3 Ways to Wear Overalls Without Looking Like a Toddler

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.

Amelia Diamond

Amelia Diamond

Amelia Diamond is a writer, creative consultant, and Man Repeller alumnus living in New York City.

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