Tops To Wear With Leggings: DO’s & DON’Ts

Hi there, nice to meet you. I’m Savina, a minimalist fashion blogger, and today’s 101 is all about tops to wear with leggings.

May I ask you something? Are you a leggings lover? If yes, you know I’m talking about one of the comfiest (if not THE comfiest) pieces to wear. They are the perfect pair when looking for what to wear with tops. Soon you will want to have it in tons of different colors and never (ever) switch back to regular pants. 

Although the statement above is more than proven valid, even the best leggings are not easy to style. Especially if you don’t know what to style them with.

Looking at the big picture, it’s important to keep balance in terms of proportion. That’s why I’ve stepped aside from fashion trends and explored some different ways to do so.

Therefore, feel free to copy-paste the best choices (all below!) for upcoming business meetings or simply for those moments when you are pinning stylish legging outfits on your Pinterest board.

Get the white sneakers and oversized sweatshirt ready, and let’s dive deep. Bonus points if they are vegan!

Knowing what tops to wear with leggings is one thing. Being able to match and style them is another. After reading this, you will learn both.

TOPS TO WEAR WITH LEGGINGS: DO’S & DON’TS

DO WEAR:

Long oversized sweaters  

When it comes to styling leggings, the more oversized the top, the better. Playing with length and thicker fabric might get confusing, so let me sort it out for ya – it’s best to get a dark-colored pair of leggings and opt for a neutral oversized sweater (white, beige, brown, or gray). A long cardigan will work too.

Don’t be afraid to add embellished sunglasses and some chunky ankle boots to keep the proportions. Olivia Palermo would approve.

P.S. Here are more cozy sweaters to wear with leggings to get inspired for the winter season.

Oversized blazers  

Oversized blazers are a wardrobe staple to wear with not only leggings but with literally anything. Let’s not get distracted, though. In this case, I’d style them with either classy ankle Chelsea boots or knee-high boots in fall/winter to balance the top out. This way we have a bit of bulk on the top, skinny legs in the middle, and a bit of chunkiness at the bottom.

When talking about work outfits, I’d replace the Chelsea boots with ballet flats. During the summer, chunky sandals or chunky sneakers would work great.

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Long coats 

I don’t know why, but many people are still going either leisure or formal. Now let’s try the best of both worlds. These are the kind of tops to wear with leggings in winter. Long coats in solid colors are a great way to elevate your casual look and make it a sophisticated one in a matter of milliseconds when we are talking about black leggings. Finish with black boots to elongate the silhouette.

Boxy jackets  

Short boxy jackets are not everyone’s cup of tea, especially if you’re someone who’s conscious about their thigh area. *Skip to the next point, if so.* However, they look amazing paired with a tall boot and a small shoulder bag. All you need to adore this #OOTD is classic black leggings (fitting every body type!) and a graphic t-shirt to make everything less prep and more ‘I know what I’m doing’. If you’re into that, of course.

Trench coats  

I may have said it more than one or two times, but what are you doing with your life if you don’t own a classy, timeless trench coat? Defining everyday wear, trench coats will look ah-mazing with your favorite leggings and chunky sneakers.

The right accessories? Your choice. Golden bracelets, hoop earrings, funky rings, it’s all good. A baseball cap? Sure, go for it. Mixing female and male elements in an outfit is a great way to spice up your style and make it more unique. 

Hoodies  

I’ve never been good at Math, but hoodies + long coats + boots + high-waisted leggings = a perfect match. Of course, I would pick something that doesn’t have too many prints or signs all over it, but you can make it the focal point of your outfit. Switch the hoodie with a stylish top, and you’re ready for a date night out. Versatility is what we are all here for.

Overshirts  

Is it a shirt? Is it a jacket? Oh, it’s both. So let’s put it down once again. The chunkiness of the overshirt counteracts the skinniness of the leggings and balances the silhouette out. In other words, it’s necessary to pair that lovely oversized shirt with tight leggings, so you don’t look like Santa’s sack.

Check This Out: ALL THE ESSENTIAL WINTER STAPLES YOUR WARDROBE NEEDS

Oversized shirts  

Moving from overshirts to oversized shirts, I’m simply describing another easy way to turn the I-have-nothing-to-wear crisis into a fabulous office makeover. This makes them the best tops to wear with leggings to work. Once cooler weather takes over, I’d add a long coat, an oversized sweater on top, and ankle boots at the bottom.

For summer, chunky sandals are a great option – avoid high-top sneakers since they usually cut the leg off. Get yourself a big tote bag to balance the proportions out, and shop in style. It’s a good idea to have a few cute long shirts to wear with leggings all year round.

Sweater vests  

I know that sweater vests are pretty particular, but if you’ve tracked down most of this year’s street style findings, the combination with faux leather leggings shouldn’t come as a surprise. The game of textures is really charming. Plus, you don’t need a lot more than a pair of boots before going out. In case you’re not convinced this is the right match for you, try a neutral shade for the vest and add a pop of color over time.

Sports bras

Think crop top, but better. Sports bras go hand in hand with many things and, yes, leggings are one of them. Ideally a matching set (leggings + sports bra), so you really look put together. They are great tops to wear with leggings in summer. 

My advice would be to style with oversized shirts and chunky trainers. Quickly switch up this look from your workout outfit if you have dressy tops to wear with leggings. Or just throw on a denim jacket if you have a brunch meeting that you don’t want to be late for… again.

AVOID WEARING:

Tight tops (tight shirts, t-shirts, or blouses)

You may have come across the word ‘oversize’ a few times, but when it comes to pairing leggings, volume is key. Otherwise, your chances of looking outdated and a bit boring will go way up. I’m not saying you should throw away all your more fitted types of tops, just implement them in other outfit ideas. 

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Tight turtlenecks and sweaters

As we said, with tight tops, they are a no-go with leggings. Tight turtlenecks can work great with looser bottoms like wide-leg pants or balloon jeans, but not here. Let’s keep it loose with leggings, shall we?

Tight jackets

Tight jackets are another big NO when we’re talking about your favorite pair of black leggings. Instead, go for a slightly oversized faux leather jacket or a puffer to balance the look out. You can see the pattern here now, right?

Short and cropped tops (except sports bras)

Not just for winter, but in general, I’d avoid short tops (apart from sports bras) in a legging outfit combination. There are definitely some people who can pull this look off, and if you’re one of them and feel comfortable, go for it! I personally avoid it as it’s just a bit too basic and simple.

Instead, I’d style my black or even white leggings with a classy tee and padded shoulder blazer to add some volume at the top, which will even out the lookout and make it more modern and chic.

It’s safe to say that it doesn’t matter if you want a classic look, a laid-back look, a cute look, a chic look, or maybe all at once, this blog post has got it covered. And whether you are into workout leggings, black leather leggings, or legging outfits in general, you’re welcome.

Fashion For Thought

In wrapping up today’s leggings lowdown, remember that leggings are a versatile base for countless looks. Ditch those skinny jeans for a bit, and let’s embrace the comfort of a leggings outfit.

For a look that’s perfect all year round, pair with a long shirt or a longer top. These are your go-to for that effortlessly chic vibe. In the search for the best shirts to go with leggings, don’t shy away from tunic tops, they’re a good choice when seeking that perfect length.

During those colder months, opt for a long sweater or an oversized cardigan for an extra layer of warmth without sacrificing style. And yes, for casual occasions, a flannel shirt or a chambray shirt over leggings creates a cute outfit that screams cozy yet stylish.

Want something for a dressier look? A white top, especially a long tunic or a button-down shirt, is the perfect choice. Add high heels for a dash of sophistication, and you’re good to go. On more laid-back days, swap those heels for tall boots or an oversized t-shirt for the ultimate casual wear.

Layering? Yes, please! For a layered look, a tank top under an open button-up shirt or a denim shirt works wonders with leggings. And let’s not forget the different ways to incorporate different styles—plaid shirts for that touch of grunge or a graphic tee for an edgier feel.

Short dress on hand but not ready for the bare leg? No problem. Slip on those leggings for a modern twist on a classic short dress. It’s about playing with proportions and creating balance.

And there you have it—the leggings manifesto. Whether it’s casual leggings for athleisure wear or a black outfit for a night out, these wardrobe staples can be styled in different ways.

From bright colors to shorter tops (save those for your blue jeans) to the perfect combo with a long coat, your leggings can do it all.

So next time you’re puzzling over how to wear leggings, just remember: it’s all about mixing different shirts, lengths, and styles to find your unique look. Go on, create good outfits that celebrate your style—your leggings are ready to play!

With all your comfortable outfit desires sorted, what should we talk about next? Let me know on Instagram @savinaofficial!

This post was all about tops to wear with leggings. 

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