This is a horrible day to arrive at, but I'm going to have to buy some flat shoes that are not sneakers. After so many years of wearing 4 inch+ heels for 10 hours or so a day, my feet now prefer to walk to and from work in flats (HORRORS, how embarrassing). Even more embarrassing however is the fact that these flat shoes have been over the last year or so, Converse sneakers (yup, the ones preferred by 20 something hipsters in skinny jeans).

Granted, some days I do wear skinny jeans; but on other days I have to admit they look quite ridiculous with what I'm wearing. I was trying to convince myself that it was okay, with the anonymity of the city, and since it was only back and forth to work.... But after merciless commentary at my office I realize I should get something flat and comfortable and slightly more attractive.
An obvious choice is the ubiquitous Tory Burch flat.

I am fairly certain that almost every girl on the Upper East Side has some variation of the Reva flat. Personally, I would never get them with garish gold insignia on the toe. The black version above is less obnoxious. These are $195 at Bergdorf. I think that's a bit excessive considering I am trying to replace a $42 sneaker and these are meant to be primarily utilitarian. I would NEVER wear them for fashion, I just don't believe in flats, plain and simple.
The only other shoe I can think of was this ballet flat with a Chanel-esque black leather camellia flower on the toe that I saw at the Shoe Box, they were an obscure Italian brand called Prego - - and were $300! Crazy. At least those would be more original...

Funny you should mention these Converse sneakers. I was recently subjecting myself and my better half to a viewing of the recent teenie film phenomenon "Twilight", and I happened to mention to him that nothing depreciates an outfit more than a pair of those sneakers...no matter what age you are. There is something so indolent about them. I am glad that you are beginning to see the light and taking the time to scour the shoe world for an acceptable and more lively alternative. I do so enjoy reading your blog and find myself agreeing with nearly everything you have to say about, well, everything.
Keep up the great work!