For me, it was a big help that I had kept a lot of my clothes, for several reasons.
First, it was good to know that when something got baggy, I could just dig out something smaller without having to make time for a shopping trip. This is especially true for pants. Some times it seemed like one size would fit okay one day, then the next would be falling off. I'm actually getting a little sad now because I got rid of my smallest clothes a while ago, and am now wearing my smallest pair of jeans.
Second, there is of course money. I know I don't have a lot of money to spend on new clothes, so for me I would much rather spend as little as possible between now and my goal, then to spend it as I go and then not be able to afford to fill up my closet with nice things that fit when I'm done.
Lastly, I admit to being really happy when I'm able to put on something that I haven't been able to wear in a while. It feels like such a big accomplishment to me.
I would think about if you can afford buying new clothes as you go down sizes, and if you like your old clothes. I love a lot of mine, so its a joy to wear them again as I go down, but you might not be as attached to your things.
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