Last Updated on October 5, 2023 by Eve Dawes
How to style leggings | 20 leggings outfit ideas from everyday casual to date night leggings outfits
Leggings outfits can get repetitive, so I’m sharing 20 ways leggings outfit ideas to keep them on repeat and your look fresh. Along with the do’s and don’ts of what to wear with leggings. Are leggings still in style? Here’s 20 on trend, cute leggings outfits for all occasions and seasons. Black leggings are one of those wardrobe essentials we all tend to throw on for everyday comfort and casual outfits but it’s easy to get stuck in a rut. I know I’ve been guilty of falling into the habit of styling them the same way: sweater dress and boots. I think most of us do; whether thats sneakers and a tee or sweater dress. So here’s more ways on how to style leggings for 2023 and to solve what to wear with leggings for both casual and fashion forward outfits.
I’ve had to get more creative with how I style leggings as I wear them a lot for work and traveling as I like to pack as lightly as possible. These are the my go to leggings outfits, including what to wear with leather leggings that easily take them from day to night, casual to dressy. If you’re wondering if leggings are still in style for 2023 read on.
Jump to shop the most flattering on trend leggings.
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Are leggings still in style for 2023
If you’re wondering if leggings are still in style for 2023, it’s more about the type of leggings and how you style them that makes them in fashion or out. I’ve rounded up some of my favorite leggings outfit ideas from Instagram. With ways to wear leggings in 2023 that are both dressed up and down. As well as from the fashion shows, like the neon logo leggings as seen at Gucci.
Leggings are one of those wardrobe essentials that always come back into rotation but they were seen in more fashion shows this season than in a while. So yes, leggings are still in style for 2023 but it all comes down to how you style them.
What to wear with leggings? 27 leather pants and leggings outfit ideas
Leggings can be styled a lot of the same ways as you’d style your fitted leather pants. Here’s lots of outfit ideas from casual and classic to glam, classic style to what’s trending now and influencer inspired leggings outfit ideas.
1. Black leggings outfit | Create a monochromatic look with black leggings and black accessories
If you’re wondering what to wear with leggings in 2023 for an on trend, sleek and chic look create a monochromatic black leggings outfit with black leggings, black high heel pumps, a black structured coat and up do. It gives total power player vibes. A high neck and high heels are great if you’re petite and want to create a more elongated look.
This is such a laid back, cool girl, street style with the oversized blazer and baseball cap. Style leggings with a cropped sweater or half tuck your sweater at the front for the same effect.
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Shop the monochromatic leggings outfit look
Monochromatic outfits are a big trend for 2023. As well as monochromatic outfits broken up with white sneakers. These pieces will help you create a timeless neutral or black leggings outfit.
2. What to wear with leggings for Winter 2023?Winter leggings outfit idea
What to wear with leggings in Winter? Luxe textures & geometric prints work great for Winter. Think cozy, soft, black velvet leggings and trending geometric prints like tartan are perfect for creating a festive look and layering up for Winter 2023.
There’s something about black velvet leggings that add a luxe touch to any leggings outfit and this stretch fit pair are under $120. Styling them with a turtle neck top and faux fur gilet is perfect for colder months and tartan gives it a festive look.
Tartan is a classic Winter trend that Vivienne Westwood, Alexander McQueen and Holland and Cooper always do so well.
Shop the geometric leggings outfit look
Add a pop of color or a bold print to your black and neutral leggings to brighten up your look and create more contrast.
3. What to wear with leggings for warmth | Long length sweaters and leggings
I’m kind of a believer that most leggings aren’t really completely pants / trousers and need a longer length top if certain things show. Unless they are thicker material or leather leggings, have a detailed waistline, or aren’t too tight on the crotch for obvious reasons.
It’s an easy casual leggings outfit idea that looks just as good with sneakers as it does with boots of any length. It’s also an easy way to style bright, neon or logoed leggings to let them be the statement piece.
Shop what to wear with leather leggings
Sexy leather leggings, chic knee high boots and the coziest long length sweaters to wear with leggings.
4. Wear leggings under dresses and sweater dresses
Probably one of the most most worn looks and an easy way to be able to wear dresses later into the season. I tend to go from bare leg to tights to leggings as it gets cold to get the most wear out of my dresses and sweater dresses. It’s one of those cute leggings outfits that will always be in style and sweater dresses are back in fashion in a big way for Fall Winter 2023-2024.
5. Smart casual leggings outfit idea
Leggings, high heel pumps, a structured coat and up do give total power player vibes. A high neck and high heels are great if you’re petite and want to create a more elongated look.
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Shop the smart casual leggings look
Sophisticated long structured coats for an elegant look.
6. Cozy leggings outfit | With a faux fur jacket
This is such a cozy, comfy and cute outfit with leggings look for Fall & Winter for running errands, eating all of your Christmas favorites and holiday shopping. Faux fur coats are another Winter trend for 2023 and normally super affordable.
I’m such a boots addict, so they tend to be my go to with leggings in Fall and Winter rather than sneakers. This cozy faux shearling coat was also on repeat a lot last year as it’s so warm and goes with everything. So it’ll definitely get worn a lot again this year and comes in other colors if you don’t trust yourself with white!
Shop what to wear with leggings | Cozy faux fur coats
The coziest faux fur and teddy coats to wear with leggings in 2023 on cold days.
7. Warm winter leggings outfit | Style leggings with a puffer coat
Wear your leggings with this Winters coziest and most practical trend, a puffer jacket. The bigger and puffier the better. This doesn’t just have to be a black leggings outfit, so don’t be afraid of bright colors. As vibrant colors were all over the Fall Winter runways.
It’s a look that’s easy to layer and works with all leggings from leather to bold prints and colors.
Shop puffer coats
These fashion forward puffer coats are perfect for staying warm and a cozy look to keep your leggings on repeat through even the coldest months.
8. Style them with a longer length top
This is such a versatile look that’s easy to layer without creating bulk from season to season. I love belted versions of this style to break up a mass of color and add my own personality to the leggings outfit. Plus a belt can instantly dress up a simple leggings and top outfit.
For the most flattering look, go for an all black leggings outfit. Then just add high heel boots or pumps to take this look from day to night. If you’re wondering what to wear with leather leggings this is a great way to play with mixing different textures.
9. What to wear with leggings in 2023 for work | Office appropriate leggings outfit with a blazer dress
If you’re wondering what to wear with leggings to work and if they’re even office appropriate, they totally can be. Wear leggings with a blazer or blazer dress to make leggings office appropriate or at least Zoom call appropriate.
10. Cute leggings outfit | Layer a denim jacket over a cropped t-shirt
A cropped top on its own with leggings can look a bit too much like you’re headed to workout. However, layered with a cropped jacket it looks more streetwear than gym wear and is an on trend and super cute leggings outfit idea. If crop tops aren’t in your comfort zone, this look works just as well with a simple white tee half tucked at the front.
11. Casual leggings outfit | Athleisure wear
For an easy everyday outfit whether it’s actually to workout or just to run errands, style your leggings with a sports bra or tank top, baseball cap and sneakers. Layer up as needed and accessorize it whatever way suits your mood and personal style.
12. Everyday casual leggings outfit idea
If a sports bra or crop top is too much skin, swap those out for a plain white t-shirt. It’s simple but classic and timeless.
13. Just add leather
To make idea number 12 work on cooler days just add a cool leather jacket for an edgy look. Styled with either sneakers or leather boots if you want something a bit less casual
14. Coordinated chic leggings outfit idea | Matching sets
Lots of leggings are now sold as matching sets. From super cute long sleeve crop tops to knit sets and smarter tailored tops. If you’re looking for something bold and colorful, check out Versace Couture’s matching leggings and top set. For something more chic, this beige outfit is a great option.
15. Trending leggings outfit 2023/2024 – UGG’s are back
If you’re wondering what to wear with leggings for the most in style leggings outfit for Winter 2023-2024 UGGs are back! They’ve been flying off the shelf from the mules to the boots. Comfortable and warm, I’m happy to see the return of these cozy boots this season.
16. Retro style trending leggings outfit
Another trending way to style your leggings this season is with a classic crew neck sweater. Anine Bing makes some great ones. Yes, sweaters and leggings are a go-to style so to keep it fresh this season stick to crewneck, vintage styles with white sneakers.
17. Warm black leggings outfit
To add even more warmth to leggings outfit idea No. 14 layer a roll neck sweater under your sweatshirt. Like this but swap the black jeans for leggings. If you prefer to cover certain areas, just opt for a longer length sweatshirt.
18. What to wear with leggings in 2023 | Get slouchy
Slouch socks are still in style for 2023 and work really well with the crewneck sweater and sneakers leggings outfit to create that retro Diana era aesthetic. It doesn’t matter what color they are, as long as your slouchy crew socks hit around the ankle it’s an instant way to create a cool girl aesthetic.
19. Pumpkin Spice Latte girl | Fall leggings outfit idea
For Fall a long tank top layered under a duster jacket works well. Just add a wide brim hat for the full Pumpkin Spice Latte girl aesthetic. If this look is getting a little tired to you, swap the hide for a wide headband for a cute leggings outfit that’s so in right now.
20. Airport outfit
Leggings are one of my go-to’s for flying but to keep it a little less athletic and a little more chic swap sneakers for loafers and style them with a loose flowy top, oversized scarf and XL tote bag.
21. Wild thing
To add interest to an all black leggings outfit, try an animal print scarf, jacket, heels or bag. Just not all at the same time!
22. Chic Winter leggings outfit idea
Style them with a long length turtleneck or roll neck sweater and heeled ankle, knee or over the knee boots for a sleek, chic look.
Best leggings for a flattering fit
These are my favorite leggings (linked below) that are on trend, flattering and easy to style any of the ways above. If you have issues with leggings rising up, go for a pair of stirrup leggings. Yes, they’re back, along with patent leather leggings and many other trends from the 80’s but with less hair teasing.
Another leggings trend is split hems which make them a little different and looks great with heels. Some of my favorite styles right now are on Revolve, especially their patent styles.
Don’t think that they have to be just neutral or black, there’s lots of plaid, as well as sexy cut outs, sheer styles and embellishments to have fun with this style and to create more fashion forward, statement outfits with.
Shop best selling womens leggings
From designer leggings to pairs under $30 there’s a color, material and style for everyone in this curated list to create your cute leggings outfit ideas with. If you’re looking for the most support and flattering fit, it’s hard to go wrong with Spanx who now also do seamless leggings which don’t leave marks when you change into a skirt or dress for the evening.
Lulu Lemon tend to be good for both quality and function and ASOS is good if you need either petite or tall collections. If you’re looking for designer leggings, I’ve rounded more of those up in a separate article.
If you shop from Italist, don’t forget to use code RF-220X-D9218D at checkout for a chance to win $500.
Are leggings in style for 2024?
Yes, leggings are still in style for 2024. They’re one of those wardrobe essentials that can always be styled to be in style. They’re quickly going from functional fashion to chic, fashion forward, on trend items and designer leggings with heels are popping up everywhere.
The material of leggings in fashion tends to change. For your 2024 leggings outfit leave the plain cotton lycra material for the gym or grocery store. For the street, go for leather, faux leather, suede, split hem or printed leggings for a more fashionable and less athleisure wear look for 2024.
What not to wear with leggings?
5 don’t and things to avoid wearing with leggings:
- Bodysuits that aren’t thongs to avoid VPL.
- With underwear that creates VPL.
- Gym bags unless you’re going to the gym.
- Instead of just wearing sports bras with leggings unless you’re working out try crop tops and layer with a denim jacket or long line cardigan or blazer to make the look more streetwear and less gym wear.
- Shiny thigh high boots with shiny or PU leggings and short tops unless that’s the look you’re going for. It just doesn’t work for most of us for everyday.
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