10 Fashionable Fall and Winter Outfits With Black Leggings


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Whether they’re worn around the house, to the gym, or out and about, I can’t think of a single woman who doesn’t have a pair of black leggings. Not only are they more versatile than you think, but they’re also comfy, practical (perfect for adding extra warmth to your outfit on a cold day), and well, pretty much a wardrobe staple! Although this popular style is most often used for the gym or as loungewear, it can absolutely be elevated. My favorite type of outfits with black leggings are the ones that are chic, stylish, and cute. You too? Here are 10 fashionable black leggings outfits that will make you look put together in no time!

1. leggings + oversized chambray shirt + clogs + sunglasses + sling bag

outfits with black leggingsoutfits with black leggings

leggings | shirt | shoes | sunglasses | bag

Leggings are basically the ultimate comfort wear, but when you pair them with an oversized chambray shirt, you get this effortlessly chic vibe. The chambray shirt, with its relaxed fit and cool fabric, adds a touch of laid-back coolness. It’s perfect for those casual fall days.

Clogs, comfy and quirky, add a fun twist to the whole outfit. Finish off the look with some stylish sunglasses and don’t forget the sling bag. It’s practical, hands-free, and adds a final touch of casual flair.

This comfy and cute outfit is perfect for getting breakfast with friends, a casual day out, or even just running errands!

Related: 35 Must-Have Items for the Perfect Fall Wardrobe Checklist

2. leggings + basic tee or tank top + a long cardigan + loafers + tote bag

outfits with black leggingsoutfits with black leggings

leggings | top | sweater cardigan | loafers | bracelet | bag

Though the debate on whether leggings are pants is highly controversial, it’s true that leggings are thinner than most pants and don’t leave as much to the imagination. However, with a few styling swaps, they can still be worn for everyday wear with a bit of extra modesty. Enter the long cardigan!

The long cardigan, or sweater blazer, gives the ultimate casual look for when you want to be comfortable, yet put together. It not only adds a cozy appeal, but it dresses up your basics too.

These wardrobe staples – such as a white shirt, long cardigan, and (of course) classic black leggings – are all extra cozy, but elevated accessories like a tote bag and loafers add just the right amount of elegance. Be sure to pick high-quality, comfy fabrics and go for neutral colors to really get that more refined look!

3. leggings + sweater dress + boots + bucket tote

outfits with black leggingsoutfits with black leggings

leggings | dress | boots | bag

Oldie but goodie, sometimes a great go-to outfit formula doesn’t need any changes. This outfit combo is like the holy grail of comfort and style. You can always count on this look for the days that you want to look polished and put together.

The sweater dress feels like wrapping yourself in a warm hug all day long. Go for a chunky knit if you want that extra snug feel. Leggings are perfect for keeping things casual and are more comfortable than traditional tights. Plus, they give you that extra layer of warmth when it’s chilly out.

Let’s talk boots. Whether you go for ankle boots, knee-highs, or something in between, they add a touch of flair and make the outfit look more put-together. Ankle boots are great for a laid-back vibe, while knee-highs can add a bit of drama.

Lastly, grab a bucket tote. It’s roomy enough to hold all your essentials (and maybe a few non-essentials too) while adding a chic touch to your ensemble.

4. leggings + white tee + oversized blazer + ballet flats + crossbody bag

outfits with black leggingsoutfits with black leggings

leggings | blazer | flats | tee | bag | hoop earrings

Although leggings are usually associated with laid-back comfort, with luxe details, you can turn this look into one that’s street-style chic.

One great way to add style to a pair of black leggings (or any outfit for that matter) is with an oversized blazer. It’s the perfect way to add a touch of chic to your laid-back vibe, effortlessly blending comfort and style.

Pair it over a crisp white tee, because who doesn’t love a classic, clean slate to build an outfit on?

Slip into some cute ballet flats to add that French girl touch. They’re not just easy on the feet but also bring that polished yet relaxed feel to the ensemble. And to tie everything together? A handy crossbody bag. It’s not just practical, keeping your hands free and essentials close, but also adds a cute, casual touch to your overall look.

5. leggings + shorts + button-down + knee-high boots

outfits with black leggingsoutfits with black leggings

leggings | shorts | top | boots | bag

Style meets comfort meets chic. Start with your pair of leggings and then add a pair of shorts on top. Yep, you heard me right! Shorts over leggings give you that extra layer of warmth and a playful vibe.

Next, grab a classic button-down shirt. You can never go wrong with button-down tops. This timeless piece can pull the whole look together. Tuck it in or let it hang loose – your call!

Now for the pièce de résistance: knee-high boots. These babies are not only stylish but also perfect for strutting your stuff with confidence. They add a touch of sophistication and keep your legs cozy, too.

6. leggings + oversized sweater + jacket + boots

outfits with black leggingsoutfits with black leggings

leggings | sweater | jacket | boots | bag

This outfit is the definition of comfy cute and is perfect for those days when you want to look stylish without sacrificing comfort.

In this black leggings outfit, pair them with an oversized sweater for that cozy-just-rolled-out-of-bed-but-still-look-fabulous vibe. You can search specifically for sweaters with an oversized fit, or size up 1-2 sizes in the fall sweater you’ve got your eye on.

Throw on a trendy ranch/barn jacket or a classic denim jacket; it’s the perfect layering piece that adds a bit of edge to your look. Whether you go for a light wash or something darker, a denim jacket can make you feel effortlessly cool.

Finish off with a pair of boots – ankle boots, Chelsea boots, or even some knee-highs – the choice is up to you!

From running errands to grabbing coffee to hanging out with friends, this is a great casual look you can count on.

7. leggings + mini skirt + oxford + cashmere sweater + knee-high boots + watch

outfits with black leggingsoutfits with black leggings

leggings | skirt | sweater | boots | watch

A cute mini skirt over your leggings adds a playful vibe without being too over-the-top. And it wouldn’t be fall and winter without some layering – so on the top half start with an oxford or button-down shirt. It gives you that crisp, polished look, making you feel put-together even if you just rolled out of bed.

Layer on a cashmere sweater for that extra bit of coziness and luxe texture. Cashmere is soft, warm, and seriously chic, so you’ll feel like you’re wrapped in a cloud.

On your feet, knee-high boots are the way to go. They add a bit of edge and keep your legs warm, plus they look great with both leggings and skirts. Finally, finish off the look with a stylish watch. It’s the perfect accessory to tie this preppy chic together.

Related: 11 Chic Cashmere Outfits Styling Quince’s Best-Selling Cashmere Sweater

8. leggings + denim skirt + cardigan + socks + loafers

outfits with black leggingsoutfits with black leggings

leggings | skirt | socks | shoes | cardigan | belt

Perfect for fall, denim skirts have this way of making you look effortlessly cool, and when you pair them with leggings, you get the best of both worlds: style and comfort.

Next up, throw on a cozy cardigan. Whether you go for a chunky knit or something more lightweight, cardigans are like the Swiss Army knife of your wardrobe. They’re versatile, keep you warm, and add a touch of coziness to any look.

Let’s not forget about socks! Socks are a tiny but mighty way to express your personality and style. Not only do they add a quirky, stylish look, but they add extra warmth to your outfit.

Finish off with loafers. They’re classic, comfy, and add a polished touch to your outfit. Plus, loafers are perfect for almost any occasion, from brunch with friends to a casual day at the office.

9. leggings + trench coat + loafers + tote bag

outfits with black leggingsoutfits with black leggings

leggings | coat | loafers | bag

If you’re looking for a laid-back yet chic outfit, you can’t go wrong with this combo. It’s the perfect mix of comfort and style, making it ideal for a day out in the city or a casual lunch setting.

Leggings give you the freedom to move around while the classic trench coat on top gives you instant sophistication. Adding an elevated coat to your ensemble is an easy way to elevate even the most basic pieces. A trench coat in neutral colors is always a great choice! It’s timeless and works for almost any season, adding that touch of elegance to your look.

As far as footwear, loafers are your best friends here. They’re stylish, super easy to slip on, and comfortable for walking around town or running errands. Plus, they give the outfit a polished vibe without looking too formal.

Finally, the tote bag ties everything together (and brings it to the next level). It’s practical, spacious enough for all your essentials, and adds an extra flair to your ensemble. Whether you’re carrying your laptop, a book, or just your daily must-haves, a tote bag is a good choice.

10. leggings + long sleeve shirt + puffer vest + baseball cap + socks + clogs

outfits with black leggingsoutfits with black leggings

leggings | shirt | vest | socks | clogs | hat

When it comes to casual weekend attire, you can’t go wrong with this look! Pairing your leggings with a long-sleeved shirt keeps things casual but adds a bit of warmth, making it ideal for those unpredictable weather days.

The puffer vest adds the coziness of a warm hug without the bulk of a full jacket. Plus, it adds a stylish layer that’s both functional and fashionable. Throwing on a baseball cap? Classic move! It instantly gives off those laid-back vibes and can save you on a bad hair day.

Colored socks and clogs might sound unconventional, but trust me, it works. Socks keep your feet warm and cozy, while clogs are super easy to slip on and off, making them perfect for running errands or hanging out at home. This can be a great place to introduce a pop of color. You can also swap out the clogs for a pair of stylish sneakers. Altogether, this outfit is the epitome of comfort meets style!

How to Style Leggings in an Elevated Way

So, you’ve got a pair of leggings and you’re wondering how to make them look less gym-ready and more chic and polished? Of course, you can use all of the outfit ideas in this post, but I have even more easy tips to help you elevate your leggings game!

  • Choose High-Quality Fabrics: First things first, if you want your leggings to look a bit more luxe, opt for pairs made from high-quality fabrics. Think thick, opaque materials that offer a sleek finish. No see-through moments here!
  • Tunic Tops, Outerwear, and Oversized Sweaters: One of the easiest ways to dress up leggings is by pairing them with a longer top or chic layering piece. These longer tops not only provide more coverage but also add a touch of sophistication.
  • Blazers are Your Best Friend: Nothing says I’ve got my life together quite like a sharp blazer. Toss a fitted blazer over your leggings and a simple tee or blouse, and you’ve got yourself an instantly polished look. You can go classic with a black or navy blazer, or add a pop of color to keep things interesting.
  • Shoes Matter: Your choice of footwear can make or break your outfit. For a more refined look, swap out the sneakers for ankle boots, loafers, or even a pair of sleek heels. If you’re going for a more casual yet still elevated vibe, stylish flats or embellished sandals work wonders.
  • Accessorize: Never underestimate the power of good accessories! A statement necklace, chic scarf, or structured handbag can take your legging outfit from casual to classy in no time. Don’t forget a pair of stylish sunglasses for that added oomph!
  • Layer Like a Pro: Layering is another excellent way to add depth and sophistication to your look. Try a long cardigan over a fitted top, or throw on a cute denim jacket. The key is to mix textures and lengths for a balanced, stylish outfit.

Best Legging Styles & Brands

A high-waisted design offers comfort and style, providing a flattering fit that supports and shapes all body types.

Zella leggings are well-loved, especially the Studio Luxe High Waist 7/8 Leggings – they’re a standout! Reviewers say they’re buttery soft and super stretchy. Plus, they have a knack for staying put, no matter how intense your workout (or shopping day) gets.


For those who love a bit of luxury, Lululemon’s Align Pant is still reigning supreme. These leggings are crafted from their signature Nulu fabric, which is ridiculously soft and lightweight. It’s almost like wearing a second skin! They’re perfect for yoga, pilates, or just running errands in style.


On the budget-friendly side, Aerie’s Offline Real Me Leggings are ones to consider. They’re affordable, come in various lengths and styles, and are surprisingly durable. The fabric is smooth and stretchy, providing a great fit without breaking the bank.


For something a little different, consider the infamous faux leather leggings by Spanx. Not only does this unique texture add a little flair to your legging collection, but the cult favorite material sucks you in, offering a flattering and sleek shape. Even if you don’t choose a faux leather material, you can’t go wrong with the other Spanx Leggings.


For a sustainable pick, Everlane’s The Perform 24/7 Legging is hard to beat. These are the ones styled throughout this post and many reviewers have called them “the best leggings”. Soft yet thick, they can glide over any lower half imperfections, making you feel confident, supported, and stylish.


Stylish Outfits With Black Leggings

Whether you like casual outfits, dressy outfits, or somewhere in between, use this list of outfits with black leggings to not only help you find the perfect pair, but to style them too!

Looking for some more stylish and easy outfit ideas? Then you’re going to like this next post! Check out these 9 Easy Outfit Combinations You Already Have in Your Wardrobe

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