Dianne If you love looking stylish wearing leggings as much as I do, you’re going to enjoy this post and video because I share 10 casual chic outfits with leggings that you can wear to look and feel stylish every day.
Created for women over 50, I am sharing these outfits because we all need outfit inspiration once in a while that makes us feel confident and beautiful.
This post is all about stylish outfits with leggings to help you look and feel your best every day.
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Cute Outfits with Leggings
Our lives post-2020 are more casual than I can ever remember. To be honest, I don’t mind it at all. Many of us have taken this opportunity to decompress after being wound up tight. We have spent more time with immediate family, getting to know ourselves better, experimenting with recipes, eating together more, and doing things we rarely had time for in the past.
Best of all, we spend more time in our favorite comfortable clothes, which for most of us women, include leggings! If you’re anything like me, leggings are one of your favorite go-to’s and have become a wardrobe staple. While they are not new to our closets, they have changed and evolved a lot over the years. They started off as flares then became skinny, and now they are coming back around again. We wear leggings for yoga, leggings for running and leggings for pure fashion sake. This post is all about fashionable outfits with leggings that you can turn to for inspiration every day.
Best Affordable Legging Brands
There are tons of leggings brands and price points to choose from, but in my experience the cliche “you get what you pay for” is not true when buying quality leggings. I have found some really great leggings brands that rival the big names. Lululemon’s leggings are where it all started for me, and while I love them, I have also found a few other very similar options at a fraction of the price.
If you’re looking for some affordable, high-quality leggings, I have a couple of recommendations I found on Amazon. Trust me, I must have ordered twenty pairs of leggings before I narrowed it down and found the best. Here they are and I think you’re going to love them:
Sport Leggings You Need In Your Life
Hey Nuts brand offers very high-end sport leggings that fit like a dream. If you like the thicker type leggings that offer some compression and are in the market for black leggings, burgundy leggings, olive leggings, graphite leggings and several other colors, check out this brand! You need these leggings in your life!
Lounge Leggings for Ultimate Relaxation
IUGA brand offers high-quality leggings that feel like a second skin and are ideal for lounging. They have the perfect dark brown leggings, plus lots of other colors too. Great if you’re looking for a perfect pair of leggings for relaxing.
Casual Chic Outfits for Everyday
1. Leggings Outfits for Work
So you don’t want to part with your leggings when you head into the office? I have the perfect outfit option for you. Pair your basic black leggings with a crisp pink button-up shirt, a long grey cardigan sweater and a pair of black knee high pointed toe boots for a very polished, professional look. This pink button-up shirt is the perfect length to cover the top of the leggings and disguise them to look more like trousers than leggings.
Pearl Necklace, Pearl Stud Earrings
2. Sweater and Leggings Outfit
Stylish and sophisticated, this outfit with leggings is perfect for a casual fall or winter day when it’s cold and blustery outside.
The camel crew neck sweater and black leggings look chic with the long black and white striped shirt, peeking out from the bottom. By adding a side tuck, this blouse looks elevated and modern. The pearl necklace and pearl stud earrings add the perfect amount of interest and elegance, while the cognac riding boots finish this outfit masterfully.
This outfit is classy and comfortable and will keep you warm and cozy all day.
3. Olive a Comfy, Cozy Leggings Outfit
Get it…olive (I love)? Okay, kinda cheesy. Anyway, I love this comfortable, cozy outfit. This olive, navy and gray sweater outfit with leggings is charming and cozy. Perfect for a day at home, but also cute, if you dash out to the store or the library and you run into a neighbor or old friend.
The white henley with crochet detail is the perfect canvas has great feminine texture, with the pearl necklace and earrings perfectly complementing the girly vibes of this outfit. The interesting texture of this long hooded cardigan pairs perfectly with these beautiful olive leggings and brown over the knee boots.
Charming and cozy for sure!
4. Blue Jean Jacket with Leggings Outfit
Casual and chic, this jean jacket outfit with brown leggings is stylish, simple and modern.
When paired with this feminine white henley with crochet detail on the sleeves and yoke, dark brown leggings and tan suede ankle cowboy boots, the look is perfect for an afternoon of shopping or a day at the zoo.
This easy to wear leggings outfit is charming and fun.
5. Burgundy Leggings Outfit
Cute and very comfortable, this relaxed outfit with leggings is perfect for a day of lounging or joining friends at the local pub for pizza and a football game.
These burgundy leggings and long cream hooded cardigan sweater pair well with this chambray shirt and brown over the knee boots to create an effortlessly chic casual weekend look for most anything you might have planned.
Polished, yet casual, you are ready for the day.
Get This Look: Long Cream Sweater (similar), Chambray Shirt (similar), Pearl Necklace, Pearl Stud Earrings, Hey Nuts Burgundy Leggings, Brown Over the Knee Boots, Black Camo Slide On Sneakers (similar)
6. Flannel & Leather Leggings Outfit
Cool girl casual, you need this black and white plaid flannel outfit with leggings in your clothing repertoire. Very modern and youthful, you’ll feel ten years younger wearing this outfit.
This black and white plaid flannel and cream puffer vest looks amazing, with these black faux leather leggings and tan suede ankle cowboy boots.
Such a cute, hip, girl-next-door kind of look.
Get This Look: Cream Puffer Vest, Pearl Necklace, Pearl Stud Earrings, Black and White Plaid Flannel (similar), Black Faux Leather Leggings, Ankle Cowboy Boots (similar), Black Camo Slide On Sneakers (similar)
7. Olive Cargo Vest & Leather Leggings Outfit
Such a charming outfit and not a look you see every day. This rustic olive cargo vest is a perfect juxtaposition to this feminine white henley with crochet detail in the sleeves.
The cognac riding boots with the black faux leather leggings are the ideal pairing to create an effortlessly chic outfit.
Another stylish casual outfit for when you’re not sure what to wear.
8. Utility Jacket & Cream Leather Leggings
Don’t you love the versatility of a neutral tan or olive utility jacket? Besides my leggings, I frequently reach for a utility jacket to polish off a casual outfit before I head out the door.
Here’s another perfect opportunity to pull out an old stylish favorite. Styling your utility jacket with this pink button-up shirt, black faux leather leggings and brown cowboy boots with pink and cream accents. The ensemble is something a little different when you want to switch-it-up.
Pulled together and stylish, this is curated to look chic while remaining perfectly comfortable.
9. Elegant Outfit with Leggings
Super cozy and very elegant, this black and white outfit with leggings is polished and classy.
Pairing this long black cashmere turtleneck with these stylish cream leather leggings and pointed toe leopard print flats screams sophistication, yet it is still very comfortable and wearable.
Perfect for dinner out, and a fall or winter birthday party.
Get This Look: Blue Jean Jacket, Black Cashmere Tunic Turtleneck Sweater, Long Gold Pendant Necklace (inspired), Cream Leather Leggings (similar), Rothy’s Wild Cat Pointed Toe Flats
10. Black, Tan & Cream Leather Leggings Outfit
Edgy and chic, this chic casual black and tan leggings outfit will keep you warm and comfortable in perfect style.
This khaki utility jacket paired with this black button-up shirt, cream leather leggings and tan suede ankle cowboy boots looks modern and fresh.
Super stylish. You will look like a fashion icon when you walk into the room with this outfit.
Get This Look: Khaki Utility Jacket, Black Button-Up Shirt (similar), Pearl Necklace, Pearl Stud Earrings, Cream Leather Leggings (similar), Ankle Cowboy Boots (similar), Black Camo Slide On Sneakers (similar)
For more outfit inspiration, check these out:
- How to Look Good in Jeans and a TShirt over 50
- How to Wear a Scarf | Effortlessly Chic Casual Outfits
- 10 Elegant Outfits with Blazers and Jeans
