What To Wear With Leggings: Live, Lunge And Lounge In These Styles

If you’re at all like us, you’ve been living in leggings lately. What’s not to love about that? The style and comfort once designated an athleisure and loungewear essential, can now take us anywhere. This weekend warrior and style staple is also our go-to from dawn to dusk. They do it all. Leggings are one of the most versatile pieces in your closet. We’ve got a mountain of this four-season favorite just waiting to be styled in a multitude of ways. Join us as we dive deep into all things to consider when wondering what to wear with leggings

What To Wear With Black Leggings

Do you swear your piled-high collection of black leggings has no two that are the same? Don’t worry—we believe you. From the pair you jump into for your morning workout to the ones you love to dress up for date night. You’re not alone if you have a few (or more) pairs of black leggings you cherish. What to wear with black leggings, you ask? The options are literally endless. Ditch the notion that black leggings are a trend. The truth is they’re here to stay, so let your imagination run wild with all the different ways you can wear your leggings. 

Black leggings have enjoyed a prime spot in our closets for decades. Audrey Hepburn’s monochromatic look anchored with black leggings in Funny Face introduced us to this boho beatnik style. For her character’s edgy transformation, Olivia Newton-John as Sandy in Grease was famously sewn into her black leggings. Modern-day icons Beyonce and Jennifer Lopez are known to flaunt their figures in black skin-tight leggings. They paved the way for self-love and provide us with inspiration for what to wear with leggings—day or night.

Athleisure Style Basics for Black Leggings 

American fashion designers artfully blend workwear, leisurewear and performance wear for our busy lives. The result is the ever-growing athleisure trend where you can wear one look for all occasions. From sports to school to work to casual events of all kinds. You can’t beat pairing your black leggings with a hoodie and sneakers for a classic athleisure look. 

Looking to uplevel your athleisure game when figuring out how to style leggings? Try a cropped ribbed tank with black leggings for a morning yoga session. Savor your savasana, but consider this next tip when it’s time to roll up the mat. Toss on a denim jacket and add a pop of print and color with a headband. Opt for finishing touches like a crossbody bag with a ribbon strap when taking your look from the studio to the street. Voilà—you’re instantly ready for a coffee date and running errands in style. See? Athleisure does it all and goes leaps and bounds beyond the couch. 

Dress Up your Black Leggings 

Are you ready to get dressed up again, but not quite ready to give up comfort? You don’t have to. When deciding how to style leggings, think of them as the building blocks for a dazzling look for an evening affair. To start, select a pair of black, dressy leggings (yes, that’s a thing). Fabrics like leather, velvet and Ponte are luxurious options that are just begging to be jazzed up. 

Style your black leggings with ornate strappy heels and an elegant wrap-blouse with a flattering v-neckline that frames your face. Now, all you need are accessories. Opt for lovely links with an on-trend chain necklace to raise the style standard. For a chain reaction, round out your accessories with a quilted handbag with a chain strap. This French-inspired classic will hold all of your essentials in high style and add instant glam to your night-out ensemble.

What To Wear With Grey Leggings

Wanting to break free from an all-black legging collection? When thinking about how to style leggings, shades of grey offer a subtle alternative without going too bold. From soft dove grey to deep charcoal, there’s an array of hues to choose from. Light grey leggings work wonders for casual outings and workouts, while dark greys can add a moody aesthetic. When wondering what to wear with grey leggings, no color is off-limits. Grey is a sleek neutral that allows your favorite colors to take the spotlight.

Style Grey Leggings with a Pop of Color

We can’t resist pairing grey leggings with splashes of color, from autumn jewel-tones to soft spring pastels. Wondering how to style leggings for your next date night at home? Slip into comfy grey heathered leggings and an oversized crewneck sweater for your Saturday siesta. Ready to venture out? Complete this timeless outfit with a string of pearls and brown riding boots. Knee-high boots will easily go over your leggings to create an effortlessly chic vibe. 

Active and Performance Wear: Grey Leggings for the Win

Minimalism and comfort combined with modern performance properties are quintessential elements that make your favorite grey legging a workout staple. When researching how to wear leggings with performance properties, look for these key features. Four-way stretch, quick-dry and moisture-wicking properties will support you through your HIIT workout to grocery pick-up with ease. Are you looking to build a more sustainable wardrobe? Opt for a pair of leggings from brands like Girlfriend Collective or Threads 4 Thought. Both brands use environmentally friendly materials, like organic or recycled fabrics, with the performance properties you’ll love. 

Pondering what to wear with grey leggings on an active day? Add a pop of print with a floral sports bra for a feminine twist to your performance wear look. A zip-up hoodie or jacket is an ideal light layer for your post-workout needs. Look for legging details like cutouts or a decorative racing stripe to step up your look. Oh, and don’t forget a side pocket to hold your necessities. Having your phone hands-free allows you to rock out to mood-boosting jams or catch up on your favorite podcast.


What To Wear With Camo Leggings

If you haven’t jumped on the camo trend, there’s still time to enlist. Before you decide what to wear with camo leggings, you’ve got to pick a color. Choose from subtle greens and greys to magnificent pinks and blues. Ready to be a trendsetter? Head straight for a black-on-black pair of camo leggings. This print will add a touch of glam to your casual outfit. Style them with a tee in a cropped length and a pair of embellished sneakers for sparkle and shine. 

Camo is a fun print that can disguise itself as a versatile neutral. Up your style game and experiment with pattern mixing for your camo print leggings. How do you style leggings for a preppy twist? You can’t go wrong with a striped knit top. This classic combination gives the edgy camo pattern a timeless feel. The finishing touches for a rainy day? Hunter green wellies and a bright yellow rain jacket are style winners. Extra style points for gold hoops, bangle bracelets and a chic waterproof tote to keep your necessities dry.

What To Wear With Leather Leggings

Leather leggings are on-trend and every fashionista’s go-to. Edgy and striking, we’ve got a few simple style hacks for what to wear with leather leggings. Just be prepared that finding the right pair just might mean that you replace your favorite skinny jeans with them. From soft camel to rich brown to classic black, you can’t go wrong. Look for a pair with lots of stretch and a flattering high waist. This is a look that is sure to turn heads and enliven your outfits—day or night.

Ready to channel your inner rockstar? Sport your leather leggings with an oversized graphic tee. Top off this casual look with lace-up combat boots or high-top sneakers. Add a camo print cargo jacket and a slouchy carryall. The bigger, the better for this season’s on-trend streetwear bag.

Thinking about how to style leggings from desk to dinner with ease? A monochromatic look is your best bet. For a casual Friday, pair black leather leggings with over-the-knee boots and an oversized black sweater. This is the perfect canvas for colorful accessories. Beaded layering necklaces in different lengths and a coordinating clutch are all you need to dress up this outfit. Add a pop of color with a simple overcoat and swipe of bold lipstick to make a statement.

How To Wear Leggings To Work

Not ready to wear leather leggings to conquer your 9-to-5? Whether you’re working from home or the office, you can still end your workweek in a pair of leggings. When thinking about how to wear leggings to work, opt for Ponte leggings. Structured with stretch, this fabrication looks polished and professional. Style them with a jewel-toned tunic sweater. Elevate this office outfit with a boyfriend blazer and a pair of nude flats or leather slip-ons. 

For a meeting-ready look for the conference room or your next video chat, wear leggings with a crisp white button-down shirt. Opt for a slightly oversized silhouette to balance out the fitted leggings. Curious about how to wear leggings with layers? Tailored blazers or more casual denim jackets add structure and polish to your look. Another option that will add proportion and balance is by cinching your waist with a belt. Slip into slingback heels for a power pose that will lift your confidence to sky-high levels for your next presentation.

How To Wear Leggings With A Dress

Ever wonder how to wear leggings with a dress? It’s easier than it sounds, and it’s one of our no-fail style tips for colder weather. Next to leggings, one of our favorite wardrobe wonders has to be the perfect little black dress. A short black mini dress paired with black leggings is just waiting for the ideal accessories. For a casual look, style with ballet flats and a sweet locket necklace. Or, for a dressier vibe, wear this classic combo with a glittering statement necklace featuring colorful gemstones. Keep the earrings simple and choose black block-heels for understated allure.

Thinking about what to wear with leggings when the temperatures dip? Consider swapping your favorite tights for cozy leggings for extra warmth. You can wear a cashmere sweater dress with matching leggings and slouchy boots just about anywhere. Add a printed infinity scarf and a tote to put the finishing touches on this elegant winter look. 

What Shoes To Wear With Leggings

Shoes are the heart and ‘sole’ of any ensemble. They set the tone for your outfit, and should be equal parts comfortable and stylish. The key to deciding what shoes to wear with leggings depends on the occasion. From spring and summer sandals, sneakers and flats to fall and winter essentials like boots, loafers and heels, you can wear all of your footwear favorites with leggings. Keep reading to find out how to style leggings with your favorite shoes. 


This one’s a layup. When deciding what to wear with leggings, reach for a pair of kicks. For all of your loungewear, athleisure and performance legging looks, opt for lace-up and slip-on sneakers. On-trend for 2021, retro-style kicks still reign supreme. Athletic trainers in pops of neon color will work with your leggings for the hiking trail, gym or post office. Let your feet shine in a saturated hue while you run laps on the track, stroll to your next lunch spot or spring clean your apartment in style. 


The form-fitting nature of leggings easily slips into all kinds of boots with plenty of options to choose from. Pondering how to style leggings with a classic appeal? Reach for a boot that hits at the knee, while a daring over-the-knee style is seamless and sophisticated. Is your style a bit on the sassy side? An ankle bootie may be your preferred shoe choice. Let a little skin peek through between the bootie and hem of your leggings for flirty flair. We call this look sass-approved.


Practical and polished, flats never go out of style and are the perfect finishing touch when wondering how to style leggings. Choose from feminine ballet or d’orsay flats to menswear-inspired loafers. Minimalist flats are the ideal accompaniment to leggings. To keep things interesting, opt for a bold color or pattern. A bow or buckle is anything but boring (in our opinion), and can be the showpiece of your ensemble. 


For spring and summer, lighten up your leggings with sandals. From strappy gladiator styles to simple slides, all you’ll need is a fresh pedicure when pairing your leggings with sandals. Sporty sandals are one of this summer’s biggest shoe trends, and we are all for it. Here’s a quick tip for how to style leggings with sporty sandals: Pick a pair in a multitude of colors for a day exploring a new city. Complete the look with a tie-dye top (another summer 2021 trend we love), a moto jacket and a belt bag. Take a cue from the runways and wear your belt bag slung around your shoulder for a little extra street style cred.


Heels add grace and elegance and are the solution to your “what to wear with leggings” woes. From a chunky heel to a dainty kitten slingback to a power pair of pumps, you can’t go wrong with heels to elevate your legging looks. A short-stacked heel or stunning stiletto will make a statement, and have you putting your best foot forward. 

Are you loving leggings all over again? Take your style quiz, order a Fix and ask for new leggings to wear with your favorite tops, dresses and shoes. The more details the better—looking for classic black or are you ready to mix it up with a new style? Remember, shipping and returns are always free and no subscription is required.

A New Way To Shop

Stitch Fix connects you with personal Stylists to send you looks you’ll love.

Get Your Fix

Need expert fashion advice?

Get a personal stylist

Want more tips, trends & insider news? Follow @stitchfix on Instagram