Okay, so I'm just starting to move out of my mom-iform of jeans and sneakers, and one place I'm in need of serious help is footwear. Where to begin??

I have plenty of Converse, a good pair of brown Frye boots, a beloved pair of lace-up Docs (also brown), and...that's mostly it.

I'd like to add something fun that supports my general tomboy vibe, that would work with all the grey/navy I wear during the winter, and that is comfortable for playgrounds and story times. I'm a stay-at-home mom, so work-appropriateness isn't an issue. Oh, and I have wide calves. Yay.

I just tried the Seychelles Lucky Penny in pewter because I wanted something more interesting, but when it arrived I found it a little too...cowboy-esque in shape. I live in Oklahoma, so anything that is vaguely cowboy-boot-like reads as straight-up cowboy. And as I already own a pair of cowboy boots, I don't need anything more in that vibe. I think I'd get a lot of use out of an oxford, but I'm slightly overwhelmed by all the variations.

What might you all recommend? What would make a good foundation shoe for this casual, menswear-loving mom?