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

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The mini skirt is back, folks, and not just in the form of sexy party dresses or tennis skirts. Pleated, A-line, flared and straight silhouettes are all trending right now (and will likely continue in popularity through spring and into summer). Still, these short hemlines can sometimes feel tricky to pull off, especially as an adult, and knowing which shoes will make you look chic and which are best saved for longer frocks can make all the difference. Here are four footware options to try, plus one best saved for styles that show less leg.

These Are the Best Boots to Pair with a Miniskirt (and Not Look Like a Hooch)

woman wearing a mini skirt and flat boots
Edward Berthelot/Getty Images

1. flat Ankle Boots

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)

woman wearing a mini skirt and loafers
Edward Berthelot/Getty Images

2. chunky Loafers

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)

woman wearing a mini skirt and flats
Christian Vierig/Getty Image

3. pointy-toe Flats

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)

woman wearing a mini skirt and tall boots
Edward Berthelot/Getty Images

4. knee-high Boots

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)

Edward Berthelot/Getty Images

5. avoid: High Heels

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.)



Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...