18 Bold Fashion Styles of the ’90s We Sorely Miss

By

Andreas Jones

Hey! I’m Andreas Jones and I am the founder of KindaFrugal.com. I’m passionate about all things personal finance, side hustles, making extra money, and lifestyle businesses. I have been featured in major publications such as Forbes, Entrepreneur On Fire, Lifehack.org, Influencive and Goalcast.

| Published on September 4, 2024

Brunette wearing Denim Overalls

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Do you ever look at old pictures of yourself and think, “Geez, what was I thinking wearing that?” Don’t worry, you’re not alone. Gen Z is picking up right where you left off, bringing 90s fashion front and center once again with Bold Fashion Styles that make a statement—just like they did back then.

It’s true. Just like history, fashion repeats itself with some modern updates. Maybe we never learn, or maybe there was something we missed worth revisiting. Either way, reflecting on styles of the past is a great way to gain inspiration for the future—or at least that’s what designers have been doing for generations. 

I’ll admit it: I’m a product of the 90s. I lived through most of these fashion trends and am proud to admit I rocked a few of the iconic looks we included on this list. Now, when I see how Gen Z Teens are wearing these styles, it gives me hope that maybe those old pictures weren’t so bad after all. What do you think of some of these 90s fashion trends? Are they worth bringing back?

1. Chain Wallets

Man having Chain Wallets
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If you were rocking some JNCO Jeans, you had to match them with a chain wallet. Chain wallets let other people know that you were tough, but they also made it practical not to lose your wallet in the gallon-sized pocket of your jeans.

2. Combat Boots

Woman wearing Combat Boots
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For some reason, I remember every “edgy” girl had to have a pair of combat boots. And these combat boots had to be Doc Martens. The “edgier” you were, the higher the boot wet up your leg. Watch out for the knee-high boots. Those girls would break your heart and then stomp on it.

3. Unbuttoned Shirts Over Graphic Tees

T-shirt under shirt
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This was how you spot the cool guys on campus. You had to find the best band tee you could find and throw a long-sleeve button-up over it. If you were really confident, you could roll up your sleeves. But, under no circumstances should you cover up that band tee.

4. Solid Tees Under Blazers

Solid Tees Under Blazers
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The same guys who wore the unbuttoned shirt transformed into these guys when they went out at night. Loose, baggy suit pants with a solid black tee under a sports coat were the look on a weekend night. Pair that with a nice gold chain to seal the look.

5. Reebok Pumps

Reebok Pumps
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Whether you were playing a pickup game on the courts or playing during recess, everyone knew that peak athletic footwear had a pump on the tongue to add extra air to the soles of your sneakers. These shoes made you run faster, jump higher, and make the other guys on the court jealous. I still think I would have made the junior varsity basketball team if I could have afforded those Reeboks!

6. Overalls

There were times when overalls weren’t just for toddlers or farmers. The hip-hop trend of wearing overalls with either one or both straps down was a fashion statement of the decade. Pairing it with a flashy shirt underneath was even cooler, but the really hip guys went shirtless. It’s funny because that’s how many toddlers and farmers wear them too.

I feel like a bucket hat would be a good hat to add to those strap-down overalls. Think of how cool LL Cool J made those hats look. Not everyone could pull them off, but a lot of people tried. If I wore a bucket hat, I would look more like Gilligan than LL Cool J.

8. Scrunchies

Woman using Scrunchies
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All the cheerleaders at my school had the brightest colored scrunchies around their ponytails. You didn’t want a small hair tie that no one could see. You wanted a tye-dye or acid-washed jean scrunchie to show off your style. Plus, when your hair was down, you could use it as a stylish wristband!

9. Flannel

Man wearing Flannel Shirt
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Grudge music was really popular in the 90s. With bands like Nirvana and Soundgarden coming from the Pacific Northwest, they brought their style with their music. Flannel was everywhere, and all the rockers needed to match their flannel to their ripped jeans. Also, you only buttoned up your flannel if you were a lumberjack.

The mid-nineties saw a rise in Tommy Hilfiger’s apparel. Musical artists like Puff Daddy and Alliyah were decked head to toe in the brand. Of course, the masses copied, and the red, white, and blue clothing was everywhere.

11. Sheer Clothing

Woman wearing Sheer Clothing
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If you were to look at some of the celebrity’s outfits in the 90s, you might notice a lot of them were see-through. Wearing a crop top with a sheer “shirt” over it was considered a cool look. I remember these shirts from watching the MTV Video Music Awards as a youngster.

12. Jansport Backpack

Jansport Backpack
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For some reason, I felt like having a trendy backpack in high school meant you were cool. All the cool kids had a JanSport brand backpack. This was the iconic brand to keep your school stuff in. You could also get them with graffiti on the back pocket if you want to make a statement. The only general consensus was that if you had one of these backpacks, you only had to carry it over one shoulder and one shoulder.

13. Bike Shorts

Woman wearing Bike Shorts
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Today, leggings or yoga pants are among women’s most worn articles of clothing. The 90s started that trend with bike shorts, which were commonly worn. Most of these were in traditional bright and neon colors, and both men and women wore them. Looking like you were ready to hop on your bicycle and ride around town was a hip look back in the 90s.

14. Skater Tees

Boy wearing skater tshirt
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The way to prove you were a skater when roaming your high school campus was to have some fresh skater tees. Some of the coolest brands were Alien Antfarm, Toy Machine, Thrasher, Spitfire, and Hook-ups. I can vividly remember that smiling flame face on the shirts of all the kids skateboarding in the local mall’s parking lot.

15. Body Piercings

Woman with pierced lips
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Body piercings gained a lot of momentum in the 90s. More and more musicians were getting piercings, which meant the impressionable youth were doing the same. Piercings began to be a fashion statement. Girls would wear crop tops to show off their sparkly belly button rings. Guys and girls had hoop earrings and pierced tongues that they couldn’t wait to show off. The piercing trend never really goes away after the 90s.

16. Slap Bracelets

Slap Bracelets
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This brings back a core memory from my adolescence. These simple metal bracelets, wrapped in colorful designs, are slapped around your wrist. They were the craze. I knew girls would have three or four of them on at once. That constant slapping must have driven teachers and parents crazy.

17. Backward Cap

Young man wearing Backward Cap
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You can thank rapper Chuck D, Will Smith, and baseball phenom Ken Griffey Jr. for making the backward cap a fashion statement of the 90s. Wearing your cap backward showed you were hip and edgy, and the rules of society didn’t belong to you.

18. Air Jordans

Air Jordan sneakers
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There was no bigger basketball player in the 90s than the Chicago Bulls’s Michael Jordan. The man won six NBA Championships that decade, so of course, we wanted to wear anything with his name or logo on it. Every year, people would rush to get his shoe. This brand still lives on, but the 90s might have been the best era for Jordan shoes.


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