One of the biggest challenges I came into was that of getting new clothes that fit right. For a while I would wear my old dress shirts and kakis and they were enormous on me after losing the weight. So I would go to the store and pick out a new shirt and pants, pay the money for my new outfit. and in 2-3 moths they would be too big again. Its a great problem to have, don't get me wrong, but it can get pretty costly to always be adding now clothes to your wardrobe and always be throwing out the old. Even now I still wear dress shirts to work that are too big and frumpy on me because It just is not possible to go out and totally re-buy a whole new wardrobe in one day. And when you wear frumpy clothes, you feel frumpy. Its hard to fully enjoys the weight loss when it gets so pricey.
I do however refuse to wear the novelty t-shirts both those two stores sell. I am sorry, but I left the days of wearing shirts with cereal brand names in Junior High where they belong.