The Best Shoes to Wear with Short Skirts and Dresses (& One Pair to Avoid)

It doesn’t matter much whether you opt for Chelsea boots, Western styles or trendy lace-up Dr. Martens—a flat shoe that hits right above your ankle still lets you show off lots of leg without throwing your proportions out of whack. It also helps to ground such a foxy skirt.

Shop similar styles: Reformation coat ($328); Lucky Brand T-shirt ($15); Missguided skirt ($32); Dr. Martens boots ($150)

Whether you go lug-sole or traditional, we recommend pairing this preppy shoe with contrasting skirts and dresses, like a ‘60s shift or sweaterdress, rather than anything pleated or plaid, which could end up looking like a schoolgirl costume.

Shop similar styles: Rachel Comey dress ($415); Loeffler Randall bag ($295); Sam Edelman shoes ($150)

If flippy hems, pleats and plaid are your bread and butter, however, a pointy-toe flat is just the thing to balance them out. Rounded toes can look a little juvenile when paired with a mini, but a sleek pointed toe works to elongate your legs and lend a professional, grown-up vibe to your ensemble. Of course, they’ll also work with straight-cut skirts and structured A-lines too.

Shop similar styles: Alex Mill shirt ($98); Susana Monaco skirt ($108); Strathberry bag ($415); Vionic flats ($120)

The key is to choose a boot with a flat sole or low block heel (we’re talking two inches tops) and enough structure so that it neither slouches down nor clings to your calves. We particularly love the juxtaposition between tough riding boot styles (think equestrian or moto) and a fun print like plaid or florals, though you can always wear them with neutral hues as well.

Shop similar styles: Ann Taylor sweater ($95) and shell ($65); ASOS skirt ($36); Naturalizer boots ($240)

Repeat after us: The shorter the hemline, the lower the heel. A miniskirt worn with sky-high stilettos will likely throw off your proportions and make your torso look squashed, or worse, appear a little tacky. Save your stacked booties or stiletto pumps for midi and maxi dresses instead. (And don’t worry, your legs will still look amazing in flats.)