The Way To Wear Leggings This Fall, 50 Outfit Ideas

By Kaia Saunders / Updated on November 15, 2018

It’s a fall season, and leggings continue to reign supreme as far as fall fashion goes. Think about it, can you imagine going through fall without leggings? Neither can we!

Here are some of our favorite ways to rock this insanely comfortable yet stylish piece of clothing.

Stand Tall In Over-The-Knee Boots

Over-the-knee boots are perhaps the sexiest kind of boots in existence! At the same time, they can be a little bit intimidating as well.

So, if you’re unsure about how to style your over-the-knee boots, just throw them over a pair of leggings. Comfortable, practical, and stylish!

This monochromatic fall outfit with a graphic duster is super cute! Add brown boots for a touch of color, and you’re ready to dazzle!Photo: pinterest.com

This monochromatic fall outfit with a graphic duster is super cute! Add brown boots for a touch of color, and you’re ready to dazzle!

Even a simple outfit can look extra chic when you add over-the-knee boots.Photo: pinterest.com

Even a simple outfit can look extra chic when you add over-the-knee boots.

A long off-shoulder top looks fantastic with skinny leggings. Add matching boots to complete the all-black look.Photo: pinterest.com

A long off-shoulder top looks fantastic with skinny leggings. Add matching boots to complete the all-black look.

If blacks and browns are too dull for you, why not try grey suede over-the-knee boots with your leggings?Photo: bmodish.com

If blacks and browns are too dull for you, why not try grey suede over-the-knee boots with your leggings?

This edgy ensemble will make you look like the ultimate it-girl.Photo: pinterest.com

This edgy ensemble will make you look like the ultimate it-girl.



Stay Comfortable In Sneakers

Athleisure is THE trend to try this season, especially if you’re all about comfortable fashion. So, get inspired by these lovely ladies and get your sneakers on!

Stand out from the army of white and black sneakers by throwing on pink converse shoes with black leggings.Photo: pinterest.com

Stand out from the army of white and black sneakers by throwing on pink converse shoes with black leggings.

Let’s face it, ladies - you simply cannot go wrong with a white tee, black leggings, and white sneakers. Add a beautiful beige duster for a feminine touch.Photo: pinterest.com

Let’s face it, ladies – you simply cannot go wrong with a white tee, black leggings, and white sneakers. Add a beautiful beige duster for a feminine touch.

This model-off-duty look is all kinds of cool!Photo: pinterest.com

This model-off-duty look is all kinds of cool!

A sporty tee with sneakers and leggings? Yes, please! Add a long jacket to look really sharp.Photo: fashiongum.com

A sporty tee with sneakers and leggings? Yes, please! Add a long jacket to look really sharp.

For a relaxed weekend look, try pairing a striped tee with a denim jacket, white sneakers, and a circle scarf.Photo: pinterest.com

For a relaxed weekend look, try pairing a striped tee with a denim jacket, white sneakers, and a circle scarf.

Add Some Length

There was a time when wearing leggings as pants was frowned upon. While those days are long gone, some women still think twice about following the leggings trend.

If you’re one of these women, we’ve got a simple solution. Just pair your leggings with a long top or tunic. Not only will you be comfortable but the long top will add length to your silhouette and make you seem taller than you are. Win-win!

Mustard and black work so well together! Pair your flowy mustard top with black leggings and black ankle boots.Photo: glamasia.com

Mustard and black work so well together! Pair your flowy mustard top with black leggings and black ankle boots.



Now that’s how you do fall in style.Photo: pinterest.com

Now that’s how you do fall in style.

Printed leggings are a remarkable change from boring solids. Add a top with a drapey effect and brown boots to truly stand out.Photo: pinterest.com

Printed leggings are a remarkable change from boring solids. Add a top with a drapey effect and brown boots to truly stand out.

For a boho-inspired fall look, try a printed tunic like this one with plain black leggings and open toe boots. Gorgeous!Photo: pinterest.com

For a boho-inspired fall look, try a printed tunic like this one with plain black leggings and open toe boots. Gorgeous!

Add some drama to your black and white look with a checkered scarf, a long cardigan, and brown boots.Photo: pinterest.com

Add some drama to your black and white look with a checkered scarf, a long cardigan, and brown boots.

Bring Out Your Skirts

As far as we’re concerned, it’s always skirt season! Thankfully, skirts look great with leggings when styled right. Check out these fabulous inspirations.

Give your mini skirt a fall makeover by pairing it with thick black leggings and an oversized sweater.Photo: pinterest.com

Give your mini skirt a fall makeover by pairing it with thick black leggings and an oversized sweater.

Take a cue from this sartorialist on how to stand out in a crowd. Pair a golden skirt with blue leggings, golden shoes, black top, and a bright yellow jacket. This is certainly not for the faint-hearted!Photo: Instagram/@allwomenstalk

Take a cue from this sartorialist on how to stand out in a crowd. Pair a golden skirt with blue leggings, golden shoes, black top, and a bright yellow jacket. This is certainly not for the faint-hearted!



If you’re a fan of subtle fashion, try this nude and cream look.Photo: pinterest.com

If you’re a fan of subtle fashion, try this nude and cream look.

A thick skirt is perfect for fall. Wear yours with a sweater top, leggings, and a knit scarf.Photo: pinterest.com

A thick skirt is perfect for fall. Wear yours with a sweater top, leggings, and a knit scarf.

Don’t shy away from wearing an animal print skirt during fall. Pair yours with a chunky knit top, a black jacket, and black booties. Add a bright orange clutch and voila!Photo: pinterest.com

Don’t shy away from wearing an animal print skirt during fall. Take inspiration from Olivia Palermo and pair yours with a chunky knit top, a black jacket, and black booties. Add a bright orange clutch and voila!

Try Statement Looks

You can either choose to play it safe or experiment with your looks and stand out like a diamond.

Since fashion is all about pushing the envelope, we recommend the latter. Why not give these statement legging outfit looks a try?

This look is a true statement from head to toe! We love the bright pink faux fur, the patent leggings, and the metallic silver boots. Would you dare to recreate it?Photo: Instagram/@allwomenstalk

This look is a true statement from head to toe! We love the bright pink faux fur, the patent leggings, and the metallic silver boots. Would you dare to recreate it?

Of course, statement looks don’t always have to be in your face. Try something like these lace-up leggings with metallic boots to make a subtle yet powerful statement.Photo: pinterest.com

Of course, statement looks don’t always have to be in your face. Try something like these lace-up leggings with metallic boots to make a subtle yet powerful statement.

Adding a statement purse to a classic, feminine look is always a winning idea!Photo: popsugar.com

Adding a statement purse to a classic, feminine look is always a winning idea!



A ripped crop top with printed leggings is a daring look. Add a blazer to pull the look together.Photo: pinterest.com

A ripped crop top with printed leggings is a daring look. Add a blazer to pull the look together.

Pair checkered leggings with a plain beige sweater top to look fall ready!Photo: pinterest.com

Pair checkered leggings with a plain beige sweater top to look fall ready!

Say Yes To Slouchy Sweaters

Fall is as much about comfort as it is about fashion and nothing is more comfortable than your trusty slouchy sweater. Plus they always look great with a pair of leggings! Ready to check out some of our fall favorites?

Don’t you just love this slouchy sweater with flute sleeves? Add black pumps and red lipstick for that perfect lunch date look.Photo: pinterest.com

Don’t you just love this slouchy sweater with flute sleeves? Add black pumps and red lipstick for that perfect lunch date look.

Time to get back to the basics with an oversized turtleneck sweater, black leggings, and black boots.Photo: pinterest.com

Time to get back to the basics with an oversized turtleneck sweater, black leggings, and black boots.

For an edgier yet comfortable look, try a graphic sweater with rolled up leggings and booties!Photo: pinterest.com

For an edgier yet comfortable look, try a graphic sweater with rolled up leggings and booties!

Ladies we’ve got some news for you. Stirrup leggings are back and how! Pair yours with a statement royal blue sweater and heels!Photo: pinterest.com

Ladies we’ve got some news for you. Stirrup leggings are back and how! Pair yours with a statement royal blue sweater and heels!

This preppy look with a thick knit sweater is perfect for anyone!Photo: pinterest.com

This preppy look with a thick knit sweater is perfect for anyone!

Anchor It With Ankle Boots

Ankle boots and leggings go together like Blake Lively and Ryan Reynolds. You can always easily tuck your leggings into ankle boots, and they always look oh-so-good together. What more could you want?

These embossed ankle boots are fierce, and that jacket just takes it to the next level.Photo: m.55bbs.com

These embossed ankle boots are fierce, and that jacket just takes it to the next level.

Channel your inner Wednesday Addams in this all-black outfit.Photo: weheartit.com

Channel your inner Wednesday Addams in this all-black outfit.

Trust us - you can’t go wrong with this combination.Photo: pinterest.com

Trust us – you can’t go wrong with this combination.



These leopard print ankle boots add a fun touch to an otherwise ho-hum look.Photo: pinterest.com

These leopard print ankle boots add a fun touch to an otherwise ho-hum look.

Don’t be afraid to embrace color when it comes to leggings.Photo: pinterest.com

Don’t be afraid to embrace color when it comes to leggings.

Layer It Up

Layers not only keep you warm but they are are also a great way to rehash your summer clothes for fall. Check out some of these fun layered outfits that you can rock with your leggings.

This muted yet sexy layered look is perfect for fall. Add a sparkling touch with glitter booties.Photo: popsugar.com

This muted yet sexy layered look is perfect for fall. Add a sparkling touch with glitter booties.

Casual chic is the way to go this fall! Try wearing an oversized sweater over your denim shirt and leggings to stay warm and look cool at the same time.Photo: pinterest.com

Casual chic is the way to go this fall! Try wearing an oversized sweater over your denim shirt and leggings to stay warm and look cool at the same time.

Graphic tees are everywhere right now. Layer yours with black leggings, a black jacket, and a cute beanie.Photo: dicasdemulher.com.br

Graphic tees are everywhere right now. Layer yours with black leggings, a black jacket, and a cute beanie.

Now, this is a classic look for fall!Photo: pinterest.com

Now, this is a classic look for fall!

How adorable is this layered fall look?!Photo: thedashofdarling.com

How adorable is this layered fall look?!

Girly Dresses

If you’re one of those women who hates saying goodbye to dresses during fall, fret not for we have the perfect solution. Look ahead!

This look is so incredibly sexy and well put together! Adding a belt like that will not only cinch in your waist but will also add a unique touch to your look.Photo: pinterest.com

This look is so incredibly sexy and well put together! Adding a belt like that will not only cinch in your waist but will also add a unique touch to your look.



This short dress paired with leggings and high heels is perfect for a night out.Photo: Instagram/@gutierrezary

This short dress paired with leggings and high heels is perfect for a night out.

Animal print dresses look classy with leggings and lace-up boots.Photo: pinterest.com

Animal print dresses look classy with leggings and lace-up boots.

Give your white summer dress a new lease of life by wearing it with leggings, boots, and a leather jacket.Photo: pinterest.com

Give your white summer dress a new lease of life by wearing it with leggings, boots, and a leather jacket.

This look is super elegant from head to toe!Photo: memorandum.com

This look is super elegant from head to toe!

Loud And Clear In Leather Leggings

Spice up your fall look in faux leather leggings. They’re super on trend, super stylish, and sexy!

Add a twist to the classic black and white combo with a pair of black faux leather leggings.Photo: truthorflares.com

Add a twist to the classic black and white combo with a pair of black faux leather leggings.

Look sharp in this black outfit complete with a blazer.Photo: thefashiontag.com

Look sharp in this black outfit complete with a blazer.

There’s something about a blazer that adds instant sophistication to any look. Brown open toe boots add a nice contrast to this black and white look.Photo: thefashiontag.com

There’s something about a blazer that adds instant sophistication to any look. Brown open toe boots add a nice contrast to this black and white look.



This darling combination is perfect for work and play.Photo: fashiongum.com

This darling combination is perfect for work and play.

Colored leather leggings are something else!Photo: pinterest.com

Colored leather leggings are something else!

We hope this post has inspired you with many different ideas on how to wear leggings this fall. Which one was your favorite?


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