How to Wear Converse in Almost Any Situation

by ParentCo. January 31, 2017

red and white colored sneakers

You may be wondering why you would wear Converse sneakers so often that you would need a guide for it. Fair question.

For starters, you can send the same messages with sneakers that you can with flats or heels: celebratory, outgoing, mysterious, even professional. Heels have a tendency of holding me back. For an ex-New Yorker who still walks fast, and now has to chase my toddler, I’ve become a bit of a sneaker evangelist.

Figuring out how to make sneakers work in various settings feels way more productive than forcing myself into shoes that stress me out. They’re generally accepted in most social situations these days: holiday parties, dates, play dates, networking events, and even the occasional wedding or job interview will allow it (the really good ones, anyway). Chucks can be paired with many levels of dressiness, provided you pair them with care.

Converse, in particular, can make you feel like an extrovert – especially if you aren’t. Something about their classic cool attracts people of all ages. I made the discovery when I bought a red, low-top pair on a friend’s recommendation. On a jam-packed meeting day, when I needed a mood boost, I wore them to work. (I should note that I am lucky to have the most casual of office-casual work settings.)

8 a.m. – Daycare

At daycare drop off, every toddler in the room came over in some sort of trance, pointing one sticky finger and saying, “Red shoes!” It was like offering fire to an ancient tribe.

9 a.m. – Coffee line at work

When I got to work, the first two coworkers I saw complimented my shoes and told me they’d had Chucks in college and missed wearing them. Extensive college reminiscing ensued.

10 a.m. – My desk

Two more coworkers approached and complimented the color of my shoes. Red is a big deal.

10:05 a.m. – My desk

A third coworker joined us and showed us all a photo of he and his wife sporting matching maroon Converse high tops. This started a heated debate: Is matching your spouse cute, or overkill?

6 p.m. – HOME...already!

Just about every meeting started with a friendly sneaker-related chat, setting an upbeat tone for the day. I made it through every meeting smiling.

When I dug into the history of the brand, it all started to make sense. Chuck Taylor All Stars have been around, in one form or another, since 1917. They went from basketball shoe, to Olympic shoe, to taking over 80 percent of the shoe market by 1957.

In the 1970s, fancier athletic shoes took off, and Converse became the rebellious choice for their simplicity. Which such a long history, they seem to hold a meaning for everyone.

So, I’ve developed some simple guidelines for wearing Chuck Taylors. In the spirit of the shoes themselves, I encourage rule breaking:

Consider color

1 | If you’re wearing brightly-colored Chucks (I recommend crisp red), make your outfit one of neutrals.

2 | If you’re wearing neutral Chucks, add a pattern, a pop of color, or unique accessory elsewhere in your outfit, and let the Chucks fade into the background.

Consider cut

1 | Because Chucks give off a laid-back vibe, make the item closest to them – your pants – a little more tailored. Skinny jeans work great, and a pair with a slight crop work even better.

2 | For skirts, anything above-the-knee or below-the-ankle looks good with Chucks. The midi-skirt generally doesn’t work. It creates too many horizontal lines across your leg in too small a space. This confuses the eye, and the effect can be disorganized when you’re trying to look pulled-together.

That’s it! Simple rules for a simple shoe.

A version of this article originally appeared on the author’s site,



Also in Conversations

family playing in pool
Before You Plan any Summer Adventures with your Kids

by Katelyn Denning

If taking adventures and creating fun experiences for your family matters to you, it’s possible to make it work. You just might need to shift your perspective.

Continue Reading

boy looking out the window
Getting Your Kid Ready for Their First Time Flying

by Jack Shaw

It’s natural to be anxious about how the flight will go and whether it will be as magical as the children had imagined. These tips will prepare your kid, and you!

Continue Reading

family on vacation
10 Ways to Ensure Your Next Family Road Trip is a Success

by ParentCo.

Family road trips don't have to be a National Lampoon-esque disaster. Especially if you keep these tips in mind.

Continue Reading