3 Ways to Wear Overalls Without Looking Like a Toddler

Your spring wardrobe texted me and it is very into this idea


There is looking young, or youthful, and then there is looking like Dennis the Menace. The thought of wearing overalls as an adult always made me feel like the latter. The last time I wore a pair, it was 1993 and I was inspired by the Nick Castle-directed Dennis the Menace movie. My interest in the style waned shortly after.

But then! The idea of styling them for grownups was broached in a recent editorial meeting, assigned to me (an aforementioned non-overall wearer) and so I said, “Okay.” Team spirit. It was high time I faced my overalls shit. I took a deep breath, got down to work and styled three pairs of overalls like a damn adult.

The first rule of overalls: Think of them like regular jeans…

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Madewell overalls, Tory Burch turtleneck sweaterZara jacket, Nancy Gonzalez shoes

The first thing to remember about overalls is that you don’t have to freak out and make a big deal about them. They are pants. Pants that happen to have a bib. Here we have Alisha in a sleeveless turtleneck top underneath a sequined jacket (I never said anything about not having the time of your life in these things) plus a pair of low-heeled kitten pumps to give a point to the otherwise boxy shape. Party outfit.

The second rule of overalls: Since they’re not regular jeans, remember they add extra interest…

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3×1 overalls, Everlane shirt, Mari Giudicelli shoes, Jennifer Behr headband

All I wear are white button-down shirts and high-waist jeans, but I wouldn’t shoot that for a “how to style x” story on Man Repeller. You probably have figured that one out for yourself. However! The overalls make the classic combo instantly more interesting, and because there’s so much denim, the bib tones down the giant headband of your choice. (See slideshow: I gave our girl an oversize portfolio clutch to adult the whole thing up. A “fun” bag might have been a little too hyper or something, you know?)

The third rule of overalls: Embrace the shirt underneath!

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Stella McCartney overalls, The Sleeper shirt, Laurence Dacade shoesGentle Monster sunglasses

Free your nips or don’t (just wear sunscreen either way), but do embrace a big ol’ blouse with puffy sleeves. It’s the anti-Dennis, keeping you far away from feeling like a toddler. You cannot overdo it here. The bib keeps everyone in check. A fun pair of shoes and lemonade shades add a LITTLE bit of a ’70s vibe, plus, they’ll make you feel like a kid again. In a good way!

Follow model Alisha Bansal on Instagram @alisha.b1. Photos by Edith Young; styled by Amelia Diamond with market assistance by Elizabeth Tamkin.

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  • Lotte Knapen

    Those platform sandals are amazing. But sandals that cost almost twice my rent are not an option. Anyone know of any knockoffs?

  • Aydan

    yes yes yes on the shirts underneath! I’ve been having a massive jumpsuit phase and now have so many “tank” jumpsuits! to keep them appropriate for work I’ve been playing around so much with the shirts underneath! deffo revamps the look!

  • Leandra Medine


    • Amelia Diamond

      thank you froog

  • Rachel Dlugatch

    Okay I know this is about overalls but I’ve been debating whether to buy that Zara stars jacket, and now I’m sold.

    • Amelia Diamond

      please get it, it’s really good in person

  • Kelsey Gockenbach

    I’ve been wearing my overalls a lot lately and my boyfriend keeps saying I look like a kid from the PBS show Zoom. #sorrynotsorry

    • cicillionaire

      Boyfriends don’t know anything. The only critique I ever get is “You should make it shorter.”, which doesn’t make any sense.

    • Amelia Diamond


  • cicillionaire

    Holy shit this is brilliant! I already own the best pair of overalls, and about a month ago I bought an over the top blouse with lace inserts and a long buttoned wrist cuff. The blouse is so perfect for those overalls! Why didn’t I think of this? Thank you!

  • Those Madewell overalls have been in my shopping cart for MONTHS

  • yasminenimsay

    What lipstick does she use in the “pollo” picture?

    • Alisha

      Cherry Balm Dotcom from Glossier : ]

  • Kay Nguyen

    You look amazing on those overalls! Great style <3


  • Hannah Cole

    you’ve convinced me. job done.

  • I’ve wanted a denim overall since Leandra wore a pair on her book cover, now I want a denim overall PLUS all of these clothes. Great job Amelia!!!!

  • StyleDebatesCom

    Let’s get 1970’s fashion back! Love all these looks, especially the one with a ruffled shirt and cool aviator sunnies! I also like the star printed jacket worn atop white denim overalls with ripped knees!
    xo, Jess | https://styledebates.com

  • Thanks for the tip 🙂
    Embracing the shirt underneath is the best tip.

  • Laura

    i found some great overalls at Baltimore-Paris, a french brand with a unique concept ! http://www.baltimore-paris.fr

  • Hellbetty666

    I’ve got the most wicked pair of dungarees with HUGE wide leg flares. Husband side eyes me every time I wear them. I have named them my Man Repellers as an homage to this wonderful site!

    I love to wear with a band shirt underneath. Wearing stuff underneath is definitely the way to go, if you have an infant’s bladder like I do!

  • Rheanonn Perez

    i like to wear mine with one strap unhooked for that “cool & relaxed” look. also so i can wear them at work without hiding my job’s logo + my name tag lol


  • doublecurl

    what about short overalls, is it possible without veering into toddler land?!?

  • Haley Fox

    so glad for this post! I sewed myself a pair of overalls a few weeks ago and am running out of ways to style