Leggings are easily one of my most-worn pieces of clothing.
I can’t help but reach for them when I’m heading out to run errands, hanging out at home, or meeting up with my friends for a casual day.
They’re comfy, stretchy, and honestly look good with pretty much anything I own.
The best part is how you can easily mix and match them to fit different vibes—whether I want to look laid-back or a little more put together, leggings always come clutch.
I’ve played around with so many outfit combinations and figured out some staple looks that never fail.
So, I’m here to share some of my favorite ways to style leggings and still feel super cute and comfortable all day.
Dressy Outfits with Leggings
Leggings aren’t just for any day of the week—they can easily be styled for dressier looks too.
With the right shirt, a structured jacket, and a few accessories like vintage necklaces, leggings can turn an outfit that feels both polished and comfortable.
You can pair them with heels or a statement piece like a jacket and can make your drab outfit into a dressy and elegant one.
Here are some dressy outfit ideas with leggings that balance chic style and ease perfectly.
1. Leather Leggings Paired With Chunky Boots
The fiery vibe from leather leggings mixed with the strong look of chunky boots is definitely a winning combo.
You could wear this leggings outfit when heading to a concert, brunch, or just want to look cute.
Throw on an oversized sweater or a graphic tee with a jacket to balance it out, and you’ve got yourself a cute and elegant leggings outfit.
To ace this look, mix textures and keep things bold yet laid-back.
Leather leggings and chunky boots just elude confidence while keeping you comfy and stylish at the same time.
2. Oversized Sweater + Leggings and Slides
I love this look!
Oversized sweaters, leggings, and slides make such an easy, laid-back outfit that’s perfect for everyday athleisure wear.
The oversized sweater gives that carefree look, while leggings add a sleek, fitted vibe to make a cute outfit.
Slides or mules keep things casual and comfortable, making it a solid choice for running errands or meeting up with friends.
You can add a crossbody bag or some subtle jewelry to give it a little extra style without overdoing it.
It’s the kind of outfit that feels put together but still really comfortable, perfect for when you want to look good without spending too much time planning.
3. Tall Boots + Leggings
Wearing boots and leggings are a classic pairing that works for almost any occasion. The sleekness of leggings with tall boots gives your outfit a comfortable feel.
This leggings outfit is best for a casual day out or if you want to dress up a bit.
Add some accessories like a scarf or bag to elevate the look without too much effort. It’s an easy, stylish way to stay cozy and chic.
4. White Leggings + Pink Sweater
White leggings paired with a pink sweater create a soft, fresh look that’s made for a casual day out or even a cozy night in.
The brightness of the white leggings makes them noticeable, while the pink sweater adds a pop of color without being too crazy.
It’s all about balancing light, airy tones with a comfortable, stylish vibe.
Throw on some cute sneakers or slides, and you’ve got an easy, pulled-together outfit.
Whether running errands or grabbing coffee with friends, this look keeps things fun and simple while still feeling put-together and trendy.
5. Buttoned Down Shirt + Black Leggings
Black leggings keep things sleek and fitted, while the button-down adds a touch of structure to balance it out.
You can wear this for a more put-together look for a lunch date or you can keep it relaxed for a day out.
You can tuck in the shirt for a clean, streamlined vibe or leave it loose for a laid-back feel.
Pair it with ankle boots or sneakers, depending on your plans, and you’re set. Add some accessories, like a belt or simple jewelry, to elevate the outfit without making it look overdone.
6. Grey Leggings + Knee-High Boots
Knee-high boots instantly take grey leggings from casual to chic, creating a look that’s both elegant and comfortable.
The neutral tone of the grey leggings pairs perfectly with the boldness of knee-high boots, making it an easy go-to for fall or winter outfits.
You can throw on a long cardigan or oversized sweater for a cozy feel, or opt for a fitted jacket for a more polished look. This combination works for everything from casual outings to weekend brunches, blending comfort with style without trying too hard. Add a scarf or a simple crossbody bag to complete the look.
7. Maroon Leggings + Plaid Sweater and White Top
Layering a white top under a plaid sweater is such a vibe, especially when paired with maroon leggings.
The rich color of the leggings adds a bold contrast to the softer tones of the sweater and top, making this outfit a great choice for fall or cooler days.
You can finish the look with ankle boots or even some cozy sneakers, depending on the occasion. Whether you’re headed out for a coffee date or just running errands, this combo keeps things comfortable without sacrificing style.
The plaid sweater adds a touch of pattern while the white top lightens up the look, creating a balanced outfit that’s perfect for the season. Add some simple accessories for extra flair!
8. Fall Checkered Dress + Leggings
The checkered pattern gives off cozy fall vibes, while the leggings add warmth and make the outfit more versatile.
Whether you’re going for a casual day out or want something a bit more put together, this combo works for almost any fall occasion.
The dress goes well with black or neutral leggings to keep the focus on the checkered print, and finish the look with ankle boots or knee-highs, depending on your style.
If it’s a chilly day, layer a denim jacket or oversized cardigan on top to add extra warmth without losing that autumn feel.
This outfit strikes the balance between cozy and stylish, making it easy to wear whether you’re apple-picking, hitting up a fall festival, or just enjoying a crisp day out.
9. Leggings + Flats
Leggings with flats make for an easy outfit to wear for every day of the week.
Flats adds a touch of style while keeping things comfortable and easy to move in.
This outfit with leggings is great for running errands, meeting up with friends, or just going about your day.
You can dress it up with a flowy blouse or keep it casual with a comfy sweater. It’s a go-to look that blends comfort with just the right amount of style for any laid-back day.
Outfits with Grey Leggings (9)
Grey leggings are low-key underrated, but they’re super easy to style.
They go with almost anything since they are a neutral color and give off that, put-together look without trying too hard.
They’re not as basic as black, so you can mix them up with different colors and textures.
Ready to check out some cool outfit ideas to make your grey leggings pop? Let’s get into it.
10. All in Grey
To get the fullest of your grey leggings try going all grey.
This is a sleek, minimalist outfit, and always looks good without being too flashy.
Throw on a grey hoodie, and you’ve got an easy monochrome look that’s chill but still feels like you put some thought into it.
You can mix up the textures, like pairing soft cotton leggings with a knit sweater or a puffer jacket.
Add some silver jewelry or chunky sneakers to break it up a bit. It’s all about keeping it clean and simple while letting the neutral tones do the work.
Grey on grey always hits differently when you want to keep things low-key but stylish.
11. Plaid + Grey Leggings + Hiking Boots
When you don’t have time to dress up, then put together this leggings outfit.
Plaid with grey leggings and hiking boots is the perfect mix of outdoorsy and laid-back style.
The plaid adds some texture and color, while grey leggings keep things simple and neutral.
The hiking boots give the look a rugged edge, making it perfect for fall hikes or just running errands.
It’s all about comfort with a little bit of style, and the combo feels effortless while still looking like you’ve got it together.
12. Casual Sweatshirt + Grey Leggings
For the ultimate athleisure outfit go with a casual sweatshirt paired with grey leggings.
The relaxed look of a sweatshirt makes it perfect for lounging around or running errands, while grey leggings offer a clean and neutral base that goes with anything.
You can choose an oversized sweatshirt for that cozy, feel or a more fitted option if you want to keep it simple. Add some Dunks or Uggs, and you’re ready to take on the day without much effort.
13. Pink Sweater with Grey Leggings
For a softer look, pairing a pink sweater with grey leggings is a perfect choice.
The grey leggings balance the brightness of the pink sweater, creating an outfit that’s both warm and stylish.
You can keep it casual with Nike’s or dress it up a bit with Chelsea boots for a slightly elevated vibe.
Adding a crossbody bag or minimal jewelry gives just enough style without trying too hard.
This outfit is great for casual outings, running errands, or even a laid-back brunch with friends.
14. Burgundy Sweater + Leggings
To dress up your grey leggings try wearing a burgundy sweater.
The deep, rich color of the sweater adds a pop of warmth to the look, while leggings keep it laid-back and easy to wear.
You can go for an oversized sweater for a more relaxed vibe or a fitted one for a cleaner look.
Pair this combo with ankle boots or sneakers, depending on how casual or dressed up you want to be.
Throw in some simple accessories like a scarf or a beanie to complete the outfit, making it a go-to for cozy days out.
15. Blue Top + Grey Leggings + Brown Boots
For a day out, pairing a blue top with grey leggings and brown boots creates a fall vibe with your fall nail colors.
The grey leggings act as a neutral foundation, letting the blue top stand out and bring some color to the look.
Brown boots add a nice earthy contrast, grounding the outfit while keeping it casual and chic.
You can choose a fitted blue top for a more polished vibe or go with a relaxed, oversized one for a laid-back feel.
A simple scarf or tote bag can add an extra touch without feeling overdone.
This combo is perfect for running errands, meeting friends, or enjoying a weekend day out, blending comfort and style for a versatile look.
16. Grey Leggings + White Top + Jacket
If you want a more athletic look, try paring grey leggings with a white top and a jacket.
The grey leggings offer a neutral base that pairs perfectly with the clean look of a white top.
Wear a lightweight jacket to add an extra layer of style and functionality.
Finish off the look with some sneakers and a simple cap for that athletic, on-the-go feel. It’s an easy, comfortable outfit for casual outings or running errands.
17. Grey Leggings for a Workout Outfit
If you want to work out in style, grey leggings are a great option for both comfort and versatility.
The color allows you to pair them with just about any workout top, from bright tanks to simple black tees.
Grey leggings are also great for showing off the details of your favorite athletic shoes or sneakers.
The stretchy, form-fitting material keeps you comfortable while you move, making them perfect for everything from yoga to running or strength training.
Add in a pair of supportive sneakers and you’ve got yourself an easy, go-to workout outfit that looks good while keeping you ready for whatever your exercise routine throws your way.
18. Green Dress + Grey Leggings
For a dressy look, pairing a green dress with grey leggings offers the perfect mix of style and comfort.
The rich green adds a pop of color, while the grey leggings keep things neutral and balanced.
This fall outfit combo works well for cooler weather, giving you an outfit that’s both cozy and chic.
You can dress it up with ankle boots or even heels, depending on the occasion.
Add a belt to cinch the waist or a statement necklace for a bit of flair. It’s an easy way to elevate a simple dress while staying comfortable throughout the day.
The Best Outfits with Leggings
Leggings are seriously the best swap for jeans—still neutral but way softer, giving your outfit that fresh vibe.
You can style them with anything, whether it’s an oversized hoodie, a cute top, or layered with a jacket, and still feel comfy while looking put together.
They’re so versatile, making them a go-to for any season or occasion. If you’re over stiff jeans but still want to look on point, leggings are the move.
Keep it chill, keep it stylish, and let your leggings do the work for you.
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