And I agree that it’s worth spending some extra money on something (like shoes) that are supposed to be comfortable and last a long time. I just have horrible, horrible comparative shopping urges, making it difficult for me to make any decisions… It’s the same reason I ultimately have issues spending lots of money on clothing.

I’m working on it, though. Even better when my mom pays for the shoes! (And thanks for the tip on buying a size up. Unfortunately, I’m a womens 10; 10s and 11s aren’t impossible to find, but they’re on the upper end of what stores usually have. The plus size is they’re often the sizes that end up on sale.)

Expensive shoes are usually worth it. They’re almost always made of higher quality materials that breathe better and just feel better all around. The most expensive pair of shoes I ever bought cost 240 on sale + with my employee discount at Nordstrom, where I used to work. It was a pair of Cole Haan boots made with Nike Air technology. They have pretty high heels, but they feel fabulous. Indulge me and allow me to share a pic:

http://g.nordstromimage.com/imagegallery/store/product/MediumLarge/4/_5918644.jpg

Yes. THOSE are comfortable. Really.

I rarely buy shoes at TJ Maxx or something because I end up getting ones that are cute but end up killing my feet. I’d say the way to go is to have a certain shoe budget and to spend it on very few pairs of well-researched, expensive shoes once they’ve gone on sale. Also, it’s not always possible, but trying to buy a size up and then stuff the shoes with every manner of padding on all inside parts is something else I do. My mom does it too, and she’s a flight attendant who is on her feet 14 hours a day while working, so if she says it works, it definitely works.