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I Can’t Stop Thinking About Hailey Bieber’s Denim Overalls 

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When denim overalls where at their peak 90s fashion zenith, I was five years old, wearing corduroy OshKosh iterations of the trend. Since I’ve grown out of my OshKoshs and into my adult wardrobe, I’ve been sorely tempted by the more glamorous adult versions I missed out on at the time.

During the 90s, Winona Ryder was the denim overalls champion. She wore them perfectly manic-pixie-tomboy-style with frayed edges, platform thong-wedges and woven bags. At 5’3, Ryder looked perfect in denim overalls. I’d grown out of my corduroys by the time Ryder’s Tumblr-friendly 90s aesthetic took hold of me. But, when I tried to copy her look I found denim overalls hugged my 5’9 frame in all the wrong places. I looked like a particularly busty and freakishly tall child (some would say I was).

Hailey Bieber wearing Dickies denim overalls with a long coat and heels
(Credit: Backgrid )

I put denim overalls in the “not for me” basket and moved on with my life. But then, this time last year Hailey Bieber stepped out in a pair. Bieber, of course, pulled a perfect high-low look by styling her classic Dickies with a $2, 800 Khaite coat and Totem mules. The 5’8 model looked perfectly chic (hell, even office-appropriate), and my denim fantasies were reignited.

The Denim Overalls In Fashion and Music

Originally a utilitarian clothing item, designed to protect the clothes of men working in mining, railroads and farming during the Industrialisation-heavy 1900s, denim overalls got a fashion makeover in the 1960s. College students, eager to align themselves with the working class adopted them as a fashion statement.

But the real revival that informed my dungaree dreams took place in the 90s.

Tupac Shakur
(Credit: Getty/Ron Galella/Ron Galella Collection)

Tupac Shakur arguably popularised the denim overall, wearing a pair of Dickie’s denim bib overalls embroidered with “Thug Life” throughout the 90s as a nod to his community. The bib overall became a sartorial statement in hip hop worn by The Fugees, TLC and Will Smith.

As is often the case, political moments in music are picked up by the fashion industry. In 1994, Kate Moss and Winona Ryder were both shot wearing denim dungarees and nothing else—Ryder was on the cover of Rolling Stone, and Moss was in an early shoot with Peter Lindbergh. From that moment, wearing (and pulling off) a pair of overalls became something of a sport for It-girls.

In the 2010s, as Jean Paul Gaultier and Ralph Lauren both sending overalls down the runway for their 2010 ready-to-wear collections, Alexa Chung and Chloë Sevigny skipped about in the even more challenging-to-wear American Apparell-ified micro-denim overall. 

Winona Ryder wearing denim overalls in the 90s
(Credit: TikTok: @coffinfortwo)

None of these iterations, worn either bare-chested or 2011 Terry Richardson-hosted Vice party-style felt particularly suited to my lifestyle.

But then I spotted 2020’s It-girl Bieber chicly out to dinner in the high-low look, quickly followed by Olivia Wilde pairing them with wet hair, a trucker hat, and Chloé-esque clogs while walking through a Los Angeles car park, and became convinced the adult overall may finally be for me.

Olivia Wilde is seen on June 8, 2023 in Los Angeles, California.
(Credit: Getty/Hollywood To You/Star Max/GC Images)

So, How Do You Pull The Denim Overall Off?

I turned to ELLE’s fashion editor Jordan Boorman; who better to ask than someone who makes clothes look good together for a job. 

She said the key to making the overall work is to keep it simple – resist the urge to doll things up with sky-scraper heels or a flouncy cottage-core shirt which can quickly start looking too agrarian. This may have been where I went wrong as a thrift-story happy 15 year old my first time round.

“Understated is the look you are going for, so lean into it,” says Boorman, referencing 90s style. She suggests pairing them with a basic white T-shirt and letting your shoe shape the vibe of the outfit. “Style with a shoe that suits the occasion, like loafers or a kitten heel.” 

The Best Denim Overalls Of 2024

Levi's Baggy Overall
(Credit: Levi’s )

01

Levi’s, Baggy Overalls

from $203.90 at REVOLVE

A classic loose leg overall from the brand that started it all this is the perfect knocking-about number for summer. Wear with boots or slides.

Key features:

  • 100% cotton
  • Bib pocket
  • 4 pockets
  • Adjustable shoulder strap
  • Side button closure
  • Logo detail on front pocket
Cream coloured denim overalls by Polo Ralph Lauren
(Credit: Polo Ralph Lauren)

02

Polo Ralph Lauren, Denim Overalls

$549.00 at The Iconic

Alexa Chung was such a huge fan of off-white overalls that she released her own in the now sadly discontinued “Alex Chung” line. Chung’s designs may no longer be available, but this creamy pair from Polo Ralph Lauren are perfect for channeling her relaxed style. Style with an oversized black handbag, sunglasses, Birkenstocks, or loafers for afternoon cocktails or summer barbeques.

Key features:

  • 100% pure cotton denim
  • Four pocket design
  • Square neckline
  • Available in winnie wash (pictured) and drey wash (blue)
x We The Free Ziggy Denim Overall
(Credit: Free People )

03

We The Free, Ziggy Denim Overall

from $156.11 at Revolve

The loose but tapered leg of these overalls provides a perfect balance to the slouch silhouette. We recommend wearing them cuffed with loafer and a plain white tee for summer.

Key features:

  • 100% cotton
  • Adjustable shoulder straps
  • Button closure at hips
  • Front and back pockets
  • Distressed detail
  • Ridgid denim
Jameson Women’S Utility Double Knee Overalls
(Credit: Dickies)

04

Dickies, James Women’s Utility Double Knee Overalls

from $93.10 at ($189.99) at Dickies

Dickies is one of the oldest providers of overalls in the business. First founded as “Clares” in 1900, has its roots in agricultural workwear but has since catered to the whims of the market and branched into more fashion-focused denim. Thankfully, its lifestyle apparel has kept its practical charm. Think a pencil divider in your bib pocket, room for a flask of whatever you fancy in the side pocket and buttons and hardware inspired by copper whisky stills. While many overalls are loose legs (and we love them for it), this iteration is perfect if you want a more streamlined shape thanks to its straight cigarette-style legs and slightly cinched waist.

Key features:

  • Straight leg
  • Double knee enforcement
  • Jameson-green triple stitching
  • Bib pocket has pencil divider
  • Flask pocket at side
  • Available in: botanical garden (green) and rinsed brown duck
  • Rigid denim
Ripe Denim Overalls

06

Ripe, Denim Short Overalls

$124.95 at Myer

If you’re going to wear overall shorts, we recommend going for a loose fit for carefree 70s comfort. We can imagine 2000s Ksubi model Bambi Northwood Blyth wearing these heavily distressed overalls, which incidentally come from Ripe, a maternity clothing range. Super relaxed they’re pregnancy friends with adjustable buttons at the side waist that can be extended, and adjustable straps. Pregnant or not this means you can tailor your adjust your look as you see fit.

Key Features:

  • 100% cotton
  • Colour designed to continually fade
  • Soft fabric
  • Adjustable waist and adjustable straps



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