Great topic Mel! Mind if I jump in here.
When I first began losing weight my goal was to lose enough weight to be able to confidently wear clothes from Lands End or LLBean. I remember studying the mags and looking at them online for hints on how they would appear on my figure at nearly 190 pounds. Not great. As I began to lose the weight I realized that even if I was close to goal many of those clothes just would not flatter me for all kinds of reasons. Nice on other people, but not on me.
Last summer I spent almost every weekend shopping for clothes to fit my quickly changing body. No kidding, ask my mom, she was there with me just like when I was in elementary school shopping for beginning of the year clothes.

In fact in the spring of the year I spent two hours in the dressing room of Banana Republic with the manager and assistant manager trying to find a pair of pants that fit well or just a look/any look... The problem was that I'm a classic pear and the waists in these pants were huge! I purchased one pair but they still weren't quite right. But after two hours of their time I felt like I should buy
something. DH had a fit when he saw how much they gaped when I sat down in them.
It was such a challenge to not only learn how to dress this new shape I created but what exactly does a 38 year old mother wear?

So many new rules...and head games at play here. Like you had mentioned I dressed in ways to hide my bottom half. Long tunic tops, lots of jackets, things that probably just made me look heavier. Oh, and there were florals too. ~sigh~
After the Banana Republic fiasco I began to search online for clothing catalogs that may specialize in womens activewear. I stumbled across sites for
www.titlenine.com and
www.lucy.com Have you seen these? They are almost like magazines/catalogs where they give you a bio or story about their real life models who live very fit/active lives. AT LAST! Real women, my age or a little younger/older who looked great in these clothes. I used these mags as a guide. I would have loved to purchase many of their things but I still need to try everything on and these stores are a little further west than I travel on most weekends.
It was a little weird experimenting with a new style for myself. One of my first purchases, during a second trip to the mall, was a form fitting clingy t-shirt from Banana Republic. Fortunately, I had just purchased moments before a properly fitted bra from VS that is meant for the more sheer tops. I stood there in the dressing room blushing and thinking, damn this looks good I just don't think I can walk around looking like this. I mean ya know, is it okay? I bit the bullet and bought it. DH smiled at dinner when he saw me in it so I think it passed the test. I'm now smaller now than when I purchased the top so it's not quite so form fitting but its still my favorite for sentimental reasons. It was my official transitioning piece.
I'm still a work in progress though. My no brainer favorite thing to wear are my gym clothes because they fit well, look good, and no one is going to say "Did you see what she had on?!" "Isn't she too old for that?" To which I could reply, "What, you mean to exercise?"