Styling Overalls for the New Age: Your 2024 Guide to Casual Cool

In the 1990s, the overall trend was a given. Icons like rapper Tupac and hip-hop artist Lauryn Hills, as well as R&B singer Aaliyah, popularized the look. The denim shape was first popularized in the US as an industrial workwear during the 19th century. It has evolved into a style statement with many variations over the years. In the 1970s, overalls were introduced with flared legs or fitted and cropped versions that could be worn without anything underneath. Olivia Wilde’s skin-baring, the free-spirited moment is shown below. Street style stars are reminiscing about the 1990s by wearing baggy pants legs, and sometimes even with one or both straps completely undone. Overalls are a new twist on deconstructed denim.

Hailey Bieber wore a pair of oversized Dickies, a brand that was also approved by Kourtney Kourtney. She wore them under a long duster coat on s date with Justin Bieber in Beverly Hills. She embraced the trend by adding sleek accents such as dark, thin sunglasses and a pointed-toe, sharp heel. There are many ways to wear overalls in all seasons, whether they’re worn as shorts, corduroy dresses, or distressed and rugged.

You may have been hesitant to wear overalls because you were worried about whether they looked flattering. After reading our guide, you will be able to wear overalls with lingerie for an evening at home or with heels. You’ll soon be wearing overalls as you would jeans. They’re comfortable, easy to slip on, and look great.

Hailey Bieber’s Style of Overalls

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Bieber wore baggy, light-wash Dickies overalls on a date in Beverly Hills. Justin was with her. Pick up a pair of distressed overalls in a couple sizes too large and layer them on top of a fitted white shirt. Finish off with a black duster coat, pointed-toe heels and a long black coat.

How to style overalls like Kourtney Kourtney

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Getty | Gotham

Kardashian was photographed wearing a pair of black Dickies overalls over a Blink-182 graphic shirt, a tribute to her husband Travis Barker. Finish your look with creepers, thick lug-soled loafers and dark skinny sunglasses to give it a similar ’90s feel.

How to style overalls like Olivia Wilde

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Getty | Hollywood To You/Star Max

Wilde showed off some skin in her overalls inspired by the ’70s, which featured a cropped leg and two pockets on the hips. These overalls are more fitted, and look great worn with a tube top or a tank. Wilde’s Ray-Ban shades and wedges were in keeping with her boho style.

How to wear overalls as pants

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Select overalls with a leg that is baggy, but that are fitted or adjustable on the hips to keep them up. Unclasp your straps and the top of the overalls will fold up over the waistband. This gives the appearance of denim deconstructed. The cropped blazer adds a touch of polish while revealing your midriff.

How to wear Overalls with 1 Strap

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Getty | Edward Berthelot

Slouching is the key to wearing overalls with just one strap. If you want your overalls to fall off your body, make sure they are baggy. Then, start with an interesting top, whether it’s a blouse with pouf sleeves or colorfully stitched. The majority of this top is visible once your arm is removed from one of the straps. Make sure that it coordinates with your entire outfit and speaks to your other accessories. Flip-flops completed the look in this case.

How to Wear Overalls in a 90s Style

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Getty | Edward Berthelot

The coolest pair of ’90s Overalls may have cargo pockets and a loop at the bottom. Start with a white T-shirt that’s breezy and finish off with platform sneakers to achieve the look most representative of the decade. Vans, Converse or Nike sneakers will all do. A backpack is also a 90s classic, so you can add one to your outfit.

How to wear overalls in winter

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Getty | Edward Berthelot

Layering underneath your overalls will provide you with warmth in the winter. A thick turtleneck is the perfect starting point. You can add a jacket √† la Bieber if you want, but a thick sweater will do. If your layers feel bulky, you can use a belt to tighten your waist once you’ve added the overalls. Timberland boots are functional footwear and allow you to tuck the leg of your pants if it is wet.

How to style men’s overalls

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Getty | Jeremy Moeller

Utility overalls with a rugged look, that may be distressed and painted, make for a great street style. Add a white t-shirt and a printed bomber jacket or varsity jacket to these overalls. Also, add oversized hoop earrings, a sleek boot and a printed varsity jacket.

How to Style Overalls for Work

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Getty | Daniel Zuchnik

The corduroy dress is our favorite overalls for work. It feels like fall. Layer your mini over a button-down shirt with a longer hem if it’s particularly short or skin-baring. The combination is a little schoolgirlish, but it’s instantly chic when paired with knee-high leather boots and a shoulder bag. This look can be made more luxurious by sticking to neutral colors.

How to wear Overalls Shorts

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Getty | Edward Berthelot

Shorts are a great way to dress up overalls in the summer. If you’re looking for a way to style overalls in the summer, shorts are a great option. Finish your street style with chunky sneakers or platform boots and a leather bag.

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