Men’s Style And Fashion In The 90s

The 90s fashion trends are slowly coming back into popularity, therefore it is important we understand what was in and what was out during this time period.

It is known that the 90s was a great time, when people started to express themselves more creatively through their style and fashion choices. 

Men’s Style And Fashion In The 90s

During the 90s was a great time for men’s fashion, with iconic artists such as Brad Pitt and Will Smith leading the way. The overall style of this era was much more chilled and laid back.

Thus, you would see men wearing oversized clothing and lots of denim. 

More and more people are realizing how good the fashion in the 90s was. Therefore, more of that 90s fashion is starting to make its ways back into the modern day.

In this article, we will discuss some of the most popular fashions trends that were seen in the 90s that you may want to consider  adding to your own wardrobe as well. 

Bucket Hats

When people think of 90s fashion trends, one of the top things they will think of is bucket hats. It was seen as an essential time to have as part of your wardrobe. There weren’t many places that people didn’t go where they wouldn’t wear a bucket hat. 

If you are just dipping your toes in men’s 90s fashion, then one of the first things you need to consider is the bucket ha, and finding ways of adding it to your outfits.

The bucket hat was seen as a statement piece of clothing, which could make a real impression, depending on what it was paired with.

A bucket hat could transform an entire outfit easily. It is also a great way of adding an extra pop of color to your outfit, to help make you stand out. 

The bucket hat has always been popular, and since its rise in popularity, it never really went away. Commonly you will see bucket hats being worn at festivals, as not only do they look great, but they are practical as well.

A bucket hat protects your head from the sun and also shields our eyes from sunlight as well. 

For younger generations, this hat is a great addition to their festival or gig outfit. However, this hat is also loved by fishermen as it protects them from the glare of the sun.

Thus, if you are considering purchasing some headwear, you should consider a bucket hat, as a versatile and stylish choice. 

Oversized Flannel Shirts

A lot of people can be seen wearing flannel shirts, but not all of them oversized. Yet in the 90s, an oversized flannel that is tied around the waist or placed over a shirt, was seen as the perfect casual going out outfit.

This was seen as the perfect relaxed outfit, that also looked really cool and trendy. 

In addition to this, a really great way to wear an oversized flannel shirt is with either a plain t-shirt or a graphic t-shirt. Then all is needed is some comfortable jeans and a pair of Timberland boots. That creates a classic 90s outfit. 

Leather Jacket

Leather Jacket

Leather has always been a popular fashion choice, yet it’s now becoming a more universal choice for all men. Before, leather was left more for rock bands or grunge biker boys.

However, today, a lot more people have a leather jacket in their wardrobe. When it comes to a leather jacket, for a lot of people, this piece of clothing is their signature item of clothing to wear with a range of different outfits. 

A leather jacket is ideal for casual wear and your daily outfits. This is because they are comfortable and durable. In addition, to keep you warm.

As a result, the leather jacket has become a timeless piece of clothing that never really goes out of fashion. Just because you aren’t part of an emo gang or biker gang, that doesn’t mean you can’t rock a leather jacket. 

A denim outfit with boots and a leather jacket, is the perfect 90s outfit, that is perfect for the modern day. 


A lot of celebrities in the 90s, such as Will Smith, were often seen wearing overalls. Both dungarees and overalls are a very bold fashion statement that in the past few years have slowly come back into fashion.

Throughout the years, overalls have been sported by a range of different celebrities, including Chance the Rapper. When it comes to 90s fashion for men, there isn’t a bolder statement that you have made than wearing a pair of overalls. 

With that being said, overalls aren’t for everyone. They aren’t suitable for every kind of situation. A lot of people may wear them occasionally as day wear, or some men may whip them out for special casual events. 

Either way, overalls are a great way to be more experimental in your outfits. As you can pair your overalls with a simple t-shirt o a more graphic t-shirt. 

Snapback Caps

The 90s were all about their hats, first with the bucket hat and now with the snapback cap. Caps were seen as really cool, as not only did they add some style and an edge to your outfit, they also helped shield your eyes from the sun.

Thus, they were practical as well as being stylish to wear. 

During this time, snapbacks were everywhere, and everyone had at least one cap in their collection. They were first worn by various rappers, which then caused everyone else to want to have one, so they could be as cool as their favorite rappers.

These hats are still really popular even today, the demand for them hasn’t dropped yet. 

A snapback can really evaluate your outfit of choice. Paired with a baggy t-shirt, jeans and sneakers. The color of your cap can really enhance the look, whether that is choosing a color that suits the colors you are already wearing.

Or if your outfit consists of very muted colors, then a bright or colorful cap can add a splash of color to your plain outfit. 

Double Denim

Double Denim

For a lot of people in the fashion world, double denim is considered a huge mistake, and something to avoid. However, during the 90s, denim on denim was a really popular sight.

Now, this trend is slowly coming back, but not to everyone’s happiness as the fashion world sees double denim as a gray area on whether you really should be doing this. 

Double denim is when you wear two pieces of denim clothing together. This could be a denim shirt or jacket alongside a pair of denim jeans.

Normally, all these pieces of denim will be the same shade of blue or black as well. This causes an issue for some people, as it is too much of one color of a person, and isn’t seen as very creative either. 

However, in the 90s, it was seen as a time when people wanted to rebel against the norms. Therefore, double denim fit these criteria and become a really popular fashion choice.

With that being said, there is a way to make this a fashion trend. That is, by wearing lighter or darker shades of denim together. This way you will break up the denim by the different shades. 

Timberland Boots

The hip hop culture in the 90s made Timberland boots a really sought after product. Still today, there is a huge demand for Timberland boots, but in more recent years, the trend is coming back bigger and harder than before.

It is now considered quite rare for someone not to own a pair of Timberland boots.

Originally, these boots were created for construction workers, yet rappers decided to wear them in their music videos. This caused all of them to want to wear a pair of boots like their favorite hip hop artist.

Nowadays, Timberland boots are seen as a staple in a lot of men’s wardrobes. They are ideal to be paired with any casual outfit, and they are incredibly durable.

Therefore, a pair of Timberland boots can last you years before you need to think about replacing them. 


In the 90s, oversized clothing was really popular. Something else that was really sought after was windbreakers. The windbreaker was seen as the ideal piece of clothing to have, due to their bold designs that made them look cool to wear.

In addition to that, as their name suggests, they keep you warm and protected from the wind. 

You could find windbreakers in a wide range of colors and designs. All of these options would be bold and eye-catching. In addition to this, a windbreaker always gives off a sporty vibe to an individual’s outfit. 

It is up to you how you pair a windbreaker with. You could throw it over a plain t-shirt and a pair of jeans. Or, it works just as well paired alongside some sports pants for the ultimate sporty outfit. 

Oversized Clothing

Oversized Clothing

For a long time, oversized clothing just meant you had brought and were wearing the wrong size for your body. Now in the modern day, oversized clothing is a huge fashion trend.

In the 90s, oversized clothing was made popular, but it was after that time period, where the trend really grew, and now it has stuck for the time being. 

We are now seeing people purposely buy clothing that is far too large for them. A lot more people are wanting clothing that doesn’t cling to their body, but instead hangs off their bodies instead.

To this day, you can still find oversized t-shirts, jeans and blazers, which can be enjoyed by anyone and any body type. 

This craze started in the 90s and after that just gained more and more popularity. 


Athletic wear like tracksuits before the 90s could only be worn when going to the gym to work out. Instead, the 90s made it popular to wear athletic wear any day, as a casual outfit.

Fashion brands took on this trend and started creating more comfortable and stylish sets for people to want to wear out and about. 

No longer was athletic wear just for functionality, it became a part of everyday fashion. Even today, it is still really popular to wear some form of athletic wear as your everyday clothing. Today, clothes are just clothes, no matter what their function is for. 

Sports Jerseys

Sports jerseys were really huge in the 90s. They were made especially popular by the rising hip hop culture within the 90s as well. Big names in the 90s such as Biggie Smalls and Tupac helped popularize oversized sports jerseys.

They were finally seen as the cool thing that everyone should wear. 

In a lot of 90s movies, you will see a lot of characters wearing some kind of sporting jerseys, especially a basketball jersey. These jerseys were always oversized, however, today sporting jerseys are becoming popular once again, but they don’t have to be oversized. 



The turtleneck has never not been in fashion, but some years it is more popular than others.

A lot of people are scared about whether they can pull a turtleneck off yet, and the thing is that turtlenecks are universal and no one can look bad when wearing them. 

By wearing a turtleneck, you instantly appear more sophisticated. During the 90s, a lot of alpha males and teen stars were seen wearing turtlenecks, which shows that anyone can look good in one. 

Alongside that, they are seen as a statement piece of clothing that draws your eyes due to the bold colors that they can come in. Don’t be scared to wear a turtleneck, as not only do they keep you warm, they make a strong statement and impression. 


Where would any man be without their sneakers? This item of clothing has changed the fashion world forever. This is because the sneakers from the 90s allowed men to express themselves more creatively.

A culture began for sneakers and led to the development of the cool boys that would have the very best and stylish sneakers possible. If you had cool sneakers, then you were seen as better by your peers. 

Some of the following were the most popular sneakers that you could own in the 90s:

  • Jordan’s – These were made more popular due to sitcoms in the 90s, and celebrities like Will Smith. Today, Jordan’s are a very strong symbol of male fashion. 
  • Adidas – Adidas were the perfect sneakers in the 90s, as they could go with any outfit of your choice. 
  • Converse – Converse were seen as a sneaker that you could make a statement with. They are still popular today for the same reasons.   


90s fashion was a fascinating time, but hairstyles also fall under this category. Especially as the 90s had some interesting hairstyles that are slowly becoming trendy once again today.

In the 21st century, a 90s haircut can be hit or miss, but some hairstyles come in and out of fashion all the time. Some of these hairstyles include the mullet, bobs, bowl cuts, spiked hair and Afros.

Over time, we may see more of these hairstyles making a comeback. Just like with fashion, hairstyles also come in and out of fashion.


Back in the 90s, men were a lot more adventurous and willing to take more risks with their fashion. As a result, accessories such as bucket hats and caps were all the rage.

In addition to that, thanks to the hip hop culture of the time, really chunky chains were a really popular accessory in men’s fashion. 

Not only that, but you could see a lot of men sporting large watches. Everything about men’s fashion and their accessories was big and loud.

Bandanas, leather gloves, bracelets, and sunglasses, all of these were common accessories in men’s fashion in the 90s. They weren’t afraid to try something different and express themselves in what they wore. 


Men in the 90s were willing to take risks in what they wore, and that can be seen in the popular fashion trends.

A lot of these trends are becoming popular once again today. This article has shown you the biggest fashion trends for men in the 90s. 

Joseph Pais