The "most money on single piece of clothing" is, for me, a little bit of a misnomer; it's really "I've spent more than $500 on specialized sports equipment that I then wear," and when the sport is skiing, everything is mind-blowingly expensive and parts of it (boots, skis, gloves) are really not worth skimping on. Spending $50 for a pair of socks isn't out of the question. (But while you can spend $193 for a nice long underwear top, that's one thing that isn't worth it.) And then I started grad school and haven't skied since. But if I lived nearer a good mountain, I'd spend money so fast my head would spin.