I love demure and girly dresses like this long-sleeved dress from Madewell with a dropped waist, mock turtleneck, and feminine smocking details at the neck and wrists. But when the occasion (or my mood) calls for something less sweet, I like to toughen up a pretty-girl dress with socks and ankle boots.

For this look, I took a page out of the 90’s grunge-era playbook (an era that’s making a comeback, by the way), and I love how it turned out.

The hemline is just short enough to accommodate a slightly taller boot like these faves of mine from Rag and Bone, but short enough to be fun and flirty for an evening out with friends or date night with my husband. I added a pair of statement earrings for a dash of evening glam, too, which elevated the outfit a bit. And while I like getting a break from all the black, this look will work with a pair of black, opaque tights, too, when the months get cooler.

Keep scrolling to shop my pretty-yet-tough girl look and similar dress styles below. (Both the dress and the boots are on sale.)

Thanks for reading,