I have had soooo many female clients email me in distress about what they should wear to whatever session we have coming up together. My first and most emphasized advice? Wear what makes you feel confident & comfortable!
The key to a successful portrait session is to be confident with what you're wearing. Even I, a mere mortal, have photos of myself that I do not share (insert sad face). I don't share them because I hate the memory, they just do not see the light of day solely because I was miserable in that outfit. Uncomfortable, itchy, the dreaded all black phase, or it was just downright unflattering! We've all been to the Land of Regrettable Wardrobe Choices. I think it's about two islands South of the Land of Misfit Toys ;) Trust me, friend. You're not alone.
My second piece of go-to advice for all of my feminine clients? Wear a dress and make it maxi! There is just something about dresses that photograph SO FRICKIN' WELL. Also, then you can get away without shaving your legs ;) Shorter dresses can bring it pretty movement, too! The Midwest weather can get a little unpredictable at times, so if the wind decides to catch the skirt and make it twirl or not is totally fine with me! Flowing skirts give so much body and movement to images. You'd be surprised to see how much of a difference they can make!