Chuck Taylor Shoes: How to Style

Chuck Taylor shoes by Converse are functional for the summertime and fall; whether worn without socks in the summertime or accessorized with funky ‘knee highs’ in the fall, this worldwide favourite is a multi functional gem! As we transition from summer to fall [OH WAIT IT’S FALL], I thought it would be fitting to present my lovely readers with ideas on how to make the transition a smooth one in a series of posts. Chucks are a great way to make that transition below your knees. Whether you’re a high top kind of girl or a low top lover like me, I want to introduce my three favourite ways to style this classic shoe. Check out the looks below and let me know how you like to style yours as well. If you are not a Chuck Taylor wearer let me know how you like to style your choice of canvas sneaker!

1. Chuck Taylor Sneakers with jeans – 

The most conventional way to rock your Chuck Taylor low tops are with jeans of course! I chose to pair my sneakers with a colored denim to add something extra! More structure can be added to a Chucks and jeans look by adding a blazer. It all depends on the look you are trying to accomplish. Play around with your Chucks, try on outfits, and find looks that work for you!

Chuck Taylor Shoes

Chuck Taylor shoes

2. Chuck Taylor sneakers with a Skirt – 

Who says you can’t rock sneakers with a skirt! Certainly not I ! This is probably my favourite way to style low top Chuck Taylor shoes. I love the sporty feel wearing Chucks with a skirt provides. If you’re looking for a less Obvious way to style your ‘sneaks’, I’d start here! The fun part in wearing Chuck Taylors with a skirt is that it can be done in so many ways. Whether you’re wearing a formal blouse and skirt with an abundance of accessories, or wearing a leather skirt and t-shirt like myself; It works! Personally, I prefer the less informal approach to wearing chucks and a skirt! Give me a graphic tee and structureless skirt and I’m GOOD! Which do you prefer?

Chuck Taylors, Forever 21

Chuck Taylors shoes, Forever 21

Chuck Taylor shoes, Forever 21

3. Chuck Taylor sneakers with a dress – 

Wearing your ‘sneaks’ with a dress can be done in a fairly similar way as option #2 [with a skirt]. I styled mine with an all black dress with cutouts which I normally pair with heels. In this case, I was looking for another way to make my dresses cross-functional. Pairing them with Chucks was the solution I came up with! These shoes work because of the material and the delicate detail of the shoe. Low top chucks are such a dainty shoe that can be paired with just about anything, so if you’re looking for an added way to dress-down a dress; I’d recommend styling with Chucks!

Chuck Taylor shoes

Chuck Taylor shoes

Oxblood Cambridge Satchel



Look 1: Forever 21 98′ Top || Chuck Taylor White Low Tops || Bougie Boutique Necklace || H&M Bag

Look 2: Dress || Chuck Taylor White Low Tops || Cambridge Satchel (Similar)

Look 3: Urban Planet Skinnies || Forever 21 baseball shirt || Chuck Taylor White Low Tops

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  • Reply September 25, 2013

    Purple Ivy

    its such a great piece to wear all year round. I always prefer it with a dress or shorts. I like how you styled it with the skirt too.


    • Reply September 26, 2013


      Thanks for reading boo! I prefer bearing a little leg with chucks too ! xx

  • Reply September 25, 2013


    Awww.. U jux shot me in the heart.. Loool… Ive alwaes loved any girl that wears chuck taylor shoes…. U r just too much…. I realy like this…

    • Reply September 26, 2013


      Aww thanks dear !!! Chucks are the bomb indeeed !!!!

  • Reply September 27, 2013


    Love both looks they are both great pieces for any season. love your first look with the leather circle skirt with a jersey girly but with a hint of tomboy.


    • Reply September 27, 2013


      Thanks Gorg! Your blog is great xx ! Keep in touch

  • Reply September 29, 2013


    I really like that brown leather bag

    • Reply October 14, 2013


      Thanks budd !! Thanks for visiting dear friend ;P !

  • Reply September 29, 2013

    Kim L.

    I love how you can pull off skirts and dresses with those chucks!
    I can never do so. 🙂

    accidental encounters

    • Reply October 14, 2013


      You soo can ! TRY hun! Thanks for visiting xx

  • Reply July 19, 2014


    I love how every look is so different! Amazing!

  • Reply October 6, 2014

    Meg Marshall

    I was actually thinking recently that I need a pair of white Chuck Taylors and I think you have positively inspired me to do so :).

    Love the outfit combos. We are Cambridge Satchel twins. I have a neon yellow one.

  • Reply February 7, 2019

    Laura Peinado Rodríguez

    Love the ideas!! My favourite is combining them with a dress!!

    • Reply March 13, 2019


      Thanks so much <3

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