I’ve never considered myself to be a girly girl. In fact, I was pretty tomboyish growing up. I don’t think I started wearing makeup until late into high school. Even at 22, I just stick with foundation and eyeliner. But as I’ve grown older, I’ve tried to change the way I dress.

By trying to dress a little more mature and feminine, I’ve found out that I love heels. Unfortunately, I don’t get many opportunities to wear them. I don’t go out at night very often and I work in retail, so I am stuck on my feet for seven or more hours a day.

I’ve tried my hardest to find cute, comfortable heels but I’ve learned that no matter how great they feel, after only four hours of wearing them (sometimes even less), my feet want to die. Also, I’m pretty sure my feet have swollen at least half a size since I’ve started working.

My feet were wide to begin with, so now it’s even harder to find shoes that fit me well.

Recently, I bought the cutest Steve Madden ankle booties. I mean, seriously, they are so damn hot and I can’t even wear them to work! They felt fine when I tried them on in the store and they were comfortable, so I thought they would work. I don’t know of many places that carry “Wide” sizes other than Payless and DSW. Also, I think I’m just not picking the right kind of heels for my feet. I’ve learned the hard way that just because they are cute, it doesn’t mean they’re going to fit.

When shopping for heels, how can I tell that they will be comfortable to wear? Should I maybe get a half size bigger or get insoles?