How to Wear Converse, and How Not To!

23rd June

How to wear Converse

Chuck Taylors by Converse are the classic sneaker for cool, casual style when combined with the right outfit. It isn’t rocket science to rock them. But I do believe there are ways to – and not to! – wear them. Here are 12 DO’s and DON’Ts based on my experiences observing them on the streets.

1) DON’T…

combine Chucks with a totally boring or meh outfit. 

Converse are not your ordinary sneaker. Over the years, they’ve gone from the basketball court to the red carpet. How-ev-er, they don’t perform miracles. 

How not to wear Converse - meh outfit

2) DO…

use brightly-colored Chucks to add a pop of color to your ensemble.

Bright Converse for a pop of color

3) Or DO…

let your outfit do the popping, and let the Chucks stay coolly in the background. 

How to wear Converse - let them fall to the background

Julia’s beautiful sister Lena 🙂

4) DON’T…

set up a competition between your patterned Chucks and other eye-catching pieces. 

A dish with too many spices doesn’t always come out like Chicken Con Mole. Balance is key.

How to not wear Converse

5) DO…

wear your fun, patterned Chucks with a low-key, simpler, or coordinated outfit.

Converse with stars

6) DO…

definitely DO wear brightly-colored Converse with a popping outfit.

Converse automatically make a statement – as retro, artistic, ironic, irreverent, etc. And so, combining colorful Chucks with an equally outfit can be tricky – like wearing stripes with stripes. But, it CAN be done…well. 

How to wear bright colors and Converse

7) DON’T…

wear your Chucks with no laces or loose ones. 

It’s sloppy, especially with worn-looking sneakers. 

Untied Converse

HOWEVER, Converse high tops can sometimes make a girl’s ankles look gangly and disproportionate. In that case, it helps to loosen the laces at the top.  Another way to make your ankles look more proportionate is is to wrap the laces (as seen below).

What to do with high top Converse laces

8) DON’T…

wear Chucks with long, baggy jeans. It brings them dangerously close to the SNEAN (read: sloppy) look.

How to not wear Converse - sneans

Cropped wide-legged jeans, however, can look cool with high tops.

9) DO…

wear them with skinny jeans and pants, especially if you cuff or shorten the hem.

How to wear Converse - skinny jeans

10) DO…

wear them with leggings and athleisure.

How to wear Converse - with leggings with Converse

11) DO…
wear Chucks with flirty, short-hemmed skirts and dresses.

How to wear Converse - short hems

12) and finally, DEFINITELY
wear them with a midi/maxi skirt or dress!

Wondering why I didn’t mention knee-length dresses? They can look frumpy or make legs look stumpy. But that, my friends, is a topic for a whole new post.

How to wear Converse - midi skirt

I hope you’ve enjoyed these looks I spotted in Milan, New York, L.A., Boston, San Francisco, and Seattle, Converse are a classic. They add a serious boost of style to myriad looks – or not. Which is your favorite way to wear Converse?

* This article was updated in May, 2017.

Psst! Have you heard? Converse has come up with the Converse All-Star Modern, which is a totally comfy upgrade! You can find them HERE

xo, janea



13 responses to “How to Wear Converse, and How Not To!”

  1. Beth says:

    Loved your article! I have low converse and just bought hightops! I am a young 60 year young female!

  2. Minka says:

    “1) DON’T…combine Chucks with a totally boring or meh outfit.”

    Umm you totally can. Chucks are THAT iconic for a reason, they’re versatile enough to make a trip to the store look lowkey and make an office outfit pop. Both of the girls in the pics look cute.

    • Janea says:

      Hey, thanks for your comment! This post is a few years old, and I have to admit that my views have changed a bit. I do, however, stand by my personal opinion that if you want to look stylish, Converse don’t save us if we aren’t wearing at least one or two other interesting pieces: maybe a cool scarf/watch/earrings/necklace/handbag. The two women pictured do look cute, but I wouldn’t say that their outfits are particularly stylish. Anyway, it is all a matter of taste, and there you have my personal viewpoint. It isn’t written in stone, and it is constantly changing.

  3. Aissatou says:

    Thank you, as I am new to wearing Chucks, this article really came in handy. I am 61 years old, nearly 62. My first pair of high-top red chucks arrived today. I have seen younger ladies in the red high-top and would drool and then of course forget them. My favorite color is red. Well, in honor of our new Vice President Kamala Harris, decided now was the time. I love them. I have narrow feet so the idea of the hightops is my choice. I already have at least two more pairs waiting. What a way to prepare for being 62!

  4. Michelle Candelaria says:

    How about wearing chucks with Capri pants? Yes or no?

    • Janea says:

      Good question, Michelle. I don’t think that it is the most flattering way to wear either chucks or capris, making the legs look thicker and shorter. To be honest, I feel that capris no longer look that up-to-date. But then it seems like there can be exceptions to everything related to fashion.

  5. Jane says:

    I don’t know about older women and I know this article is a few years old, but for the younger crowd (20-30) baggy jeans+sneakers (converse, nike af1s etc.) are very much in, skinny jeans+sneakers are over. I personally still like to wear skinny jeans sometimes (I’m 27 now), but it’s nice that a looser fit is appreciated.

  6. Jacqueline H says:

    Im 47 and never had a pair of chucks. I love the red high tops with platform bc I’m short. Searched this article to see how to wear them. wouldnt it make me look even shorter to wear these with skinny jeans?

    • Janea says:

      Love those platform chucks! If you get a chance, please let me know if they are comfy. I think that wearing them with skinny jeans won’t necessarily make you look shorter, especially if your top is the same tone as your jeans. That’s a good trick for elongating. Have fun with them! 🙂

  7. Michael says:

    I have seen some teenage girls with wearing their high top converse without socks a lot they just ask me to get a pair, so I do some black high tops, and worn them without socks as they said for a week for some hot days. as I had noticed that they made my feet sweaty and stinky within my converse having to throw them out sadly gone, I watched them being back loaded into the garbage truck crushed as they smelled so bad, like it made me think about of those girls ones on them like they had theirs for 2 years like this and I told them about it now they have found my way is better I love fashion. because by wearing they give blasters and smellness they don`t last long then. I have since then now have got new ones with socks and best worn with shorts or jeanes sometime trackis.


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