How to Wear Leggings for Nearly Any Occasion, According to a Style Expert

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The rise of athleisiure has made leggings a fixture of our wardrobes for many years now. And with comfortable clothing still a top priority for many shoppers, the silhouette remains a go-to choice for work, play and everything in between (even countless celebrities like Kendall Jenner, Gigi Hadid and Karlie Kloss still can’t get enough of their leggings).

Yes, there are plenty of technical workout leggings that prioritize performance, but a growing number of clothing and intimates brands like Spanx, Wolford and Nadaam are also offering styles in more luxurious textures including cashmere, faux leather and velvet that are perfect for evening events or days spent in-office. Today’s leggings also come in a range of lengths and silhouettes, depending on the activity you plan to use them for or your aesthetic preference.

Different leggings styles

  • Full-length: With an ankle-grazing hem, these are the most versatile types of leggings that can be worn with nearly any choice of footwear. These are also the best styles to wear with crew socks to avoid any weird gaps.
  • Capri: These ’90s-inspired silhouettes typically hit just below the knee and are making a comeback.
  • 7/8: A good middle ground between the capri and full-length legging, these hit just above the ankle. They’re especially popular for shorter women and as styles for working out to give the legs a bit more breathing room (especially when paired with no-show socks).
  • Flared styles: ’70s-esque flares are having a huge moment across all different pant categories, including leggings. These options were also probably what you remember when leggings first became popular as athleisure styles in the early aughts.
  • Split-hem leggings: An Instagram and celebrity-favorite choice, this contemporary trend features a subtle slit down the front that’s perfect for showing off your favorite shoes.
  • Stirrup leggings: Now popular once again, the ’80s-inspired stirrup legging has an elastic stirrup that’s meant to be worn over the shoe, fitting over the middle of the outsole, for a detailed finish.

Even after finding the right pair for your needs, however, the pieces you style it with are just as important to ensure your look is both occasion-appropriate and effortlessly chic. To help de-mystify this often puzzling equation, we consulted FN’s Style Director Shannon Adducci to discover exactly how to wear leggings the modern way, for nearly every occasion.

Discover her top tips ahead.

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Elevate your leggings with heels.

“The legging may seem like a sport-centric item, but fashion’s recent obsession with bodywear says otherwise,” says Adducci. “Think curve-hugging full-length catsuits and high-heeled sandals a là Cardi B or the classic leggings-and-stilettos pairing that has traversed through the ‘80s to the aughts to now.”

A pair of vibrant leggings is the perfect companion to some glitzy heels done in complementary hues, but a black option can also feel evening-ready when done in sleek fabrics and styled with stilettos.

Other popular leggings-and-heel combos include stirrup-style leggings and pointed-toe pumps for an of-the-moment layered look.

leggings and heels
CREDIT: Courtesy of Joshua Scott

In photo: Calzedonia Active Leggings, Jimmy Choo Saeda Satin Crystal Ankle-Strap Pumps

Throw a dress on top with platform boots or sandals.

The controversial 2000s-era trend of wearing dresses over pants is back, and with the right styling, Adducci says it can apply to leggings, too. The trick, she says, is to keep colors neutral and completely matching — or go for a full-on statement with double the color. Platform boots or summer sandals are the best pairings, as they’ll add some polish to the look to prevent it from venturing into kitschy territory.

Style rolled-up leggings and 2000s-inspired accessories.

If the current Y2K aesthetic is really your speed, consider rolling up a pair of full-length leggings and pairing them with kitten heels and a mini bag. “Rolling up the legging to show more ankle is a direct reference to the decade’s obsession with the capri pant,” Adducci suggests. (Of course, you can also opt for a capri option, but the former method is perfect for those who already own a classic pair of leggings and want to double dip with the style.)

leggings and kitten heels
CREDIT: Courtesy of Joshua Scott

In photo: Lemon fleece-lined leggings, By Far Freya knotted leather mules, By Far Amber lime green semi patent leather bag, Jennifer Fisher chain-link cuff and brass ring

Stick to all-black for the office.

Leggings can work for more casual office environments, but black pairs are always the most office-appropriate. To make them better blend in with the rest of your outfit and elevate the look, add on a coordinating black blazer, coat or sweater. Ideally, Adducci mentions these pieces should cover the waistband and the hip and butt area for modesty. And, “make sure your black leggings are truly opaque,” she says. “Ask someone close to you to assess for you in bright lighting if you’re unsure.” Black stirrup silhouettes are also a great option for the office.

Use black patterns and accents to create depth.

When wearing patterned leggings, choose sneakers or socks with subtle black accents to balance out the look, Adducci says. Even better if your leggings have a touch of black in them to fully tie the look together.

leggings and sneakers
CREDIT: Courtesy of Joshua Scott

In photo: P.E Nation Retrograde short in print, Louis Vuitton Archlight sneakers, Alo Yoga Women’s Throwback socks, Maria La Rosa Mesh Socks

Poke your stilettos through footed leggings for an advanced look.

Looking to get a little extra creative with your leggings outfit? “Mirror the look of Balenciaga’s cult Knife boots and poke a pair of stiletto pumps through the back of close-footed leggings or stockings for an unexpected and elongating look,” Adducci says. “Just be sure that you’re ok with keeping the hole in the legwear — this is a permanent styling technique!”

Add on a cool sock.

Instead of reaching for classic no-show or crew socks, spice up sporty legging-and-sneaker combos with fashion socks featuring mesh or lace accents. This creates an eye-catching juxtaposition and interesting detail at the ankle.

leggings and nike sneakers
CREDIT: Courtesy of Joshua Scott

In photo: Tory Burch high-rise Weightless chevron leggings, Nike Women’s Air Zoom SuperRep 2 training shoes, Maria La Rosa mesh socks

Coordinate your leggings to your sneakers for a low-key yet high-impact look

While a neutral, monochrome look is always on point, consider pairing colorful leggings with coordinating sneakers on days when you want to switch things up. “It’s a directional approach to an off-duty outfit, but the attention to coordinating color and pattern will go a long way when it comes to ramping up an everyday look,” Adducci notes. Keep your top neutral and solid-colored (in black, white or natural), she suggests. A cozy hoodie, light jacket or chunky sweater will give your ‘fit additional street cred.

colorblock leggings and sneakers
CREDIT: Courtesy of Joshua Scott

In photo: Split59 Janis High Waist Techflex 7/8 leggings, Chloé Nama sneakers

Pair colorful leggings with white sneakers and crew socks for a retro vibe

Take a page from Princess Di’s style book and rock colorful leggings with white crew socks and multi-media sneakers for instant ’90s vibes. Adducci advises matching one accent color from the sneaker to the legging for the most cohesive look.

colorful leggings and sneakers
CREDIT: Courtesy of Joshua Scott

In photo: Nike Dri-Fit One Luxe buckle leggings,Dolce & Gabbana Airmaster sneakers, Jennifer Fisher small link chain anklet

Wear leather leggings with contrasting textures and rugged footwear.

Perfect for date night or slightly dressier occasions, leather leggings look stunning when paired with luxe, soft textures that create a nice contrasting effect. Try a cable-knit jumper or long cashmere duster to nail rich-mom vibes, and add on a chunky platform or combat boot for an of-the-moment twist.

Wear flared or split-hem leggings with combat boots or statement sneakers.

“Flare and split-seam bootcut silhouettes are also on the rise,” Adducci says, adding that these retro-style leggings look even more fashion-forward with a pair of chunky combat boots or statement sneakers. Consider choosing a split-hem version for an even more modern take.

split hem leggings
CREDIT: Courtesy of Joshua Scott

In photo: Alo Yoga Airbrush Flutter Leggings, Jimmy Choo neoprene Cosmos shoes

Below, shop other great legging and shoe options this season.

Year of Ours Football Ribbed Lace-Up Leggings
CREDIT: Courtesy of Backcountry

Port De Bras Lisbon Leggings
CREDIT: Courtesy of Saks

Fabletics Define High-Waisted Crop
CREDIT: Courtesy of Fabletics

New balance 327
CREDIT: Courtesy of New Balance

Veja Venturi Sneakers
CREDIT: Courtesy of Bandier

Jeffrey Campbell Mood Platform Sandals

Photographer: Joshua Scott
Style Director: Shannon Adducci
Editorial Assistant: Tara Larson
Parts model: Farrah Sabado at Parts Models

Meet the author

Sam Peters is the senior style commerce editor at Fairchild Media Group (FMG), where she always up to date on the latest trend and tests out various apparel styles to find the best in each category. She’s worn a range of top legging silhouettes for women and has been known to style some pairs outside the gym and dance studio, both of which she frequents.

Meet the expert

Shannon Adducci oversees fashion coverage for FN, outlining the top trends and moments of the season. She also cultivates relationships with designers, directs FN’s cover shoots and travels to major fashion weeks and events globally.

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