* When I was younger and dumber I waltzed into Neiman Marcus and picked up a pair of Christian Louboutin heels. ~$400? I think I told myself they were a BIFL purchase that I would be able to use for work stuff. Well, they are just really painful stiletto high heels, same as it ever was. Also, did you know that pregnancy can cause your shoe size to change? After I had my first kid I went from a 6 to a 6.5/7 and the fancies were unwearable. Also, I became a SAHM. So I sold them on eBay. I'm really more of a Keds/Vans person anyway.
* I have a couple of All-Clad pans that I like just fine (one was steeply discounted when Linens 'N' Things when out of business, one I paid full retail), but I've found that I don't really need it when I have (a) the inherited Revereware I got from my grandma and supplemented with $5 thrift finds and (b) vintage cast-iron skillets and a Dutch oven from estate sales. I have lost any ambition to have a suite of All-Clad cookware. Ditto Le Creuset, at least until pots can become like the characters in Beauty and the Beast and actually do all the work for me.
* Expensive private universities for undergrad. I have been to the mountaintop and trust me, your local state school is a better value. If you have infinity fuck-you money or a specialty field of study, maybe worth it, but for general liberal or technical education, just go to State U and then if you want to specialize, go to Fancy U with grants and government subsidies for grad school. From 18-21, you can network just as damn well locally as you can at Yale, etc.