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May the Ray

A lifestyle blog for the dream chasers

Style · September 11, 2026

10 Leggings Outfits to Keep You Warm and Stylish This Winter

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I don’t know about you, but I absolutely love the comfort and convenience of leggings. You might be surprised by this, but you can totally wear leggings in the winter if you make the right choices. These winter leggings outfits are proof that you can stay warm and cozy without giving up on looking cute.

There are some amazing fleece lined leggings out there that offer a lot of protection against the cold and honestly lots of companies have really made the effort to develop heat related advancements to clothing so what I’m saying is that you can enjoy a good pair of leggings all winter long!

Winter Legging Outfits I’m Obsessed With

1. With a Fleece Jacket & Hoodie

girl wearing white fleece jacket, hoodie and leggings
SHOP THE LOOK

There’s something really simple yet cool about a fleece jacket paired with leggings. It’s the type of cool-looking jacket you can layer over a look like this with a hoodie, leggings and sneakers. Simple, cozy and still cute!

2. With a Long Black Coat

a girl wearing a classic black longline coat paired with casual gray sneakers and a canvas tote bag.
SHOP THE LOOK

Who said leggings outfits have to be simple? You can style a pair of leggings with a chic long black coat, and you could totally go for an all-black look. I’m obsessed with the pairing of the black coat with the black hoodie and leggings. It’s giving effortless and put-together without trying too hard.

3. With a Quilted Puffer Jacket

girl wearing a white quilted puffer jacket, sweater, leggings and uggs
SHOP THE LOOK

Sometimes a light puffer jacket is all you need. I love the styling of this look because it’s casual but still warm and fun. By pairing the lightweight quilted puffer jacket with the sweater and Uggs, you have a cute, warm and layered look.

4. With a Leather Jacket and Hoodie

girl wearing a leather jacket, leggings and boots in front of a mirror
SHOP THE LOOK

Want a look with a bit of edge? Then you’ll be obsessed with this look. You can pair a faux leather jacket with a hoodie for a fun and edgy leggings look. I love how the leather jacket instantly makes the outfit feel a little cooler.

5. With a Puffer Jacket

girl wearing puffer jacket and leggings and boots
SHOP THE LOOK

I don’t know about you, but I love a good puffer jacket. If you need a cute and simple winter outfit, throw on a puffer jacket with the leggings and some chunky Chelsea boots to tie it all together. It’s one of those outfits that looks like you put in way more effort than you actually did!

6. With an Oversized Knit Sweater

girl wearing an oversized sweater paired with leggings and casual sneakers
SHOP THE LOOK

This is another look I would describe as simple yet stylish. I can’t get over the pairing of the simple sweater with the leggings, the socks and the simple sneakers. Sometimes you really don’t need to do too much to make an outfit look good.

7. With a Coat and Cardigan Combo

girl wearing brown coat, cardigan and leggings outfit
SHOP THE LOOK

Love, love, love styling like this. It screams casual but is still stylish and put together with the layering of the leggings, the cardigan and the long coat. This is definitely the kind of outfit I would reach for on a cold day when I want to be comfortable but still look cute.

8. With a Coat and Sweater

girl wearing a blazer, a sweater and a white shirt underneath with leggings
SHOP THE LOOK

The academia aesthetic is what this look reminds me of. It’s put together in a way that is preppy and cool, with the blazer paired with the quarter-zip sweater and the oversized shirt layered underneath. I love how the leggings keep the whole look casual while still giving it that polished feel.

9. With a Puffer Vest and Hoodie

girl wearing a puffer vest with a hoodie and leggings
SHOP THE LOOK

I would describe this as another cute puffer jacket and leggings outfit. Layering a puffer vest with a hoodie is surprisingly cool with leggings and sneakers. It’s such an easy combination, but somehow it still looks really put together.

10. With a Long Brown Coat

a girl wearing a brown suede trench coat over a matching outfit.
SHOP THE LOOK

I love an all-brown look. This is a great way to style the color brown, and I’m absolutely obsessed with the pairing of the brown top with the brown leggings and the brown coat. There’s something about wearing different shades of the same color that makes an outfit look so effortlessly chic.

Posted By: ngozamay · In: Style

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About Me

May is a twenty-something year old lifestyle blogger who likes travel, food and spends inordinate amounts of time reading. Her life motto is "try everything at least once!" Read More…

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Hi there! I'm May and welcome to May the Ray, a young adult lifestyle blog where I share tips about lifestyle, food, fashion (+ so much more!), and where I try to inspire people to live life to the fullest!

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