Edgy, Chic, AND Sexy! 15 Of The Best Tops To Wear With Leather Leggings

Leggings seem to be a polarizing topic!  Some of you love them and some of you really have a strong (I mean strong!) dislike for them. So, this post is for the legging lovers…and particularly the leather legging lovers! Leather or faux leggings can be cool, edgy, AND comfortable. They can elevate your outfits and are a lot dressier than workout leggings or even your standard cotton leggings. They are easy to style and can be super versatile to wear this fall/winter. Today we’re sharing a roundup of tops you can wear with leather leggings for running errands, looking chic with the girls for lunch, or looking a little extra sexy for date night or dinner.

Not sure you can wear leggings over 40 OR how to do so and still look chic and stylish? We share some of the basic dos and don’ts in this post.

15 Best Tops To Wear With Leather Leggings

We wanted to share the best sweaters and tops to wear with your leather leggings for maximum versatility. Full disclosure, Erin isn’t wearing leather leggings in all of these photos. The images are meant to spark some inspiration based on the style and fit of each top. You might even have similar tops hanging out in your own closet! But before we dive in, depending on where you live, the term “leggings” can sometimes be confused with “tights”. In the style world, these are 2 very different types of clothing…each has a different purpose and is styled differently. Make sure you check out this post if you need a little education or refresher on the difference between the two. Today we are definitely talking about leggings (not tights)! Further down in this post, we share Erin’s favorite leather and faux leather legging brands.

1) All Saints Sweater

The All Saints sweater Erin is wearing above might look familiar. It was a huge hit with so many of you during the NSale this year. It’s a medium-weight cashmere blend (despite what the online description reads), has an edgy, cool frayed hem, and a roomier silhouette. And, it’s also very soft! Depending on how tall you are, the length will hit around your upper thigh. So, it won’t completely cover your bottom, but paired with leather leggings you’ll have that slouchy relaxed fit on top to counteract the tighter fit on your lower half.

2) Oversized White Button-Down

In this look Erin is wearing the same oversized All Saints sweater from the previous look (in green!) but with an oversized white button-down layered underneath. The white button-down adds a bit more length…which we know some of you prefer. You could also ditch the sweater altogether and wear the button-down on its own or with a tank or cami layered underneath. The green sweater is unfortunately sold out, but it also comes in pink and black and we’ll link some similar green sweaters as well. We love how Erin styled this look with some edgy combat boots. We’ll be sharing some faux leather legging outfits and styling ideas below so just hang tight for those!

3) Free People Tunic Sweater

This ribbed knit tunic sweater from Free People has a loose mock neck (not at all constricting) and a slouchy fit with dropped shoulders. The length is perfect for wearing with leather leggings because it covers the bum. It skims the body with a relaxed fit but isn’t boxy or overly oversized.

4) Banana Republic Fuzzy Long Sweater

A pop of color will spice up your leather leggings! This beautiful cobalt blue Banana Republic sweater is one of those versatile knits you can easily throw on over your leggings. You can also style it with jeans, pants, joggers, or skirts. It has a longer length, a cozy mock-neck, and slouchy sleeves. The alpaca-blend knit fabric is also SO soft! Erin is wearing a small and it runs TTS, but it’s designed to fit more oversized. It also comes in petite.

5) Twofer Layered Cashmere Sweater

C by Bloomingdale’s Cashmere is an in-house Bloomie’s brand that makes amazing cashmere sweaters that are pretty much always on sale. This pre-layered sweater is SO chic, comfortable, soft, and versatile. And, will pair perfectly with leather leggings since the shirttail has a longer length. We love the layered look but trying to do it yourself can be annoying and actually add bulk. With a pre-layered sweater, it takes all of the guesswork out of it!

6) Open Edit Long Cardigan 

This longline cardigan from Open Edit can actually be worn open layered over leggings or all buttoned-up as a dress. We love a versatile piece like this one and you can’t beat the price at $89! Just add a sweater tank or cami underneath, and throw on some sneakers, booties, or slingback pumps with your leather leggings depending on how casual or dressy you want to look. We recommend sizing up one size on this one. It also comes in a pretty tan color.

7) Isabel Marant Mini Dress 

You’ll need to use your imagination a bit for this look, but a pair of black leather leggings would look amazing underneath this chic little mini dress by Isabel Marant Etoile. It looks almost brown in the photo but it’s actually a really cool faded black. We love the dramatic puff shoulders and super flattering ruching around the tummy. If the mini length is a bit out of your comfort zone, layering leggings underneath would be a cool way to confidently rock this 100% cotton, cozy LBD. Just add some black ankle boots and you’re good to go!

8) Staud Layered Sweater Dress

Along the same lines as the previous dress, this Staud layered-twofer dress would also look so chic layered over leather leggings. It’s a wool cable knit sweater with a slightly oversized fit. Can you picture it with some tall boots or over-the-knee boots? You can also wear it alone or with jeans…so it’s a super versatile piece!

9) Sleeveless Cashmere Turtleneck Sweater

Another great sweater to wear with black leather leggings is a sleeveless cashmere or knit turtleneck sweater. You can find one that has a longer, bum-covering length and front tuck it or leave it completely untucked. When it gets cooler, you can layer a cropped motto, leather, or denim jacket over the sleeveless sweater which will add some waist definition. Erin styled the sweater with some flared leather leggings (more on those below!) and some combat boots.

10) Cable Knit Sweater Vest

A chunky, relaxed fit cable knit sweater vest over leather leggings can be worn casually with combat boots or dressed up with booties. This look is so perfect for that fall weather when you want to breakout some seasonal pieces without being too warm. This sweater vest by Line & Dot is mid-weight with pretty ribbed detailing at the edges. Erin has it tucked in above, so the length is in fact a bit longer and will cover the bootie! And…it’s under $100.

11) Longline Wool Blazer

This is another look that requires a little imagination, but a longline blazer and tonal button-down blouse would be a chic but edgy way to wear leather leggings. This beautiful camel blazer by Banana Republic is such a great fall wardrobe staple. It’s a really soft wool that’s warm but breathable, has a little stretch, and is wrinkle-resistant. Erin is wearing a size small and it runs true to size. It also comes in tall and petite length. You could also try a boyfriend blazer or oversized blazer to achieve a similar look. Underneath the blazer, Erin is wearing a silk blouse in the same color family. This blouse is another wonderful basic to have in your closet and also comes in black and navy. Both pieces run true to size and come in petite!

12) High Slit Turtleneck Sweater

This is the coolest sweater by ASTR the Label. With its dramatic long length and slit it’s absolutely perfect to wear with leather leggings. It’s a really modern sweater that’s easy to style with blue or black jeans too. The weight is also perfect for fall…not too warm but not too cool. It runs true to size.

13) Boyfriend Cardigan

Can you picture how cute this boyfriend cardigan would look with leggings? In your mind, just swap out the fitted jeans Erin is wearing for leather leggings, and voila! This is one of those outfits that looks SO put together, but meanwhile, you are so cozy and comfortable. Love that!

14) Longline Cardigan

If you like the previous look but you’d prefer a longer cardigan that offers a bit more coverage, you could try something like a long, ribbed cardigan or even an oversized coatigan. We found a few that are very similar to the one Erin’s wearing in the photo above. You can wear a plain white tee, your favorite graphic tee, or a slim-fit turtleneck underneath.

15) Duster

Lastly, we wanted to share something you can wear with leather leggings that will take you right into the holidays! Whether you want to dress up your leather leggings with a sequin or velvet duster for a little holiday glam, or you prefer a warm cozy duster, the longer line silhouette is perfect for wearing over leather leggings. When you go with some of these longer tops and sweater options, you don’t have to worry about any insecurities you might have about lumps and bumps on your butt, legs, and thighs.

Best Leather & Faux Leggings

Now that you have some ideas for great tops and sweaters to pair with your leather leggings, let’s dig into the best leather and faux leather leggings we’ve found. Wearing them might feel a bit out of your comfort zone, but when you find a pair with built-in shapewear that helps smooth and contour, you can wear them confidently. Erin loves the Spanx faux leather leggings for this very reason. The fit is just TOO good. They also make pull-on leather pants if you prefer a wider leg silhouette, and leggings with a front slit to showcase a pretty shoe! On the right, SPRWMN is the brand behind the all-leather flared leggings. They have a high waist and a 29″ inseam so they’re the perfect length for Erin at 5’4″. Commando also makes a slim-fit faux leather jogger that offers just a bit more room than a traditional faux leather legging. All are excellent choices!

Leather Leggings Outfits

As promised above, let’s pull it all together so you can expertly style your leather leggings! These are outfit ideas you can keep in mind, so you’ll have some go-to looks at the ready. You can style them casually or dressier depending on your shoe choice, accessories, and the look you want to achieve.

Outfit #1) Faux Leather Leggings, Puffer Coat and Boots

We’re kicking things off with this super cute and casual outfit. Erin styled a pair of Carbon 38 foil sheen leggings (but faux leather leggings will work too!) with a black puffer jacket, some chunky Steve Madden Chelsea boots (always a best-seller!), a cashmere All Saints sweater, and some cool aviator sunnies. You could wear this look to a sporting event, running errands, or dashing out the door to pick up the kids from school.

Outfit #2) Leather Flared Leggings, Lady Jacket & Booties

This is more of an elegant and elevated way to style your leather leggings. Erin’s wearing the SPRWMN flared leggings we mentioned previously with a beautiful ruby red Alice + Olivia lady jacket, a black t-shirt, and some Schutz stiletto heel booties. This look would be SO chic for a holiday party or dinner out. The feminine jacket and edgy leggings are such a cool contrast!

Outfit #3) Faux Leather Leggings, Long Cardigan & Boots

Talk about expert layering! This next look is one from the archives, but it still looks so chic we just had to share it. Erin styled her faux leather leggings with a layered sweater top, a longline open-front cardigan, and some brown western-inspired boots. For accessories, she added a long necklace and a cool hat by Rag and Bone. This is an elevated casual look that is just SO cool! All the neutral shades of white, gray, black, and brown work together beautifully.

Outfit #4) Faux Leather Leggings, Layered Sweater, & Combat Boots

This is another older image, but the concept is still SO modern and on-trend today! Erin is wearing a Brochu Walker layered sweater that’s similar to the cashmere layered sweater in look #5 above. She’s wearing Spanx faux leather leggings and super edgy See By Chloe Combat boots that she’s had for years and breaks out every season. They are pricey but when you consider price per wear, these were a really great investment piece! She finished off the outfit with a gold chain crossbody bag which elevates her look and is a cool contrast to the boots!

Outfit #5) Faux Leather Leggings, Mini Dress & Sneakers

This last outfit idea includes a dress similar to the Isabel Marant Etoile dress Erin is wearing in look #7 above. She layered a black mini dress and leather moto jacket over her faux leather leggings and she’s wearing some cute sneakers to keep things REALLY comfortable. This would be such a chic look if you’re going to be walking around a bunch either on vacation, in the city, or even just for shopping!

Which of these outfit ideas is your favorite? Please share your thoughts in the comments below!

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