Hey Chuck! Here’s Proof That Converse All-Stars Go With Everything in Your Closet

Feature image via Style.com

I can still remember getting my first pair of Converse All Stars. I was about 16, very into Fall Out Boy and indie rock, and I wanted to be cool. I had visions of late night adventures, going backstage, and becoming an it girl. To be quite honest, I probably thought I’d become Anna from the O.C. if I had them. Fame, fortune, and infinite je ne sais quoi would clearly follow my decision to buy a $50 pair of sneakers. Shockingly, none of this came true. But I did learn a valuable lesson. Chuck Taylor All Stars go with everything. Perhaps not an Oscar dress, but anything short of an extremely formal gown looks wonderfully laid back with a pair. Even a suit looks great with them! In a myriad of colors and a wide range of sizes, I’d go so far as to say they’re a wardrobe classic. Given that Taylors just underwent their first redesign in 98 years, it’s a mighty fine time to exemplify the ways in which you can wear these sneaks.

I’ve been wearing mine with jorts and cutoff tanks all summer long. How do you do your Chucks?

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Lydia O

Lydia Okello is a feminist, body positive, queer personal style blogger. On her website Style is Style, she showcases her panache for bright colors and power clashing. When she isn't pawing over Samantha Pleet collections on Tumblr, she's dreaming about havin' a kitten of her own one day. You can find her on Twitter, Tumblr and on her personal blog.

Lydia has written 64 articles for us.


  1. I love this so much :D
    I just got a wonderful pair in color “poolside”. They’re amazing :D. I’ll probably by them in a more classic color for the winter.

    It’s my first pair since I was 10 I think, and now my feet are a size 14 (US) and when I saw the shoes in this size I thought “damn that’s a lot of lacerows (there are seven pairs of eyelets. SEVEN.)

  2. True life: I wore converse to prom, and my then boyfriend asked if I was going to put on “nice shoes.” I honestly think that was more damaging to our relationship than my inherent gayness.

  3. Everything! Totally agreed. I once went off converse for a year or two exactly as my mum bought me them for Christmas. I cried a lot over those shoes because she couldn’t return them and i felt like such an ungrateful bitch. Still hurts my heart. She kept them for herself and then i took them back a few years later, wore them everyday and now they have such massive holes in i only wear them for seriously messy business like paintballing or cycling in the rain. So many feelings attached to one pair of shoes.

    • Just talking about this is making me want to ring my mum to apologise. I love them now, I’m sorry!!

  4. I’ve been addicted to converse since I got my first pair of hot pink ones in 5th grade! I now own possibly too many and have gone through several rounds of “dress-chucks.”

  5. I’m a sneaker head and collect Chucks. Honestly, I’d tell you folks how many pairs I have, but the number might be too obscene to some. Haha! My favorite pair are from 2002 and they have literally walked around the world and are still in service. It’s nice to know that my feet haven’t grown since my freshmen year of high school.

  6. I have an aversion to really flat shoes, so when I discovered they do a wedge version, all my shoe dreams came true!!!! I’m on 3 pairs and feel like I’ve been let into the cool-girl-club!!

  7. To my mother’s dismay, I wore pink chucks to my junior prom and bright red chucks with Spongebob Squarepants laces in my senior photos.

    However, I saw her yesterday and she had on chucks with a dress, so ten years later, she has finally admitted I was right.

  8. I need help: I have high arches and wide but very small feet (like 6.5D) and I want to love chucks, but they pinch and rub and are too flat and narrow for me and they only seem to come in a B width. Anyone else go through this? Any tips?

    • I usually buy the little boys converse for a comfort factor because I think kid’s shoes tend to run a bit wider. There’s usually a weird sizing difference between kid’s and woman’s sizes (like a kid’s 3 is a woman’s 5, or something like that). I have no evidence behind that other than my opinion, but I’ve only worn children’s shoes my entire life because I think adult sizes are so narrow and hurt my feet! Also, kid shoes are always cheaper. Maybe this could help?

  9. Umm screw not wearing them with formals! We’re both planning to wear some with our dresses when we get married next year, woo!

  10. Chucks are awesome. IDK how I survived all these years without a pair. I recently bought a pair of black ones for the gym because I noticed that I did better with weights with really flat shoes/no shoes, socks only. Then I started using them everywhere! Going out, with pants, shorts, house clothes. I’m contemplating on getting another pair.

    I’ve also been to some weddings where the bride and groom have Chucks on as well as their entourage. It’s cute to look at =)

    • Yes! I was at Costco this weekend & the lady in front of me noticed my high top zip ups (aces for airport security, btw) & told me about a wedding she went to where everyone was formal + Chucks.

      I’m leggings + skirts + Converse pretty much every day. And I’m 37 & work in local government. I developed a reputation for shoes with Fluevogs, which is what I wear if I’m going to be on camera, & then I can get away with Converse all the rest of the time.

      And I never pay full price: the secret is know your size & haunt discount sites & places like Ross.

  11. Ohhhh chucks <3 I got my first pair when I was 14ish, and they didn't really fit so basically my feet would go numb half way through the day but I wore them anyway. I've had them in my wardrobe ever since (but like, I have ones that fit now). Also I feel like they totally go with dresses!

  12. Wow, massive heart eyes for all the cuties in this post! It’s also making me miss Chucks since I switched over to keds for my wear-with-everything canvas shoe needs a little while ago.

  13. I have flat feet so wearing chucks is not a thing I can do without stealing the inserts from my boots and some convoluted re-lacing.
    What I’d do with them because they have pink accents was a Pink Ladies or Anybodys outfit, classic levis and open button up with an undershirt. After I got my black leather vest it was more Pink Ladies and I even wore them together with a high waisted pencil skirt kinda like Wanda.

    Got my chucks for my 14 birthday, the pink was making me uncomfortable at the time, then Katrina happened and they got lost in all the boxing madness so they are basically like new hardly worn and all that combined with the flat feet thing.

    Still I highly suggest pairing sexy pencil skirts with chucks for your inner Wanda or Pink Lady.

  14. black or white? which is more iconic and/or will match better? i rly need opinions cuz im bout to buy em

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