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How to Style Overalls

There’s workwear—a chore jacket picked up from a flea market, maybe some lug sole leather boots you scored off-season—and then there’s workwear. In the latter category, the uniform of farmers and fishermen alike, are overalls. The bib-style overalls we’re familiar with today date back to the 1800s, with roots a far cry from their fashionable come-up. Designed originally out of denim or heavy canvas for durability and function, overalls were strictly for work, and worn exclusively by men.

Cut to present day, and overalls with some sort of slouchy sweater seems to be the unofficial outfit of farmers market-bound weekenders. Wearing overalls without the intention of, say, tilling soil or chopping logs opens the garment up to a world of style opportunity. But where to begin? With zero stretch, according to Christina Grasso, a content creator and self-proclaimed overalls expert. “I personally prefer a pair that are very utilitarian and classic; I don’t like a pair without pockets or that feature any sort of weird proportions or detailing,” she says. She recommends overalls from Molly Dickson’s recent collaboration with Madewell, paired with a white T-shirt, a long black overcoat, simple black loafers, and a distressed Hermès Kelly bag.

Overalls are democratic, Grasso points out. “There aren’t many pieces that one can wear from birth through adulthood, and which can be styled and embraced by people at all stages of life, whether they’re farmers, painters, or disciples of Alexa Chung.”

Sarah Isenberg, an art historian with a thing for overalls, suggests searching for a vintage pair with an eye for waist and leg shape. Structured fabric is a must, she says. As for styling, the magic is in the opposition: “My favorite way to style overalls is to embrace feminine items to balance out the masculinity of the garment. I’ll often pair them with a ruffly blouse and Mary Janes to emphasize the contrast.”

Sarah Isenberg in her overalls.

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