Shoes.

I'm rough on shoes, very rough.  My wife and I are at the gym and she sees my shoes and tells me I need to buy some more.  I don't really think I need more shoes but then I can relegate these to "lawn" shoes and get some better ones for bike riding or in the gym.  There's an outlet mall near us so I bundle up a minion and we go.

Three stores that sell shoes.  You know what size I wear?  10.5 triple wide.  Just give me the damn box and paint it black.  At one store it only had dress shoes, something to keep in mind but not what I'm looking for now.  One didn't have any wide or extra wide widths; they did but the guy that worked there said to not get them if I plan on using them instead of just looking cool.  The third store had wide shoes but they were not something I would wear.  I dress rather...somber, professional, basic.  Those are all good descriptions of my style, except for ties though.

I have a friend that always has problems getting cute bras that fit her.  She is some bigger size like 32DD or 34GG or some big combination of letters and numbers and I remember her complaining (on more than one occasion) about the lack of bra selection in her size.  I have the same problem in shoes, if I find shoes that fit then they look like a crackhead on acid painted them.