outfit: sky high solution

Does anyone else have a heel problem? I'll be the first to admit, I rarely ever wear them. Whereas I used to wear stilettos every day in high school, now I wear 2 inch heels at most, anything higher and I throw some flats in my bag juuust in case. My high school self swore I would't end up this way, but what can I do? I feel more comfortable in flats. Today though, I'm wondering if the problem is not the shoes, but the entire outfit. So, what if we wore heels with a killer casual ensemble? Maybe we can psych ourselves out. Check it:

versus

 

I love this summer look of a loose fitting tee, some ripped up boyfriend jeans, and a knockout pair of pumps. And just in case you're wondering how this get-up works for those of us who are flat-inclined? Gingham checkered D'Orsay flats are the answer (though Birks, grecian sandals, and Toms work, too). Throw on some flowered sunnies to shade your eyes from your own hotness.

Hmm, would you try this?