Please show me your dresses with high tops?

The first two pics below are some white high tops I’m considering and would like to try them with skirts and dresses. I own the light taupe and pink ones in the last two pics and have some converse in navy and turquoise canvas. Lately I’ve been feeling like the canvas converse are less refined so I want to upgrade to leather. I’ve explored the forum and blog as well as Pinterest, but would love to see some photos of real people’s outfits. 

I usually wear midi to midaxi length dresses and skirts, and do have high arches so if you have better recommendations for sneakers I would love to hear them too. 

This post is also published in the youlookfab forum. You can read and reply to it in either place. All replies will appear in both places.


  • rachylou replied 2 years ago

    Those blossom ones are so pretty! (I don’t have any high tops, just wanted to say how pretty the blossom colour is :) )

  • Angie replied 2 years ago

    I wear skirts and dresses with hi-tops ALL the time! A wardrobe essential for my style. Here is one rendition in the pics. (Old pics of short platinum hair and red specs). 

    I only wear leather Converse. The canvas hurt my feet and ankles. Some of my Chucks are custom-made. VERY comfy. I add insoles too. I keep them light and crisp. Low contrast to my legs. White and pink are pretty to my eye, and work best with my wardrobe.

  • Lana replied 2 years ago

    Thank you Rachylou

    Angie, that is a fab look! I’m taking some time to think this through because with custom it takes a while but you get exactly want you want. I think white would be a perfect addition for me. 

  • Suz replied 2 years ago

    I can't wear Cons, alas, but over the years I've had two different pair of platform ones that  I wore with dresses and skirts and also cropped wide legs. A couple of examples below. 

    I think it tends to be a matter of proportion but most outfits that will work with low heeled booties should work with the high-tops. 

  • kellygirl replied 2 years ago

    I had a thread about this last year. It has some examples of my dresses with Cons. All of those dresses as well as the cons are still in rotation. I can't figure out how to link it but it was a WIW thread. I like them best when the whole shoe shows. I actually wore cons with a tiered skirt this week and surprisingly DH liked it. I guess it took him a year for his eye to adjust! Have fun with it. 

  • Lana replied 2 years ago

    Suz, That is a great tip about booties and high tops! Love your renditions.

    Thanks Kelly, I will go search for that thread and take a look.

  • Lana replied 2 years ago

    Found Kelly’s post:

  • Joy replied 2 years ago

    I have no high tops as they all rub painfully on feet or ankles, but the look can be an acquired taste.  Just do it and in time your eye will adjust.

  • Janet replied 2 years ago

    Kelly, Suz, and Angie wear this look well! 

    I tried and it doesn't work for me, but my body type is very different from theirs. With a skirt or dress, I need the ankle to show, or to be fitted with a bit of a heel, such as in a fitted bootie. I can do low-top sneakers with a skirt if I style the outfit carefully, but even that's not my favorite look on me. I stick with wearing my high-tops with cuffed/rolled jeans.

  • Jessikams replied 2 years ago

    I have really thick calves, so I don’t love this combo on me. ☹️

  • Kotosulamun replied 2 years ago

    I highly recommend you Pull&Bear snickers, they are great for high arches

  • Bijou replied 2 years ago

    I don't have any high tops, but I do wear dresses with my platform sneakers. This is a combination that I enjoyed wearing in summer.

  • Indigoprint replied 2 years ago

    Kotosulamun that is a fun resource. They have a nice variety of platforms. Thanks for sharing!

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