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I spend the most on shoes, because they are so hard to find for proper fit, and support. And, because I wear a size 101/2, they really can be hard to find. I haven't had to do this recently, but I have paid over $200 for a pair of shoes. I don't think I have ever paid that much for a single garment though.
When I was working, I did shop for nicer clothes, and I have paid well over $200 for several garments bought at one time.
Now that I think about it, I might have paid around $200 for a leather jacket I still wear. But, honestly, I haven't gotten the money I spent out of it. I don't wear it often.