that magazine is priceless for pointing out trends and how to wear things. Real Simple magazine has lots of good ideas, too, though also quite expensive. If that's not your reality (it's not mine), you can take their advice and apply it to great finds at H&M, Target, TJ Maxx, etc.
I used to watch the show "What Not To Wear." Frequently the makeover subject was a woman who had lost weight and didn't know how to dress her new bod. I don't know if it's still on, or if you can watch old episodes online, but that show was very helpful for teaching about silhouettes, proportion, etc.
I lost ~15 pounds and clothes that I bought on the way down are way too big now. It's good to wait until you are where you want to be, because it stinks to buy a great pair of skinny jeans and have to cinch them 9 pounds later. Skinny jeans were not meant to be cinched!
Fashion advice?
Even those are a bit big on me now.
