How to (and How Not To) Wear Converse

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?

XO, Janea

* This article was updated in May of 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

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