The Best Shoes to Wear with Leggings

A woman wearing nude strappy heels with leggings

Love for leggings has transformed them from strictly workout wear to everyday essentials. If you’re someone who loves leggings but isn’t sure what shoes work best with them, we have the tips to help.

Some shoe styles throw your legs out of proportion when combined with leggings, while others do nothing good for the rest of your figure. So, it’s time to solidify what shoes to wear with leggings with the help of our team!

In this blog, our experts will walk you through how to dress down boutique leggings with sneakers and dress them up with loafers. Check out our favorite shoes to wear with leggings below!

Chunky Sneakers

Look for white, chunky-soled boutique sneakers that can help you look like you’re ready to hit the trails or do a couple of laps at the gym. We love to wear these shoes with leggings as they’re sporty, chic, and comfortable.

Sleek Loafers

Pink mule loafers

If you’ve got split-hem leggings, slide shoes like loafers are a fabulous choice. These shoes are great to wear with leggings because they add some lift, so your leggings hang down along your leg a little bit better. We love a classic black colorway or a deep Bordeaux hue.

Ballet Flats

Next on our list of what shoes to wear with leggings are ballet flats. We prefer leather designs to elevate this look. 

With a slightly pointed toe to elongate your legs and a woven leather that ensures they look expensive, you’ll be comfortable, professional, and stylish in these shoes. When you’re on your feet for hours, ballet flats are the must-have shoes to wear with leggings.


Nude suede sandals

Slippers as streetwear is another trend on the road to wearing more casual clothing out and about. With suede slides that have a bit of embellishment, you’re adding weight to your look, and you don’t seem like you’re wearing PJs to lunch.

We only recommend wearing these shoes with leggings if you plan on keeping your step count low. Most slippers don’t have the arch support to withstand walking around all day long.

Vans-Style Slip-Ons

A classic casual choice that often comes in a wide variety of colors and designs, Vans-style shoes look great with nearly everything—including leggings! We recommend wearing them with no-show socks to keep your look minimalist.

For the ultimate throwback look, opt for the black and white checkered design that adds a little life and spunkiness to plain leggings. They’re also a great choice for a complimentary clashing print.

Lace-Up Boots

A woman wearing leggings with lace-up boots

Whether you’re a fan of the traditional Dr. Martens or prefer a different brand of boot that delivers a punk vibe, this sturdy option is a great choice for winter weather. Protect your feet from rain and snow—and look fashionable while you do it!

Sling-Back Heels

As we move on to slightly more elevated footwear, it’s time to talk about what shoes to wear with leggings that draw the most possible attention to your feet. Funky colored straps with a chunky wooden sole are great for wearing with colorful leggings.

You can also opt for this style of shoe when you want to create a contrast for a black and white outfit.


A woman wearing sporty leggings with Converse shoes

If you don’t love regular sneakers, what other shoe style can keep you looking just as casual? Chucks! Flat, minimalist, and versatile, the high-top style is truly too cool. We love making them an athleisure staple with a casual top and leggings.

The Chelsea Boot

As a sophisticated ankle boot, the Chelsea style is a great shoe to wear with leggings because it’s an iconic design that combines comfort with fashion. Easy to zip up and comfortable enough for a multi-mile walk, they slide right over your leggings to elongate your legs and make you look taller.


A woman wearing heels with denim leggings

You might be thinking that heels and leggings would never work. But that’s just not true, especially when you have leggings in high-end fabrics like leather, suede, or velvet. The perfect shoe to wear with leggings here is a block heel.

This shoe style with a blunt toe will balance your mile-high legs for a modern finish with a contemporary flare. You can opt for an all-leather shoe that has a small heel for support and comfort or go a little higher for a ballet-inspired vibe that makes it look like you’re en pointe.

Over-The-Knee Boots

If you want to look like you have legs for days, the perfect shoe to wear with leggings is the over-the-knee boot. They keep your legs warm, elevate your look, and make you taller with a slightly stacked heel.

Explore suede for your sky-high boots to find a whole range of colors that work with whatever legging hues and sweater prints you have for the perfect winter-weather ensemble.

Cowboy Boots

Woman wearing cowboy boots

Last, but certainly not least, the last shoe to wear with leggings on our list is the cowboy boot. We recommend mid-calf length boots with a low heel for the classic choice that exudes casual country.

These boots have a wide top that will make your calves look slimmer. Even better, the small heel adds a little height but ensures you can keep walking for hours in comfort.

Shop Boutique Footwear at The Willow Tree

Now that you know what shoes to wear with leggings, it’s time to start putting together some looks. Do a little exploring in your closet to see what you already have before trying on our top styles.

If you’re missing a couple of options, browse our boutique shoes today to discover top-quality brand names with trends you don’t want to miss. Share your ensembles with us and show off your best looks!