Men’s fashion trends from the past 100 years


Men’s fashion trends from the past 100 years

While men’s fashion often resides in womenswear’s shadow in terms of exposure and versatility, menswear has a robust and dynamic history. Menswear trends through the years have served as time capsules that can hold the key sentiments of an era. The fabric of a jacket can hold clues to the political climate and a collar shape can signal the wearer’s occupation, while a wide-cut pant leg can signal a moment of social rebellion. From austere suits of the Depression-era 1930s and laid-back leather jackets of 1950s greasers to the shiny opulence of the 1980s, menswear trends have always been able to capture the spirit of the time.

Some menswear trends fade just as fast as they come about, while many have stood the test of time and remain fashion staples today. Some trends are born out of necessity, like detachable collars in the 1920s, and some from an era’s popular TV show, bringing back nostalgic trends from the 1960s ad-age. The cyclical nature of the fashion industry causes early trends to re-emerge in later years with minor tweaks or updates. The 1920s’ wide-brimmed fedora re-emerges with a narrower brim in the 2000s and the 1950s skinny tie brings a touch of nostalgia to suits in the 2010s. With a new decade underway, we may see a new resurgence of past trends (flip-flops, anyone?) intermixed with new, innovative looks.

Stacker compiled a list of 30 menswear fashion trends to pay tribute to the menswear trends that came before. The list contains trends that occurred during the last 100 years (from 1920 to 2019) using a variety of fashion analysis sources and news articles. Click through the slideshow to take a trip back in time through menswear fashion trends from the past century. 

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Charlie Huang // Wikimedia Commons

1920s: Detachable collars

In the early 1900s, it was customary for men’s shirt collars to be sold separately from the shirts themselves. The detachable collar allowed conservative businessmen to easy launder their collar and, if need be, replace them. They also offered the ability to change up the collar styling of a shirt. These collars were always white and stiffly shaped into a tall fold that could rise up to three inches tall. These detachable collars gave way to the term “white-collar,” which is still used today to characterize office workers.

National Library of Ireland

1920s: Wide-brimmed fedoras

The 1920s was a big era for hats, and by far, the most iconic style of the decade was the wide-brimmed fedora. The fedora was the preferred hat style of young men because it didn’t have to be matched exactly to a suit’s material. Men were able to mix and match their suits to their hats, allowing them to add some of their own personality to their ensemble. This trend would re-emerge with a more narrow brim in the 2000s.


1920s: Two-toned Oxfords

Unlike the basic design of oxford shoes in the 1910s, the two-toned oxfords of the 1920s added sporty flair to men’s footwear. With contrasting leather detail placed at the toe-cap, heel, and around the laces, this style was a departure from the somewhat conservative, utilitarian version before it. Versions of this trend are still worn today by both men and women.

Public Domain

1930s: Double-breasted suits

By the 1930s, boxy silhouettes emerged and double-breasted suits and tuxedos became the fashion of the decade. Suits of this era were cut with slimmer waists and tapered pant legs to conserve fabric during the Great Depression. Darker colors became fashionable, representing the sullen attitude of the era.

London Express // Getty Images

1930s: High-waisted trousers

Accompanying the era’s double-breasted jacket were high-fitting trousers. The higher waistline created a lengthening effect that balanced out the bulk of the pleated fronts. It was the extra-wide waistband that remained unique to the 1930s and is sometimes referred to as a Hollywood trouser. These trousers were meant to be worn with a vest or sweater.

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National Archives

1940s: Zoot suits

The 1940s brought World War II, and with it, a government restriction on wool. Because of this, most menswear was made to conserve fabric. This policy manifested itself in single-breasted suits and trousers without pleats or cuffs. As an act of rebellion, young people and people of color adopted the overly baggy, excessively long, exaggerated zoot suit style, rejecting the conservative nature of the time. Because they were technically illegal to make due to the excessive use of fabric, zoot suits were often purchases on the black market and became the uniform of the anti-establishment “swing kids” that hung out at jazz clubs.

Hulton Archive // Getty Images

1950s: Polo shirts

The end of wartime brought with it a more relaxed menswear style often referred to as sportswear or leisurewear. The 1950s introduced laid-back styles including the polo shirt, which was seen as a more youthful, casual alternative to the formal button-down style, while still maintaining a conservative, golf-style look. Polo shirts are still a solid fixture in a business-casual wardrobe today.


1950s: Motorcycle leather jackets

Just as the zoot suit was a rebellion against the thrift and conservation of wartime in the 1940s, the “greaser” style served as a rebellion against the social conservatism of the 1950s. A style mostly embraced by the youth of this era, greasers sported T-shirts, denim, and leather jackets. The greaser style was further popularized by James Dean in the iconic film “Rebel Without a Cause.” This style would re-emerge in the 1990s.

Chaloner Woods // Getty Images

1950s: Wayfarer glasses

Ray-Ban premiered the Wayfarer style in 1956, and it has since become one of the most popular sunglasses styles of all time. The trapezoidal shape of the plastic frames is flattering on a variety of face shapes and gained favor among celebrities like President John F. Kennedy, Bob Dylan, and Andy Warhol. To this day, Wayfarers are beloved by celebrities and non-celebrities alike.

Keystone // Getty Images

1960s: Floral prints

The social tumult of the 1960s gave way to various subcultures that were dealing with wartime injustices in their own unique ways—including expressing themselves through fashion. One thing was certain, convention was no longer the norm as the menswear industry began to embrace funkier prints and patterns, including florals. The age of Flower Power brought colorful floral shirts, ties, and even trousers into the realms of both formal and casual attire.

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1960s: Chelsea boots

One subculture of the 1960s was the Mod set, who took their minimalist fashion inspiration from London’s rock music scene. Bands like The Beatles and The Who brought the Chelsea boot trend to the forefront of men’s fashion. Everyone from young artists to business executives wore this sleek, slip-on style of boot.


1960s: Clubmaster glasses

Though the Clubmaster style of glasses first became available in the 1950s, the style gained peak popularity in the 1960s. Somewhat similar to Ray-Ban’s Wayfarer, the Clubmaster has a thick browline that receded into a thin lower rim. While the style faded from popularity in the 1970s, the show “Mad Men” revived the style in late 2007 by capitalizing on the cool nostalgia of the 1960s advertising culture.

Dove Daily Express/Hulton Archive // Getty Images

1970s: Bell bottoms

The 1970s were the age of disco, and with it came the rise of bell-bottom pants. With an exaggerated, flared leg, bell bottoms allowed for extra movement on the dancefloor and were worn in a variety of fabrics and patterns. The clothes of this era were highly influenced by the hit film “Saturday Night Fever.

SenseiAlan // Flickr

1970s: Leisure suits

The leisure suit was a decade-defining trend of the 1970s along with the rise of disco. It generally consisted of a boxy, poly-blend blazer, with several unnecessary pockets and matching pants. The look was most often completed with a loud button-down shirt — preferably made of qiana — with oversized point collars. At the time, it was considered a casual and cool take on the standard suit of the eras before. 


1980s: Loafers and boat shoes

The “Miami Vice”-inspired pastel suits of the 1980s were usually paired with a pair of loafers or boat shoes. Loafers and boat shoes were also popular for more casual looks as well. Both styles could complete a workwear look or add preppy flair to a casual outfit. Loafers and boat shoes remain timeless styles and are popular today.



1980s: Bomber jackets

The hit TV show “Miami Vice” premiered in 1984 and became a huge fashion inspiration for the menswear of the 1980s. So-called leisure suits became popular and consisted of a t-shirt worn under a designer suit, usually in a variety of pastel colors. This was a casual and cool take on the standard suit.



1980s: Denim jackets

The 1980s was a peak decade for denim, with many men embracing the head-to-toe look of wearing jeans paired with a denim jacket. The denim jacket could be paired almost universally with everything from a button down shirt to a t-shirt, from khakis to jeans. The denim jacket is still a versatile menswear staple today.


1980s: Sneakers

Drawing from the rise of hip hop music, sneakers became a major fashion trend of the 1980s. Most notably, the Nike Air Force One and Nike Air Jordan styles became huge commodities that would signal the beginning of sneakerhead culture. Additionally, the rise of the aerobics fitness craze made Reebok sneakers very popular during the ‘80s. Today, sneaker styles from that era are highly coveted collector’s items.


1990s: Graphic tees

The 1990s were a confusing time for fashion. Coming down from the excess of the ‘80s, the ‘90s were more about emphasizing casual comfort and street style. As a result, the graphic tee was worn by everyone from teenage skaters to off-duty businessmen.


1990s: Windbreakers

In keeping with the athletic-focused styles of the 1990s, the windbreaker became a street-style staple in menswear. Windbreakers of this era often featured bright colors and bold patterns. The windbreaker has made a recent comeback in today’s fashion, with men wearing them as a retro nod to the 1990s.

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1990s: Flannel shirts

The 1990s was the heyday of grunge. The flannel shirt soon became a uniform staple of the grunge subculture with celebrities like Kurt Cobain and Johnny Depp pairing flannel shirts with t-shirts and jeans.


2000s: Machine-distressed denim

Denim took a bold turn in the 2000s with the rise of distressed and faded jeans. Instead of letting jeans distress on their own through normal wear and tear, the 2000s brought mass-produced machine distressing that looked faded right off of the rack. This resulted in exaggerated displays of distressing and dying. Luckily, this trend faded away by the next decade.


2000s: Military wear and camouflage

The mid-2000s saw the United States once again at war, and the rise of military wear in regular men’s fashion followed. From cargo pants to camouflage patterns to army jackets, the military influence was undeniable. This trend still lingers, gaining steam in menswear trends every few years.


2000s: Bucket hats

In addition to military wear, bucket hats also gained huge popularity during the 2000s. With versions in original canvas, nylon, and even faux-fur, bucket hats infiltrated this decade’s popular culture with celebrities like Jay Z, Nelly, and Brad Pitt all seen sporting them. 2019 saw a strong resurgence in the bucket hat trend, with many gracing the runway that year.


2000s: Sport sunglasses

Eyewear in the 2000s took an athletic turn with styles that were originally meant for sports like motocross, running, and biking making their way into everyday wear. Frames were often outfitted with tinted lenses in various colors and shiny reflective coatings. Thankfully, sport sunglasses have since gone back to their utilitarian origins.

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2000s: Narrow-brimmed fedoras

The 2000s welcomed back the fedora hat into menswear, but unlike its classic 1920s predecessor, the brim of modern fedoras is very narrow. Clearly, this isn’t a hat aimed at sun protection. This narrow-brimmed style became a trendy staple on the red carpet throughout the early 2000s with stars like Diddy and Justin Timberlake sporting them in photos.


2000s: Flip-flops

In the early 2000s, along with the rise of the casual-loving Abercrombie set came the rise of men wearing flip-flops. Possibly one of the more controversial trends, flip-flops became perfectly acceptable to wear with jeans and a t-shirt (and in some cases, a button-down).

Jonathan Mueller // Flickr

2010s: Skinny ties

Skinny ties were originally a trend of the 1950s, but they gained a newfound popularity among young men in the 2010s. As all styles came to focus on slimmer silhouettes, so did neckwear. Though the style is starting to phase out, men still sport skinny ties today.


2010s: Analog wristwatches

With the fall of the digital watch came the resurgence of classic analog wristwatches. As the digital watch became associated with a style that was more casual and sporty, the analog watch renewed itself as the universal standard of upscale men’s wristwear.


2010s: Slim-cut denim

Originally made popular by 1960s rockers like The Rolling Stones, Bob Dylan, and The Beatles, slim-cut denim hit its true stride in the 2010s. This decade gave men’s slim-cut denim the designer treatment, with almost every luxury line creating a version of slim-cut men’s jeans.

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