90s Fashion for Men – 23 Best 1990’s Themed Outfits for Guys



Men’s 1990s Themed Outfits. The ’90s were an iconic time for many reasons, the least of which being the wacky but very fun style trends. There were still some elements of the ’80s dominating the scene (loud sweaters, anyone?) but for the most part, men’s fashion was moving in a new direction and of course, we have all the pictures and footage to prove it. As of late, some of the most iconic trends have been making a reappearance… and if you are a guy who likes to keep up with the trends, then this article is for you. Not only will we talk about what those iconic trends were, but we are going to show you 23 outfits that you can rock today, all based around the ’90s themed style.



Sound good? Great! Let’s get started.

How to Dress 90s Style for Men

Some of the biggest fixtures of men’s fashion from the 1990s were cargo pants, biker jackets, casualwear, turtlenecks, snapback hats, and ripped jeans. Grunge burst onto the scene and it was all about edgy, casual street style. While some of those elements are still, arguably, prominent today, the ’90s were distinct in that these style choices dominated men’s fashion. So, with our outfits today, we are going to show you how you can modernize some of these trends to fit your 2020 wardrobe.

↓ 23. Velour Tracksuit

These bad boys were everywhere in the ’90s, rocked by such celebrities as Justin Timberlake and Puff Daddy (and Britney Spears, for that matter). To rock it today, it is just a matter of color, style, and brand. A neutral-colored Adidas or Nike tracksuit is a great option.



For more stylish gym outfits, check out these Men’s Workout Outfits.

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↓ 22. One-Strap Down Dungarees

For ’90s kids, The Fresh Prince of Bel-Air starring Will Smith was a show we all loved. And who could forget those wacky outfits? Here, Will Smith rocks the one-strap down look that was intensely popular at the time, along with an iconic button-down shirt and flat top haircut.

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To get a similar look in 2020, we recommend buttoning both straps of your overalls (unless you are a very confident guy, in which case, have at it!) and taking a page from Chris Pine’s book and opting for a neutral color like brown or black, worn over a white long-sleeved shirt. You can roll the cuffs on your overalls and pair them with some white high-tops. Add a baseball cap and sunglasses and you are good to go.

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↓ 21. Biker Jackets and Bleached Hair

A hallmark of the ’90s was a cultural obsession with biker jackets. Whether you were a guy who owned a motorbike or not, these leather jackets were all the rage and they added to the grungey street-style that exemplified the era. But it did not stop there. Just as famous as the biker jacket was the bleached hair trend. From Brad Pitt’s golden locks to Justin Timberlake’s curls, hair was just as much a part of what made the decade so distinctive as clothing was.

Here are some awesome Street Style Fashion Ideas for Men.

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Now, whether or not you decide to bleach your hair in order to honor a bygone era, you can certainly rock a biker jacket with ease. It is not hard to modernize the biker jacket trend at all. In fact, it is as simple as pairing up it up with a black turtleneck (another trend of the ’90s… score!) and some rust-colored corduroy suit pants.

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↓ 20. Rolled Cuffs

A crewneck sweater tucked into a pair of belted light-wash jeans is a look that could have been pulled straight out of Friends. (Pro tip: an easy way to gauge whether or not your outfit is ’90s enough is by asking yourself: would Chandler Bing wear this? Would Joey? Ross? No? Not ’90s enough.) We like how this look stays modern while also subscribing to some classic trends that give you the throwback stamp of approval.

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↓ 19. 90s Grunge Fashion

Are you a simple guy who prefers simple styles? A stripped-down grunge look might be the look for you. This all-black outfit is a piece of cake to throw together. Here are the best Men Ripped Jeans Outfits.

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↓ 18. Rolled Jeans and Lace-Up Boots

This rather daring look is quite iconic. It’s especially great if you have got the long hair to go with it!



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↓ 17. 90s Style Striped Sweater

A striped button-down sweater was a popular look 20 years ago. Here we see it as worn by James Avery on The Fresh Prince of Bel-Air.

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Here is a modern take on the striped sweater look.

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Here are 17 Ways to Wear Sweaters Fashionably.

↓ 16. Celebrity Style: Flannel Shirt over Graphic Tee

Zac Efron may have unintentionally rocked a popular ’90s trend, which is the open flannel over a graphic tee paired with jeans. He kept it modern by pairing it with Aviator sunglasses, mid-wash jeans, and a mod haircut. For more celebrity style inspiration, check out these 30 Hottest Pictures of Kenton Duty.

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↓ 15. One Pant Leg Rolled Up

Ah, yes, who could forget this iconic trend of the ’90s? Guys everywhere were hiking one pant leg up, whether it was jeans, joggers, or sweatpants. Think you’ve got what it takes to rock this look? If you are headed to a ’90s themed party, this is a fun way to give nod to the ’90s that your fellow ’90s nerds will love.

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↓ 14. T-Shirt and Long-Sleeved Shirt

If you have watched Friends, then you’ve seen this look before. The t-shirt over the long-sleeved shirt trend was best worn by Chandler Bing and it’s a great, understated way to give nod to the era. We especially love the extra detailing of chain hanging from the belt loop as well as the exposed socked ankles and dress shoes.

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↓ 13. 90s Style Baggy Jeans

Baggy jeans were an ongoing trend of the 1990s. They were popularized by musicians and then gradually made their way into the general public’s wardrobes.

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For a fresh take on the look, get yourself some harem-style jeans and pair up with a wide-striped sweater and forest green high-tops. This is a casual look that is subtle enough that people will have to do a double-take to figure it out.

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↓ 12. Travel Attire with Bucket Hat

An easy way to create a subtle ’90s vibe is by adding a bucket hat. We particularly like this look for traveling but you could certainly wear it to a party, to run errands or another non-formal event.

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↓ 11. Vertically Striped Shirt

Vertical stripe t-shirts were big in the ’90s. Such designers as Tommy Hilfiger, Eddie Bauer, and Polo made it popular. This is a great college look or themed party outfit. Pair a vertical stripe shirt with a crewneck tee, light-wash jeans, and white low-tops. For more cool and funky looks, check out these Men’s Yellow Pants Outfits.

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↓ 10. Sheepskin Leather Jacket

For your next casual business meeting, give a sheepskin leather jacket a try. This subtle throwback look will earn you major style points from men and women alike.

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↓ 9. Classic ’90s Look

Here is a classic ’90s look that you can easily imitate if you are on the hunt for throwback outfits.

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↓ 8. Classic Look with Flannel Shirt

Pairing a snapback hat with a flannel shirt is an easy way to create a ’90s look that still fits into a modern view of style. When it comes to snapback hats, wearing it forwards or backward will give it the 2020 stamp of approval. (Basically, what we are saying is: don’t wear it sideways. There is a line when it comes to flirting with ’90s fashion and you know you have crossed it the moment you twist that cap sideways.) Wear a white tee for extra era brownie points.

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↓ 7. What to Wear to a ’90s Party for Men

If you are headed to a ’90s themed party, you have an abundance of options to choose from – when it comes to wardrobe, that is… In the end, how committed you want to be to the theme is up to you. Whether you want to go all out or you want to keep it lowkey, we have got two options for you to showcase both ends of the spectrum. First, our all-out option. Not only is this a flashy outfit, perfect for a themed party, but how about that jacket and matching tie? From the colors to the fit, this pairing is super ’90s. Very Fresh Prince, too.

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If you are more of a subtle kind of guy, then you might prefer this lowkey option, which is less Fresh Prince and more Chandler Bing. We also like the Nike sneakers which add a bit of a modern touch to the look.

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RECOMMENDED: 14 Best Party Wear for Men for All Seasons.

↓ 6. Baggy Pants 

Few things say ’90s style like a pair of super baggy pants. Paired up with a graphic tee and some chunky skate shoes, this is a look you would probably see most days, sported by skater guys and your average Joe alike.

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Keep it fresh and modern by taking it in a loungewear direction. This super casual but very stylish look can be rocked at home or when you are heading out to run errands. Pair a white tee with some loose hemp pants in blue. You can wear this outfit with sandals or slides. Add a flat cap for that little bit of extra detailing.

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↓ 5. Summer Outfit with Bandana

Bandanas really came into their own in the ’90s as they were often worn by rappers to show gang affiliation. But the trend picked up and soon guys of all sorts were rocking a bandana tied around the head.

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It’s easy to incorporate a bandana into a summer look. Check out this 2020-approved ensemble that also works in some cut-off denim shorts (very ’90s) and a Coca-Cola motif tee.

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↓ 4. Mandarin Collared Shirt

Looking for a casual outfit for a business meeting? Try a mandarin-collared shirt. This light French-beige shade is pretty classic and you can pair it with jogger-style pants and white slip-on shoes. Going sockless is very European and will keep the look fresh and modern. Here’s a complete collection of Men’s Business Casual Outfits.

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↓ 3. Rayon Print Shirts

Ooh, baby, was this a look. Rayon button-downs in paisley and similar prints definitely defined the ’90s. These guys were paired up with colorful pants, flat top hairdos, and all kinds of footwear. Check it out and see what we mean.

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Now, this is definitely a themed look that will take a fair amount of confidence to pull off… but if that sounds like you, then why not give it a whirl? Whether you are headed to a themed party or just feel like spicing up club scene with your friends, keep the look fresh and distinctive by pairing your shirt with some black slim-fitting pants, white socks, and black dress shoes.

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↓ 2. Starter Jackets

Starter jackets were one of those things that crept over from the ’80s and redefined itself in the ’90s. Because colors were so distinctive in both decades, you can really get a feel for the era when you don a jacket like this in 2020. If you want to really throw it back, get yourself a starter jacket in some ’90s-approved colors: this combo of turquoise and purple was super popular.

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↓ 1. White Crewneck Tee Shirts 

White tee shirts were a hot trend of the ’90s as well. They were worn oversized with baggy pants, super tight with rolled sleeves, and under jackets, from denim to leather. You would often see such celebrities as Johnny Depp and Eminem rocking the white tee look and doing it with aplomb. They could also be worn with white jeans and black dress pants for a clean-cut street-style look.

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To modernize it is easy as pairing your tee up with a pair of distressed denim jeans and a denim jacket. You can roll both the cuffs on your jeans and the sleeves of your jacket up for that little bit of extra detailing that takes your outfit to the next level. Accessorize with a nice watch, some rings, and finish off your outfit with a pair of black-and-white Vans.

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