Men’s 90s Fashion

Written By Bakes

Avid writer on Men's Hair, Grooming, and Lifestyle!

With men’s 90s fashion coming back into fashion, it’s necessary to understand the in’s and out’s of this era in fashion. This article is a list of the most popular men’s 90s fashion.

The 90s were a great point in time for expressing creativity and, more importantly, fashion. The style and confidence of the 90s have always been held up to high regard. Consider the baggy over-sized clothing paired with statement pieces – shoes, bandanas, and the timeless leather jacket. The 90s were a time for men to shine. Sure, we had Naomi Campbell and Winona Ryder as fashion icons, but 90s Will Smith and Brad Pitt also stole the limelight frequently.

The 90s era of fashion featured a laid-back and chill vibe. People wore over-sized shirts and pants to get that cool-boy-on-the-block trend. There were a lot of oversized t-shirts and an even larger amount of denim. Denim was just everywhere – from jeans to jackets to shirts. In fact, denim on denim was not a sin in the 90s.

With 90s fashion rearing its head lately, more people are realizing the versatility of the era’s style. 90s fashion is making a major comeback, and for that, you need to sit down and get ready to study what works and what doesn’t in men’s 90s fashion.

In this article, we shall take a look at some of the most popular 90s outfits that you should seriously consider adding to your wardrobe. 


Most Popular 90’s Outfits You Need in Your Closet


1.  Bucket Hats

Bucket Hats

Number one on our list of essential 90s men’s fashion is the bucket hat. Incorporating the bucket hat into your outfit will be a no-brainer. It should be your first foray into men’s 90s fashion. If you are iffy about trying out 90s fashion styles, your best bet would be something small, like the bucket hat. It’s a statement piece that can transform your entire outfit.

Bucket hats are making a comeback in the 21st century. To be honest, the bucket hat has always been a functional fashion piece. It shields your face from the unforgiving sun. That’s why it’s a favorite among fishermen who need a piece of practical equipment to protect them from heat and light. The next time your outfit requires a cap, consider a bucket hat instead.



2.  Oversized Flannel Shirts

90s fashion for men

Sure, many people wear flannel shirts in this day and age, but are they oversized? 90s fashion dictates an oversized flannel shirt – whether thrown on top of a tee or tied around the waist. It’s the perfect look for a casual outing. It screams chill, and if you don’t want to be chill, then 90s fashion probably isn’t for you!

Pair a flannel shirt with a graphic or plain t-shirt under, some jeans, and a pair of comfortable Timberland boots for the perfect take on men’s 90s fashion. Bonus points if you can find the right grunge sunglasses and a breezy attitude. Wear these to hang out with the bros over the weekend.



3.     Leather

90s leather style

Leather never really left the fashion scene, but it’s getting picked up by the average dude. While before it was a statement for the grunge biker boys and rock bands, a leather jacket is now easily a staple in anyone’s wardrobe. Some people will wear their leather jackets as a signature part of their daily outfits, and why not – they are durable, comfortable, and most of all, they keep you warm.

The leather jacket is a timeless piece, but one that you desperately need if you want to be considered fashionable. You may not be a biker or part of an emo gang, but you qualify to wear one anyway. Leather jackets pair well with denim and boots.



4.  Overalls


Overalls were a statement piece in the 90s. Pulled off by celebrities like Will Smith, these will definitely draw attention. Overalls and dungarees are a bold look, and through the ages, they have been adopted by celebrities like Taylor the Creator and Chance the Rapper. They are a bold piece in men’s 90s fashion.

Even though overalls may not fit the bill for daily attire, they still have some charm. You can wear overalls for a lazy ice-cream date to show that you are bold enough to explore different outfits. Be warned though; overalls and denim dungarees won’t work for everyone.



5.  Snapbacks

Men’s 90s Fashion

Caps are cool. They shade you from the sun and add an element of style to your whole outfit. But in the 90s, caps or snapbacks meant something else. These flat-brimmed hats took the world by a storm. First worn by rappers, the snapback virus spread to the average guy. They are popular even today.

If you need to elevate your casual outfit for the weekend, consider wearing a snapback. It will pair well with a t-shirt, jeans, and sneakers. Choose bolder snapbacks if your outfit features muted colors; otherwise, the colors will clash in an unsightly mess.



6.  Double Denim

double denim 90s

Even though denim on denim is a big no-no in the fashion world, it was a raging hit in the 90s. Today, we are seeing a comeback of this trend that might ruffle a few feathers. Double denim is a fashion situation where you wear a denim jacket or shirt together with the same denim shade jeans. You can see why that would be a problem – it screams monotony and lack of creativity.

But, the 90s were a time for rebellion, and double denim fits the bill perfectly. Even though it might seem unsightly, you can pull off this look with a little finesse. Pair a lighter shade of denim for the top and a darker shade for the bottom. This will keep you looking classy but not out of place. Rock this 90’s look with a statement snapback and bold sneakers.


7.  Timberland Boots

timberland boots in hip hop

The Timberland boots trend is still ongoing. It was popularized in the 90s by hip-hop culture, specifically gangsta rap. This trend carried on to the 21st century, but it is now making a harder comeback. It’s quite rare to find one person who doesn’t own a pair of these time-tested boots.

These boots should be a staple in the average man’s wardrobe today. What’s not to like about the warm caramel color and sturdy design? Even better is the fact that it pairs well with anything under the sun. Any casual outfit is a contender for Timberland boots.



8.  Windbreakers

90s style for men

True to the era that made oversized clothing popular, we have windbreakers – a classic of the 90s. Windbreakers are the perfect article of clothing to protect you from wind, but that’s not all. These grunge pieces can be a fashion statement.

Bring back the 90s by investing in a daily-wear windbreaker for your outfit. Choose bold and blocky colors to make a statement. Add a bit of a sporty vibe to your outfit by throwing a windbreaker on top of a t-shirt and jeans. You can also pull off a look featuring a windbreaker and track pants—the ultimate sporty look.



9.  Oversized Clothing  (Jeans, Blazers, T-Shirts)

oversized 90s clothing

Gone are the days when oversized clothing meant you were wearing the wrong size. Oversized clothing is in once again! Sure, the 90s made oversized clothing hip, but later eras popularized clothes that actually fit. Now, however, we are seeing a rise in deliberately huge pieces of clothing.

Don’t be afraid to buy clothes that hang off your frame – no one will cancel you for it. Whether it’s jeans, blazers, or t-shirts, be confident in your outfit. It’s a tribute to men’s 90s fashion. Honestly, if you think about it, we are reclaiming 90s oversized style as just fashion. It’s back in, but it’s better than before.



10.  Athleisure

Men’s 90s Fashion (sportswear)

Popularizing athleisure has been attributed to the 90s. Before that, well, you could only wear it to the gym when working out. Fashion will take over even the most functional pieces of clothing for its own. And that’s what happened to athleisure. Forget functionality – enter fashion.

Wearing athleisure for a casual day is in season once again. Sure, you’re not hitting the gym today, but clothes are clothes! We are reclaiming this trend for the 21st century. Bust out your neon-colored track pants and converse shoes as an authentic ode to men’s 90s fashion.


11.  Sports Jerseys


The big names like Tupac and Biggy Smalls popularized oversized basketball jerseys as the new cool. Fashion claims all. Sports jerseys are no exception. It’s not uncommon to see movies from the 90s with at least one person wearing the famed basketball jerseys.

Today, we can reclaim the sports jersey. It doesn’t have to be oversized – just fitting enough to show off your form, but loose enough to be a tribute to the 90s. Pair your jerseys with a statement chain and sneakers to complete the look.



12.  Turtleneck

90s turtleneck for men

The turtleneck never really left, but it’s coming back bigger and better than before. The best part about the turtleneck? Anyone can pull it off. Turtlenecks give off an air of class and sophistication no matter who wears them. Teen stars and alpha males alike, the turtle neck fits just about any profile.

Definitely a statement piece; wear the turtleneck when you need to make a bold statement. Or when you need to keep your neck warm. 90s fashion may be coming back, but we still hold control over how we choose to wear it.



13.  Sneakers

Men’s 90s Fashion sneakers

Another item of clothing for men that changed the fashion industry for the better. Sneakers had to appear on this list. 90s sneakers gave birth to a new creative outlet for men’s 90s fashion. Sneaker culture led to the rise of the real cool boys. Cooler sneakers made you rise higher on the food chain. Fashion makes the rules.

Among the most popular sneakers in the 90s are the following:

Jordan’s: Made famous by 90s sitcoms featuring celebrities like Will Smith, Jordan’s remain a symbol of male fashion.

Adidas Superstars: Adidas sneakers made 90s fashion what it is today. They were the perfect pair for any casual outfit. T-shirt and jeans? Adidas. Denim dungaree? Adidas sneakers.

Converse: Converse sneakers are another statement sneaker that never really left the fashion scene but are seeing a hard comeback.



14.  Hair Styles

90s hairstyles for men

Clothes are great and all, but nothing screams the 90s like 90s hairstyles. Men’s haircuts from the 90s are interesting for sure, but they can be a hit or miss in the 21st century. Rare’s the man who can pull off the spiked and beached hairstyle of the 90s in today’s world. Still, some dare.

Needless to say, some 90s hairstyles for men are coming back in fashion. Consider the slicked-back hairstyle – this can be any gentleman’s daily look. You may see the mullet coming back too. Afros? Yes. Curly hair, bobs, bowl cuts – something for everyone who longs for the 90s.



15.  Accessories

Accessories might not be a word you associate with men’s fashion. But, the 90s men were adventurous, and this showed in their fashion. Bucket hats and snapbacks were all the rage in the 90s. Heavy chains were also a common sighting.

Loud, bling watches were starting to flood the fashion scene. Bold sneakers that defied all logic. Bandanas, that were originally used to identify gang affiliation. Men wore beaded necklaces. Sunglasses, leather gloves, bracelets! All these are relics of a bygone era that are starting to make another appearance.



Answering frequently asked questions on men’s 90s fashion

In this section, let’s answer some burning questions on men’s 90s fashion.

What can I dress up as for a 90s party?

A 90s party may call for anything oversized. Jackets, t-shirts, and jeans a size over will make the perfect outfit for a party to relive the old times.
Visit our what to wear to a 90s party editorial for more ideas.

What shoes were popular in the 90s?

The 90s were the time when sneakers started their rise to fame. Jordans, Adidas, and Vans became household staples. Additionally, combat boots also paired well with the leather jacket-wearing bunch.

What did men wear in the 90s?

Men in the 90s experimented a lot and went against the norm when it came to fashion. They wore a lot of oversized clothing and statement sneakers. They loved their bucket hats and bandanas. They claimed many functional clothes as fashion, including athleisure, basketball jerseys, and overalls.


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