Most overweight people dread few things more than clothes shopping. When I was heavy, I would do anything to avoid entering a dressing room, with the three-way mirrors, the too-bright lighting, and the skinny salesgirls whose eyes seemed to carry so much judgment of my appearance. When you've been big for a long time, this dislike of shopping can be a hard thing to get over.
I first went clothes shopping for my new "thin" wardrobe before I'd lost a pound. You read that right. For me, so much of my weight problem was tied up in self esteem problems (and the feeling that I couldn't take any time for myself!) that I knew that conquering my fear of clothing stores, and starting to acquire a wardrobe of things I felt good in, was a hugely important first step. Think about how much emotion is wrapped up in your "fat pants," that one item of clothing that serves as a reminder of just how big you used to be, and by extension how far you have come.
Whether we like it or not, our clothes are an important part of how we present ourselves to the world, and how the world interacts with us. This doesn't mean you have to spend a fortune on new stuff, especially if you're still in the weight-loss phase. But you should make sure that your clothes make you feel good about yourself. Make it a goal to get rid of everything in your closet that you don't feel good in.
While we're on the subject, you should get rid of EVERYTHING in your closet that's too big. (You can keep one item from your heavier days as a talisman, but it should go with your keepsakes, not your clothes.) Weeding out your things this way will provide a symbolic break with your past, and will have the added effect of making it harder to go back to your old ways: if you put the weight back on, you'll need to buy all new clothes, again.
You may be tempted to have your old outfits altered to fit the new you. If the pieces are of good quality and not too out-of-fashion, this is a reasonable thing to look into, but keep in mind that having something tailored down more than a size or two is a major reconstruction job, not an alteration, and your tailor or dressmaker will charge you accordingly.
When you're ready to shop for new things, the process may feel very mysterious at first. I made some very weird choices my first shopping trip or two-- I had no idea what looked good, or even what size I was! Take along a friend who you trust, whose personal style you admire. And don't be afraid to carry a range of sizes into the dressing room with you. Just think how good it'll feel if you think you might be a 10 but it turns out you can get into a 6!
I'd love to hear your shopping stories. Share them in the comments!