The Best Shoes to Pair with Every Type of Pant
M.M. stylists weigh in on the best heels, flats, and boots to wear with wide-leg, skinny, cropped, and loungewear pants.
What do Shakira, Kamala Harris, Zoe Kravitz, and Melissa McCarthy have in common? Other than being on the list of people I’d most want to do karaoke with, they’re all under 5’4” tall, which means every single one of these intelligent, talented, and shorter women has likely fallen in love with a great pair of pants, only to wonder what kind of shoes she should wear with them.
To be sure, the often confusing mathematics of pairing pants and shoes isn’t just the provenance of petite women. As M.M. stylists often report, women of all heights, shapes, and sizes struggle to find the right pair of culottes to wear with a new pair of heels, and voice concern that they’ll look sloppy in sneakers and wide-legged jeans. And joggers? They come with their own set of questions.
But here’s the thing: whether you’re 5’2” like Shakira or 5’10” like Taylor Swift, finding the best shoes to pair with every type of pant comes down to three things: hem length, comfort, and personal style.
Below, with the help of M.M. stylists Joanna, Chris, and Kate, we break down which shoes to wear with some of your favorite pants.
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The Best Shoes to Wear with Straight, Full-Length Pants
Straight-legged, full-length pants are a wardrobe essential for a reason—they create a solid base for an outfit, elongate the lower half of your body, and can be styled in infinite ways. You could show a little toe by pairing the Foster pants with the Ella sandal, or show a little ankle in the Grace loafers and the Hockley jeans. Remember, hem length is important here, because as Chris points out, “you don’t want your pants to be too long if you’re wearing flats.” Thank goodness the Hockleys have adjustable hems. If you really want to step things up, Chris recommends pairing the glamorous pointed-toe Lana boots with a pair of FRAME jeans.
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The Best Shoes to Wear with Wide-Leg Pants
Joanna is only 5’2”, but she doesn’t let that stop her from wearing her favorite wide-leg pants. For additional height and polish, she likes to go with a pointed toe, like the Ginger pumps with the Anderson pants, or the Lana boots with the Milo jeans. “But,” as Joanna points out, “Even if you’re petite, you definitely can’t go wrong with a flat shoe and a wide-leg pant.” Again, you want to be mindful of hem length (you definitely don’t want your pants dragging on the ground), but you shouldn’t be afraid of wearing wide pants with flats—especially a great pair of sneakers, like Koios.
The Best Shoes to Wear with Cropped Pants
Can petite women wear cropped pants? Our answer is a resounding yes. In fact, most of my pants are cropped. The trick to styling shoes with cropped pants and not looking like an extra in Newsies is embracing the bare ankle and going with an elongating, feminine shape. Personally, I find the Ella sandals to be a glamorous combination with the Zhou culottes. For a great Power Casual look, the Rowan flats are an elegant option with the Mejia pants, as are the Lana boots with a pair of cropped jeans. What about tall women? “A friendly reminder for tall people like me (I’m 5’10”),” says Kate. “It’s okay to show some skin! Your boot and hemline don’t have to meet.”
The Best Shoes to Wear with Skinny Pants
Skinny pants have a similar playbook as straight-leg pants, but these days, many skinny pants are also cropped. This style elongates legs, shows off the ankle, and is incredibly versatile—and when it comes to shoes, you really can’t go wrong. Want to show up to a date looking fancy and sleek? Go with the Ella sandals and the Curie pants. Need to run errands while looking like an off-duty Catwoman? You’re going to want the Koio sneakers and the vegan leather Harrington leggings. And for a lengthening, stretchy ensemble? The Zelda boots and the jardigan knit Finley stretch pant are a must.
The Best Shoes to Wear with Leggings and Joggers
Since spring of 2020, leggings and joggers have become some of the most-worn pieces in our wardrobe. And while they’re perfect for lounging around on the weekend or taking Zoom calls from bed, we’re on a mission to breathe some new life into them. “We’re in a time where comfort has become a big priority for many,” says Chris. “I also think there are great ways to wear flats or heels to dress them up a bit.” So yes, go ahead and pair your joggers with sneakers, but maybe also try a pair of Grace loafers. Or, what about a leggy moment in a pair of Stellas and the Ella sandals? The important thing to keep in mind is that your joggers or leggings should be as crisp as your shoes. For example, next time you’re just grabbing drinks and apps at the bar, you can definitely dress up your joggers with the Lana boots—just make sure those joggers are a little luxurious, like our cashmere Keely joggers.