Focus on your underwear. I'm telling you, if you can have smooth, firm lines, you'll feel good in just about anything. Invest in some good shapewear--panty girdles, supportive (but pretty) bras that cover back rolls, something to hold those thighs still in a sexy pair of capris.... Girl, your options are limitless. Don't feel intimidated by other women who look great in their clothes. They are wearing shapewear, too!
Once you get over that hump, go to a high-end department store and plan to invest in a couple of staple pieces, but try on EVERYTHING. (At the high-end stores, they cater to women who want to polish what they see as flaws. AND you have more choice of quality and classic pieces. Trendy looks okay on the itty-bitties, but not so good on larger sizes. It also doesn't wear well.) Let the shopper know that you are working on your style. Do NOT gawk at or complain about the prices. Just buy what you want (at least two pieces to make it worth her while). Nordstrom carries Not Your Daughter's Jeans, and I love them since I just had a baby. They do wonders for my self-esteem. Walk into the boutique that you've been passing every day, the one with the stuff in the window that you slobber over but wouldn't dare try on. Go in there and tell that owner that you are looking to change/improve your style, that you want to venture outside of your comfort zone. Get the ball rolling by wearing something (flattering) that you wouldn't have imagined--drastic haircut, bold nail polish or earrings or bracelets. Get a toe ring or an ankle bracelet, to show off on your trip. That'll feel sexy.
Start now with good eating habits (if you're not doing that already) and keep your bowels moving EVERY DAY. You've noticed the difference when you've emptied it all out. I know that I feel light and sexy. And more comfortable. Confidence is key here. Enjoy!