90s Men’s Overalls: Trends and Outfit Ideas

90s Mens Overalls a Man Wearing blue overalls with a shite t shirt
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Last Updated on December 2, 2022

Overalls, more commonly known as dungarees during the 90s, are a type of garment originally created for protective workwear.


The classic overall is usually a dark indigo denim, but there are endless variations of fabrics used to create overalls, especially as they have evolved into a stylish garment rather than one to wear to work.

But you’re probably wondering:

Why were they so popular during the 90s?

During the 90s, overalls became one of the most commonly worn garments by everyone. This included all generations and income levels. Construction workers wore overalls, as did celebrities. Overalls are comfortable and cool. They give off an effortless vibe and are easy to style due to their versatility.

The Origin of Overalls


Overalls were invented sometime in the 18th century, but they hit the market as a fashion product in the 1890s. Throughout the years, they went from being a workwear garment to a casualwear fashion staple.

The first to mass produce them were Levi, Strauss, & Co. The first designs they released were simply jeans with suspenders. Throughout the 19th century and onto the 21st, the classic overalls with the bib on the top began mass production.

1920s and 1930s

Overalls are considered symbolic garments, and have formed part of important cultural movements throughout history. In 1920, overalls became linked to protesting against the escalating costs of purchasing clothing.

During the Great Depression in the 1930s, within the United States overalls became representative of low-income individuals who had been highly affected by the Depression. This was especially common in Western US.


In the 60s, the perception of overalls changed. They began being incorporated as official garments for the everyday rather than just as a work uniform. They are especially popular among youth, and had evolved into much more than just casualwear garments.

Some high-end luxury brands have incorporated overalls into collections and on runway shows. Contemporary brand catwalks such as Craig Green, Per Götesson, Sunnei, Ellus, and Dries Van Noten have included these garments within collection designs.

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Impact in the 90s

Due to their workwear related history, overalls offer an edgy aesthetic and represent a sense of masculinity, strength, and toughness. During the 90s, overalls became a massive trend that was popularized by rappers and multiple actors. They formed part of the hip hop aesthetic and the grunge aesthetic.

They were favored because they were low maintenance. They could be worn through all four seasons, with turtlenecks, hoodies, tees, tank tops, or alone. They were worn by both men and women but were recognized as a masculine garment.

Overalls were worn in oversized, loose styles—as per the rest of garments throughout the 90s following the idea of casualwear. Many people preferred to buy them second hand, for example at thrift shops. This way, the overalls were more worn, had gone through more washes, and appeared slightly faded.

Read: Men’s Jeans Brands and Trends from the 90s

Overalls come in all shapes and sizes, but the easiest way to change their aesthetic is the way they are styled. While overalls adapted to many different styles and subcultures throughout the 90s, the most popular among them was hip hop.

This style heavily incorporated overalls as a principle garment that was worn consistently, yet in multiple different ways:

Preppy Americana

There was a way to style overalls to make them form part of the preppy americana aesthetic. This was linked to the idea of new money within American society, and forming part of the high class by “making millions”. This was common among many rappers and songwriters.

The easiest way to create the look was to wear a striped jersey shirt underneath a dark wash classic overall. Accessories could include clean white sneakers and a snapback worn backwards. Hip hop icon 2Pac was known for favoring overalls, and was photographed wearing them in different ways throughout his career. Here he is wearing overalls in the preppy americana style.

To recreate the preppy americana look, in a more contemporary manner, pair these cobblestone washed classic denim overalls and this long sleeve stripped crew neck shirt. The look is simple to construct, highly comfortable, and apt for running errands, relaxing at home, or out on the street.

Sports Casual

It is no surprise that sportswear incorporated overalls, as this was also one of the most popular fashion styles throughout the 90s. An easy way to style overalls incorporating sportswear was to wear a graphic tee, printed overalls atop, and accessorize with a sports team baseball cap.

It was important that overalls be oversized, seeing as the shirt underneath could be seen almost completely. And if preferred, you could undo one of the buttons holding up the bib. Here is 2Pac once again, this time wearing very differently styles overalls.

To copy the sports casual aesthetic, choose an overall with a shorter than most bib, a casual graphic tee, and that classic NY Yankees hat with casual footwear such as sneakers. You can wear this look at a sports event, or even a get together with friends.

Classic 90s Youth

This has become one of the easiest to recognize fashion styles of all time. Anyone who sees images of classic 90s kids or young adults wearing overalls, immediately knows the image was set in the 1990s.

Will Smith’s role as The Fresh Prince of Bel-Air made him an icon of 90s fashion, one who represented the aesthetic of classic 90s youth. His hilarious role as Will’s success definitely had to do with his wardrobe and styling throughout the series.

One of the most iconic images shows him wearing overalls. He wears an acid wash cleanly structured overall, that is not as oversized as other 90s trends.

The overall is missing one button, causing the bib to be folded over. Underneath, he pairs the garment with a Hawaiian style button up shirt, and accessorizes the look with a simple black, silver buckled belt.

To replicate the classic 90s youth look, attempt to choose garments similar to Will Smith’s on The Fresh Prince of Belair. Go for a Hawaiian cotton button up shirt of any print you like, a light wash pair of overalls, and a simple black belt to tie around the waist.

Urban Streetwear

Overalls could also be styled as urban streetwear garments. This could be done through a variety of ways, all incorporating elements of urban or hip hop fashion with overalls to create this aesthetic. 2Pac was known for displaying this particular style on numerous occasions.

On a famous photoshoot, he wore a pair of loose, dark indigo overalls with the printed words ‘thug life’ painted white displayed on the center front bib. Underneath, he wore a dark, oversized hooded sweatshirt. He accessorized with chunky white sneakers, and a vertically stripped black and white beanie.

The overall look is original, and truly represents 2Pac’s ever changing style that has remained legendary, even after his death. This outfit represents the hip hop era, urban aesthetic, and the subculture of African Americans that rose to fame throughout the 90s.

To imitate the urban streetwear overall style choose a large hoodie, a dark wash pair of overalls that is very loose, a black Champion beanie, and your favorite pair of white sneakers, I love these Nike Air Max 90 Men’s Shoes. Classic and fresh!

This look is especially recommended for the fall and winter months, since it is adapted towards colder weather conditions.

Read: Champion Has Seen A Resurgence in Popularity: But Is It a Good Brand?