I am a flat connoisseur — really, I am. My shoe collection is about two thirds flats one third heels and a few pairs of boots too! My boyfriend is only one and a half inches taller than me (that half inch is important!) and I feel awkward walking next to him in a pair of four-inchers so mostly I just gravitate towards a pair of flats and plus, they're more comfortable for long days at work!
I am not one to choose a pair of typical shoes. I do not own a pair of nude flats or plain black, it needs some character since you're compromising on the height. Choose a pair with a little versatility, like my very favorite pair of flats ever, the Frye Regina Studded flats in brown. They are neutral and can be an edgy touch to a feminine outfit.
Even though a pair of shoes only goes with one or two outfits in your closet, if you love them — buy them! It will inspire new ideas or your next shopping trip you'll revolve outfits around the new shoes. Like the Alice and Olivia heart flats, wear them with a plain grey sweater (save or splurge) or a solid-color lace dress (here) — just a little whimsical touch!