The 10 Best Shoes to Wear with Leggings, According to a Fashion Editor
Our love for leggings has always been strong. But as this year has tested our relationships with our housemates and the DoorDash delivery people, our feelings for these wonderful, comfy, stretchy bottoms has only intensified. Luckily, being stuck at home has provided endless opportunities to figure out which tops and accessories that make our go-to Lululemons look their best. But when it comes to footwear, we’ve got more than a few stylish ideas. Here, ten shoes to wear with leggings from now until, well, probably the end of 2021.
But first! A reminder of the two cardinal rules of pairing tops with leggings.
Nine times out of ten, wearing leggings with a shirt that hits just above your hips or higher, like a cropped sweater, will throw your proportions out of whack and do nothing good for your figure. (Basically, the only exception is if you’re wearing true workout gear, like a breezy tank or sports bra.) So, stick to longer blouses and tunics and save your ‘90s baby tee for another day.
The second rule is actually the same rule we follow when pairing shoes and dresses or skirts—the shorter the hemline, the shorter your heel should be, and vice versa. While a midi dress looks best with a sizeable heel rather than flats, an oversize knit that hits well below your bum will look better with some block-heel booties than flat loafers.
1. Contrasting Ankle Boots
The key to pulling off skin-tight black leggings and snakeskin ankle boots—whether they’re deep brown or bright white—is to find just the right shaft height and width. This is not the time for ankle-hugging sock booties, so opt for structured leather instead, that leaves a bit of room between the boot and your leg. As for height? Look for something that hits about two inches above your ankle bone.
2. Black Boots
This is probably the most foolproof duo on this list. Almost any combination of black leggings and black boots will work well together. Yup, that rings true whether you opt for leather ankle boots, suede thigh-highs or even rubber wellies. That said, faux-leather leggings or spandex with some shine can be trickier to style than matte pairs because mismatched shine can end up looking cheap. Err on the side of caution and stick with matte bottoms…until you have time to truly nail down the right duo.
3. Leather Wellies
Leggings are great for rainy days, and not just because they tuck easily into tall boots and thick socks. Many of the sporty options out there are made to wick away moisture and dry quickly. For true protection from the elements, opt for knee-high boots instead of short Chelsea styles and balance out a chunky sole with a more streamlined top, like a crew-neck knit or button-down shirt.
4. Over-the-Knee Boots
On their own, both thigh-high boots and leggings can make your gams look a miles long. So, combining them into one look only serves to strengthen that supermodel effect. For this pairing, we prefer to keep colors close to one another or matching, i.e., black with black, dark brown or dark gray. Or, if you do decide to try a contrasting boot, consider wearing a top that coordinates with the color of your leggings to lengthen your top half as well.
5. Kitten Heels
Heels and super-tight pants are a tricky combination—both serve to elongate and slim the look of your legs and can easily turn your silhouette into an apple stuck on two popsicle sticks. But one version we’ve found to work time and time again are leggings cropped right at the ankle worn with pointy-toe kitten heels. That slightly abbreviated cut mimics one of the most flattering pants lengths and the flash of skin provides just enough of a break between your bottoms and your shoe.
6. Minimalist Sneakers
Sure, you could try balancing a pair of chunky dad sneakers with a thick cable knit sweater, but we prefer the streamlined look of minimalist kicks with leggings, instead. These simple, no-fuss, low-top styles work with just about any length or style (yes, including leather and faux leather), so long as the hem hits somewhere between one and three inches above the top of your shoe.
7. Contrast Combat Boots
These chunky ‘90s-inspired kicks work best when the shaft hits max three inches above your ankle bone. Similar to leather ankle boots, you want there to be a clear delineation between your calf and the shoe, rather than one long continuous line. This helps your legs look nice and lean in comparison to the lug sole and heavy hardware on your Dr. Martens. Even better if you choose a bold color like white or cherry red.
8. Hiking Boots
Compared to combat styles, hiking boots tend to have a shorter shaft and more rustic detailing but are often just as clunky with heavy lug soles. Steer into the cozy vibes that naturally accompany these outdoorsy shoes with some standout socks peeking over the top. Basically, you want to fake a taller boot with the help of a thick knit sock, but again, try not to go too high above the ankle bone (three inches or less should work well).
Ballet flats can also look great with leggings, but the key is finding a pair of shoes that aren’t cut too low. Loafers and other styles that don’t run the risk of exposing toe cleavage work in much the same way as low-top sneakers; they give an Audrey Hepburn vibe we can’t get enough of and go with just about any pair of leggings in your arsenal. This is one instance where you want to steer clear of "boring" or "basic" styles; anything with a bow, buckle or bold pattern is a better choice. And remember to choose a slightly longer top to balance these minimalist flats.
10. Square-Toe Shoes
We already mentioned that leg lengthening pumps aren’t always a great partner for slimming leggings, but there are some heels that still work well, like block heel, square-toe styles. You should still keep the heel to three inches or less, or you can even try flats, but the blunt toe helps to balance out your mile-long stems for a more proportional (and modern) finished look.