So I came to the conclusion that I would like to start wearing heels casually.

In the process of learning to dress better, I've discovered a previously untapped obsession with shoes in general and heels in particular. Which is great, but actually wearing heels in my everyday life has been attracting a lot of comments along the lines of "what are you so dressed up for?" and "you look nice" (subtext: "what are you so dressed up for?")

A couple examples of what I mean: ankle boots with a stacked heel, plain pumps, t-strap pumps, and finally these bootie-ish things. The Nine West ones are exact, the other are approximations of what I have. I tend to wear them with jeans and a sweater or casual blouse, or with tights and a skirt or dress.

I thought the result was appropriate for casual wear (shopping, lunch with friends, movies, general non-work daytime activities). Have I goofed? Or do I just have non-fashion forward acquaintances and need to suck it up?

I do know that shiny, strappy, and super high heels are no-nos for daytime; but I had to learn there any more guidelines like that?

That said, some things I do to help tone it down.

A pointy-toed stiletto shoe is really not daytime-casual appropriate, even if you are rocking "smart casual" they are liable to make you look too dressed up, especially in a dark color. The vince camuto and mod cloth shoes fall into this category. Save those for evenings, where you can pair them with nice jeans or sleek skirts for a nice evening look that is still bar or concert appropriate. Just tone down the rest of your outfit with a shoe like that.

A good, casual day-time heel is going to be 2-3 1/2 inches with a thicker heel (preferably stacked or wedge) and almond-shaped toe. The ankle boots from target are a good example and are absolutely casual, if your friends think you are dressed up wearing those that is their issue!

Compare clarks wessex wyvern with the vince camuto pumps you posted. The clarks have an almond shaped toe instead of pointed, and the heel is thicker overall and also has a much more gradual taper to the bottom, and the sides of the shoe come up slightly higher. This makes it a much more casual shoe.

In addition, it comes in lighter colors which make it even more casual, the "mushroom" being the most casual of the options.

Mary-janes are also a very casual style of heel. Some people don't like them, but personally I have a pair of red suede mary janes similar to these and get loads of compliments in casual situations. Wedge heels have a similar casual overtone.