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No shoes are more iconic then Converse. Initially considered as skater shoes, these sneakers have now conquered a place in the Olympus of fashion and we all have at least one pair of Converse in our wardrobe. If you are in love with their style, why don’t you experiment with new outfits to make them shine?

Here you will find plenty of inspiration to style your high top converse.


What Can I Wear High Top Converse With?

High top Converse are a timeless classic, which can suit any aesthetic. For example, you can keep your outfit simple and rock your shoes with a casual denim or even a pair of comfy chinos. On the other hand, you can make the look more dynamic with some cuffed pants or pleated shirt. Of course, you can play with different lengths when it comes to shoes and pants.

Do You Tuck Jeans into High Top Converse?

Streetwear fashion has heavily influenced contemporary looks, making it now acceptable if not even fashionable to tuck jeans into high top Converse (or any other pair of sneakers, if you prefer). If you want to try this look, you must make sure that your jeans fit neatly inside your shoes, without leaving your skin exposed. For this reason, slim-fitting jeans usually are the best choice, provided that they have the proper length.

Do You Wear Socks With High Top Converse?

Socks can be a nice piece of accessory to make your look unique and more colourful. However, they might be just barely visible if you are wearing high top Converse. For this reason, if you still want to make them part of your outfit, you should play with contrasting colours. For example, wear some neon socks underneath your black high top sneakers, and make sure your skirt or pants have the perfect length to make it show.

Can You Wear Converse With Leggings?

One of the best things about Converse is that they just look iconic with every outfit and other pieces of clothing, including leggings. Usually, leggings are more recommended with Chuck Taylors, which hit your ankle differently. However, you can still rock some high top Converse with a cool pair of leggings if you match the proper colours and styles. Try this look with a sweater vest to get the best result.

How to Wear Hi-Top Converse Shoes

Hi-top Converse shoes are not just for fashion – they’re for comfort as well. Since it provides ankle protection, you don’t have to worry about sprains and injuries – even if you’re only using your Chuck Taylors for fashion purposes. They also provide better stability, which is why hi-top shoes are great for creating these chic outfits: 

Dress it Best

Dresses and sneakers go unbelievably well together. So if you’re tired of wearing your frocks with heels or sandals, then it’s time to pair them with your hi-top Converse shoes. 

Like the model, keeping it simple is the way to go. You can imitate her sophisticated style by wearing a simple long dress and a well-fitted blazer. Throw on a few accessories – just like her layered necklaces – for an outfit that’s glamorous enough for work (or some other place). 

Summer Sunshine

Speaking of dresses, Alexa Chung’s summery look is another one you should try with your hi-top Chuck Taylors. 

To get the model’s fresh look, pair your airy floral summer dress with your black Chucks – or any other color you have. You should also keep a jacket or cardigan handy by wrapping the sleeves around your waist (or neck). 

Styling tip: Don’t forget to accessorize your summer outfit with a cute pair of earrings or a dainty necklace. 

Fun Yet Formal

While Chuck Taylors were developed for athletic purposes, you can wear them with your fancier outfits too. Just take a look at this model, who looks like she’s ready to go to work with her hi-top Converse shoes.

To get her formal look, assemble a get-up that you often take the work. A plain tee or a white button-down top, a sleek blazer, and some well-tailored trousers are great – though you can explore other fashion possibilities as well! 

Leather is Better

Although leather is more suitable for cold weather, this model shows that you can sport it during the hotter seasons as well.

To pull off a sweat-free outfit, make sure to wear lighter garments such as a plain shirt and leather shorts. Complete the look with a leather jacket, which sleeves you should pull up to your shoulders.

Styling tip: You can wear the jacket around your waist in case the temps get unbearably hot! 

Sporty Spice

Whether you’re athletic or not, a sporty fashion style is something you ought to try with your hi-top Converse shoes. And just like the model, you need not go far to piece the complete look.

For one, you can borrow your boyfriend or brother’s jersey and wear it with your denim shorts. It need not be a basketball jersey though, as you can wear his baseball or soccer uniform as well. Just remember to tuck it in so you could flaunt your figure underneath the loose fabric. 

Red on Red

Apart from the black or white hi-top Chuck Taylors, a red pair has become one of the more popular Converse shades to date. And for people who love to do a monotonous look, it’s the go-to color for a more striking outfit. 

Like the model, pairing your red Converse shoes with a red frock is a thing of relative ease. If you want, you can take everything a notch higher by swapping your dress with an all-red pantsuit! 

Pantsuit Up

Speaking of pantsuits, this ensemble is another thing you could wear to the office with your Chucks. But instead of the usual black or navy suit styles, go to the bright side and wear a unique (if not peculiar) color. 

As seen on the model, pink is a lovely shade to try especially if you want to truly stand out. And instead of wearing the traditional button-down, you can achieve a more casual look with a plain top. White is best but it wouldn’t hurt to pick another shade of pink as well! 

Pretty in Pink

Although black or white hi-tops are classic Converse choices, you can go beyond this with colorful footwear. Like the model, you could go for a pink pair of Chuck Taylors. 

To cop her casual look, wear a vest on top of your sweater (or just have the latter alone). Pair these with a flirty skirt – or a denim one if you like. With this style, you’re sure to enjoy a comfy girly ensemble. 

Flower Power

There are so many ways to wear your Pink Converse shoes. If you want to unleash your fun and flirty side, then make sure to follow this model’s lovely spring (or summer) outfit. 

Apart from being stylish, this get-up is very easy to recreate. After all, all you need are 2 things – a graphic tee (or a plain one) and a floral skirt. Like the model, you can achieve a pink-centric look by taking a pink bag along with you.  

How to Wear Low-Top Converse Shoes

Compared to hi-top Chucks, low-top pairs provide freer ankle movement. This is good for sudden movements – at least for athletes. Even if you’re not a sportsman, Converse shoes will work to your fashion advantage as long as you follow these styling tips. 

Black is Back

An all-black outfit is not necessarily boring. With your low-top black Chuck Taylors, you can create an impeccable outfit like this one. 

The key to getting the model’s elegant look is to use black pieces with different textures. For example, you can wear a silk cami with a wool blazer and faux leather pants. For a true monotone look, make sure to have everything in black – and that means your sunglasses, belt, and handbag. 

Styling tip: You can break the monotony (even for a bit) by wearing an all-black attire with your white Converse shoes. 

White is Right

The color white is a pristine color to try for your spring or summer outfits. When worn with similarly white Chuck Taylors, you can achieve a look that’s fresh and comfy.

To cop such a style, make sure to refer to actress Dianna Agron of the Glee fame. The actress keeps everything clean and simple with her puff-sleeve dress, white bag, and of course, white Chuck Taylors. If you want to go completely white, you can wear your white-rimmed sunglasses as well! 

Borrow it From the Boys

An androgynous look will not only make you look fashionable – it can make you feel comfy as well! That’s because this outfit usually makes use of loose items that give you a lot of room to breathe.

Add to that, an androgynous outfit is one of the best get-ups to pair with your white Chuck Taylors as well. As seen on this chic model, all you need to do is borrow your beau’s clothes – and that includes his trench coat, button-down top, and pinstripe trousers. 

Lace Craze

A total opposite of the androgynous style, the lace craze – as the name suggests – is all about items made with delicate fabrics. And while it’s very romantic, you can add some edge to it with the use of your hi-top Converse shoes. 

Like the model, it’s all about sporting lacy pieces similar to her top and skirt. Top them off with more structured pieces, such as a hat and geometric bag. And for full comfort, don’t forget to wear plush socks with your favorite Converse kicks!

Cute in Coordinates

If you like all things matchy-matchy, then wearing coordinates is the way to go. And even if they’re ultra-luxe – just like what the model wears – they’ll definitely look good with your white Chuck Taylors.

In this picture, the model combines the best of both worlds – a sophisticated coordinate set and a designer bag to go with her low-key Converse shoes. And with the latter in tow, you won’t have to worry about tripping on wet concrete. 

Enviably Elegant

Luxe evening dresses don’t always have to be worn with sandals or heels. As this model shows, it’s good enough to be flaunted with a pair of white low-top Chuck Taylors. 

If you’re wearing a pretty elaborate dress, know that you don’t have to go ga-ga over the styling. Like the model, you don’t need much froufrou. As long as you have spunk and attitude, you can pull this outfit off like a fashion pro. 

Short and Sexy

Speaking of dresses, your short cocktail dress is another garment you should wear together with your low-top Chuck Taylors. As seen on the model, this combination is posh enough for the glitziest of red carpets!

Completing this look is fuss-free too, as you don’t have to worry about your dress clashing with your shoes. You can pick any style and color without any problem. And of course, don’t forget to keep your accessories at a bare minimum. 

Button-Down Beauty 

Just like a pair of low-top Chuck Taylors, a button-down top is a classic piece any woman must have. That said, these 2 trademark pieces are sure to work well together.

As seen on the model, a pair of Converse shoes (especially if it’s in bright red) can add some pizzazz to your simple button-down outfit. Like her, you can inject a bit of ruggedness by wearing your crisp top with a pair of tattered/frayed jeans. 

Print Galore

Are you adventurous enough to mix various prints? That’s a good thing because you can easily pull this trend off with the help of your white, low-top Chucks. 

To get this model’s look, wear a striped shirt with a solid-colored skirt (or shorts). Cover them up with a Leopard print jacket or trench coat – or one with a geometric style. With your Chuck’s simple style, it won’t get in the way of your print-on-print outfit. 


Like her mother Cindy Crawford, Kaia Gerber has shown that she too is a fashion icon to be reckoned with. An enviable fashion chameleon, she can pair uniquely different items with relative ease.

Just take a look at this outfit, which features a ‘formal’ printed top and casual jogger pants. Together with her hi-top shoes, Kaia has created a comfy yet fashionable black and white outfit. 

Outstanding Overalls

Overalls are not just for kids. A popular item amongst celebrities and fashion bloggers alike, overalls are trendy alternatives for the usual pants and trousers. They can be worn with most types of tops, with the model’s oversized sweater being a good example. 

Like her, you can style your jumper to show your hi-top Converse shoes. All you need to do is fold or roll the hems a few inches above your Chucks. 

Punk Rock Chic

Creating an edgy look is very easy with your low-top Converse shoes. Case in point: this stylish model, who looks the part with her punk rock outfit.

To recreate her get-up, all you need are 2 basic things: an oversized graphic shirt and ripped denim shorts. For some fashion flair (and warmth too), make sure to wear tights and knee-high socks as well. Put on a beanie and sunglasses and your look is complete!

Whether you have low-top Chucks – or a hi-top one – you definitely can wear any of them with your favourite outfits. And as long as you follow the tips above, you’re sure to create a look that’s worthy of Pinterest or Instagram. 

Other Articles That May Also Interest You:

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14 High-Fashion Tips on How to Style Overalls Like a Pro

How to Style a Sweater Vest (Women’s Edition) – Outfit Ideas for all Seasons

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About The Author

May is totally crazy about the 80s and everything the decade inspired! Having grown up in a household that was totally taken over by 80s music and fashion its only natural that May lives and breathes the 80s!

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