Leggings may have once been reserved for gym sessions and lazy days, but somewhere along the way, they became one of fashion’s most versatile wardrobe essentials. Blame it on the rise of athleisure in the early 2010s—or the fact that women everywhere realized just how good they feel in a buttery-soft, high-waisted pants—but these bottoms have earned their place as a closet staple. Now, as we wear them to a wider range of occasions, we might start wondering, “What are the best shoesto wear with leggings?”
Their popularity didn’t just happen overnight. As street style started to blur the lines between activewear and everyday fashion, leggings got a serious upgrade. Thicker fabrics, elevated silhouettes and sleek, structured fits gave them a more sophisticated look while still delivering that unmatched comfort. Suddenly, it wasn’t strange to see someone in leggings at a dinner party, especially when paired with a blazer and statement booties. And today? Their staying power is clear—leggings aren’t just for lounging, they’re for living too.
Whether you’re catching a red-eye, running errands or heading to brunch, the right pair of leggings can carry you through your day without missing a beat. They move with you, flatter your shape and, most importantly, they’re comfortable—something we all can appreciate as we age.
Of course, the key to making leggings look intentional (and not like you just rolled out of bed) is all in the styling—particularly your footwear. Need some inspiration? Read on for seven celebrity stylist-approved shoe styles that pair perfectly with leggings, no matter where you’re headed next.
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What Type of Shoes Look Best With Leggings?
The beauty of leggings lies in their versatility. The right shoes can take them anywhere from a laid-back coffee run to a more elevated lunch date, and according to celebrity stylist Brooke Rounick—whose clients include professional athletes and TV stars—the key to making leggings look put-together is choosing shoes that balance their casual nature.
“Chunky or sleek, sneakers add a sporty touch,” she says, while knee-high riding boots “elongate the silhouette and feel classic and refined.”
Whether you’re going for something structured like a loafer, bold like a western boot or chic like a strappy sandal, each shoe brings a different energy to your ensemble. So, instead of reaching for the same pair every time, think about where you’re headed and what kind of look you want to create. That’s the secret to making leggings feel fresh, not frumpy.
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What Shoes Should You Wear With Leggings if You’re Over 50?
Comfort is a non-negotiable—but so is looking put-together. The good news? Leggings can absolutely be stylish at any age, especially with the right footwear in the mix. For women over 50, it’s all about striking the right balance.
“Oversized blazer meets leggings and loafers for a look that reads smart, not stuffy,” says Rounick.
Ballet flats, riding boots and business-casual loafers offer structure without sacrificing comfort, while sporty sneakers and chunky boots keep things grounded and modern. The best part? None of these looks feels overdone. With elevated basics like longline blazers, crisp button-downs or textured knits, your leggings become the base for outfits that are flattering, age-appropriateand endlessly wearable.
How To Wear Shoes and Socks With Leggings
It’s a small detail, but how you style your socks matters. This is especially true when leggings are involved. Certain shoes call for a no-sock zone (sleek sandals and ballet flats), while others look even better when you show off a little bit of sock.
“Let your socks show just a little,” recommends Rounick. “A peek of crew or calf socks over ankle boots adds warmth and intention. It’s the difference between ‘I ran out the door’ and ‘I styled this.’”
For sneakers and chunky boots, try a clean white sock that adds contrast and visual interest. And with loafers, go classic with white or try tonal socks for a monochromatic vibe. The right sock can tie your whole outfit together, so don’t be afraid to let it show.
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The 7 Best Shoes To Wear With Leggings, According to a Celebrity Stylist
1. Sleek sandals
There’s a certain ease that comes with pairing sleek sandals and leggings—it feels laid-back but still pulled together, like you know what you’re doing without making a big deal about it. When temps continue to stay hot, ditching sneakers for a strappy flat sandal gives the look a breezy, more refined twist. It’s perfect for everything from brunch to an art gallery stroll or just running errands with a little extra style.
“The perfect white tee and leggings combo keeps things clean and sculpted—think barely-there effort, maximum impact,” Rounick suggests in terms of what to pair these sandals with.
To keep the outfit feeling fresh, opt for that white t-shirt or a slim tank or soft tee, add a chic bag and let the sandals take the spotlight from there.
2. Sporty sneakers
For days when you’re on the move—whether that means a long travel day, a packed errand run or just clocking steps with a friend around the neighborhood—sporty sneakers and leggings are a match made in comfort-meets-cool heaven.
But this pairing isn’t just about practicality. With the right styling, it’s a whole look. The combo of crisp white sneakers, ankle-grazing leggings and a slightly oversized sweatshirt or bomber layered over a fitted tank is what Rounick calls “a mix of prep and play.”
The key is to lean into contrast, mixing sleek bottoms, structured layers and a colorful sneaker. It’s casual, yes, but when styled right, you could go from a coffee run to an informal meeting without missing a beat.
3. Equestrian boots
There’s a reason the equestrian look keeps trotting back into fashion. It’s timeless and structured, but also gives off a powerful energy. Riding-style boots paired with leggings channel that same aura (no horse required).
The sleek silhouette of a knee-high boot instantly elevates basic black leggings, adding shape and sophistication. When styling, try a “crisp button-down tucked into high-rise leggings, paired with sleek riding boots for a nod to classic equestrian polish,” says Rounick.
To complete the look, try a tailored blazer or a chunky knit draped over your shoulders for that countryside-meets-city aesthetic. The boots do all the heavy lifting—elongating the leg, refining the outfit and making a simple leggings base feel runway-ready.
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4. Business-casual flats
Leggings may be the queen of comfort, but pair them with a refined flat and suddenly you’ve got a look that’s more office-ready than off-duty. The ballet flat renaissance is real, and it’s breathing new life into everyday dressing.
Soft leather, square toes, dainty bows—they bring just enough structure to balance the casualness of leggings without tipping into overdressed territory, says Rounick, who calls this duo “effortless but intentional.”
Try layering a crisp button-down under a slouchy blazer or cropped cardigan, then finish it off with a classic ballet flat or low-heeled pump. It’s a polished alternative to sneakers that works for chill meetings or gallery visits—basically, anywhere you want to feel put together but still comfortable.
5. Chunky boots
Chunky boots and leggings hit differently. They’re bold yet unfussy, making them ideal for days when comfort takes the lead but style still matters. Rounick recommends an “oversized sweater layered over leggings, grounded with chunky UGGs and an oversized bag that looks like it holds your whole life (but in the chicest way possible).” If UGGs are not your style, don’t worry; other types of chunky boots work too.
Want to take it to the next level? Let your socks peek out. It adds a layer of cozy detail that makes the outfit feel thoughtful, not thrown together. Great for travel days, long city walks or just making your morning errands feel a little more elevated.
6. Western style
The western wave shows no signs of slowing, and we’re not mad about it. Fringe is back, denim-on-denim is having a moment and cowboy boots have officially graduated from rodeo staple to an everyday must-have. And yes, they pair surprisingly well with leggings.
A sharp-toe western boot adds just the right amount of edge and personality, transforming your go-to leggings into something a little more edgy and a little more fun. Rounick notes that “western boots add personality to leggings and work especially well with oversized knits or longer coats.”
Throw on a slouchy sweater—or maybe a longline duster or trench— and suddenly you’ve got an outfit that’s cool, comfortable and right on trend.
7. Black loafers
Black loafers are the secret weapon for making leggings look refined without overthinking it. They give off that “I have plans, but I’m not rushing” kind of energy. Paired with a cozy tee, white socks and an oversized shearling or wool coat, it becomes a go-to fall uniform that’s “easy, warm and pulled together,” says Rounick.
“It’s that go-to look that feels low-key but still put-together. Just add loafers and you’re out the door,” she explains.
The white sock peeking out? That’s the styling trick that brings it all together. It nods to British street style but works just as well stateside, whether you’re headed to the boardroom, your favorite coffee shop or even a birthday party.
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Source:
- Brooke Rounick is a celebrity stylist whose clients include professional athletes and TV stars
