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*2023*High Top Converse With Dress & look forgiving! 33 looks!

*2023*High Top Converse With Dress & look forgiving! 33 looks!

Wondering how to wear high-top Converse with the dress?

Well, you’ve come to the right place!

First thing first, shall we all admit that high-top sneakers are not that effortless to style with?

As a petite girl who obsessed with high-top Converse since she was 11 years old, the struggle is real.

high converse outfit
Source: Pinterest

But over all these years, I tried out all kinds of combos and realized the truth – The high-top Converse DOES work great with some types of dresses!

And when I say work great, I mean looking 10/10.

So here you go ladies, I’m here to share 33 outfit combos to wear high-top Converse with the dress & pants without looking short.


1. High Top Converse With Overall Dress

Whether it’s a casual date night or a weekend outing plan with friends, you just can’t go wrong by wearing overalls with high-top Converse.

High Top Converse With Overall Dress

I know, some of the photos above are overall pants, but hey – you get my point.

A carefree overall always works wonders with casual high-top Converse!

The thing I love about these cute overalls is their ease of styling.

Regardless of the season, there will always be a way to pull off an effortless overall dress look.

From summer denim to winter corduroy overall, they are just lovely.

Of course, you can also transform your summery overall into a more warm fall outfit by changing from a T-shirt to a high top, and your work is done!


Adding a cute wide pearl headband can be a game-changer to this entire look. It just makes people think you’ve given extra thought.

Is that just me but the black and red color combo is always HOT.

red high converse top outfit ideas
Source: Fashionmcgee

By matching the top and shoes in the same hue, this is how you enjoy the leg elongating effect even in flat shoes!

2. Patterened mini dress with Converse

So ladies, If you have a special something in your heart for plaids, then the high-top Converse is a must-have in your shoe collection.

mini dress with Converse
Source: 1, 2, 3

Plaids are an effortless fashion. Don’t believe me? Have a look yourself at how gorgeous these women in plaids look.

All you have to do is put on your favorite plaid dress with a pair of high-top Converse and minimal accessories.

you are all set to turn some heads with your exclusive taste in fashion.

patterned dress and converse
Source: 1,2


Some girls may think patterns like plaids can make them look bigger.

To balance things up, opt for the one with smaller plaids or with color combos that are less contrasting definitely helps.

Also, a big V-neck also helps shed down the heaviness of the prints.

3. High Top Converse x shirt dress

Looking for some easy breezy streetwear look with your high-top converse?

High Top Converse and shirt dress
Source: 1, 2

Why look somewhere else, when you have the oh-so-sassy oversized button-down shirt dresses in your wardrobe?

As an oversized shirt can be quite flirty, team it with a high-top Converse just balance things out perfectly as an in-style streetwear look.

To add a dose of artsy vibes, show your knee socks with your white high-top Converse can be a cool look.

Remember, looking stylish is all in detail.

self tie wrap shirt dress white converse
Source: Anindigoday

This outfit is a 10/10 and yes that pair of sunnies elevate the look even more!


Keep your collar button open and fold your sleeve to your elbow to impart a carefree vibe into your button-down dress.

4. Stay Feminine With Floral Prints

Thought you could never pull off a classy feminine look with your high-top Converse?

Well, think again!

Floral Prints and high top converse
Source: 1, 2, 3

Guess what, these floral prints with Converse are a booming fashion these days.

And if you haven’t tried them yet, girl you are missing out.

So ladies, embrace your feminity in style this summer with these vibrant floral dresses and look well thought out whilst looking casual and practical.

floral dress high top converse
Source: Pinterest


While choosing floral prints, pay attention to the pattern.

Try to go with small flowers as a big floral print dress can make you look more wide and bulky.

Another tip, the high-top Converse doesn’t work great with the long bodycon dress – just don’t do it.

5. Casual Winter look with High Top Converse

Winters are all about layering dresses with aesthetic jackets.

So, if you are unsure how to wear high-top Converse with dresses in winter, you are at the right place!

Casual Winter High Top Converse
Source: 1, 2, 3

All you have to do is throw on a jacket or coat to your regular winter dress to complement your high-top Converse and here you go; all set to slay your winter styling game like a fashionista!

To look more effortless, drape your denim jacket over the shoulder just boost the boss babe vibes tenfolds.



Try to choose shorter-length or crop jackets to wear with your dress.

They are perfect when it comes to drawing your eyes upward and making you look taller within Converse.

6. High top converse with faux leather leggings

When the days are cold out, teaming the leggings with Converse is actually a super cool look.

converse with leggings
Source: Pinterest

A flamboyant yellow sweater, leather black leggings, and high-platform Converse?

It is screaming the effortlessly cool girl vibes.

winter high converse outfit
Source: Girlsharetips

Another big plus?

When you wear the same hue, it just looks so leg-lengthening without even trying.

winter converse outfit with trench coat
Follow @beth_bartram on LTK

When in doubt, get creative and mix the leisure wear with a trench coat.

To stay put together, again – matching the cap and shoes in the same shade greatly helps!

7. Baddie Style x High Top Converse

Baddie fashion is all the rage these days.

So girls, if you also want to jump on the bandwagon here the easiest way, you can do so.

T shirt dress and High Top Converse
Source: 1, 2, 3

Wear your oversized t-shirt dress with some statement neckpiece and a pair of high-top Converse and see the magic happen.

However, do not forget to wear mid-calf trainer socks matching your Converse shoes for an ultimate baddie vibe.

BADDIE outfit sneaker
Source: Pinterest

Is that just me or her smile is so contagious?

8. Go Monochrome For A High Fashion Vibe

When in doubt, go monochrome, the only mantra to pull off an aesthetic high-fashion look.

Monochrome high top converse women
Source: 1, 2, 3

So ladies, if you are looking to transform your basic high-top Converse outfit into an expensive business, look no further!

Whether you opt for a backless mini dress, a leather jacket outfit, or a sweater vest look, going black and white can make any outfit a bougie fashion, effortlessly.

white monotone outfit with converse
Follow Laura.Byrnes on LTK

This is definitely high fashion vibes.


For the petite girls, definitely choose the converse with an elevated outsole like this one. Such a confidence booster.

9. Long dress x high top Converse Look

If there is one dress you can never go wrong with, while styling with your high-top Converse, it will definitely be a maxi dress.

The Classic Maxi Dress With Converse Look
Source: 1, 2, 3

No matter what age you are or what are your style preferences, a maxi dress and the high-top Converse is an outfit combo that no woman can say no to.

whether you opt for floral prints, animal prints, or solid maxi dresses with your Converse, it all comes down to the choice of your accessories and how you carry them.

So ladies wear them with confidence and a bright smile to sweep them off their feet with your personality and taste in fashion.


So there you go ladies – the 33 outfit combos to wear high-top Converse with the dress without looking short.

What are your thoughts on that? I hope these looks get you inspired and it’s time to go try out a new style and feel THE BEST.

If you are looking for more outfit tips? Check out my popular reads below, see you there loves!

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