32 Regrettable ’90s Guys Fashion Trends

Nobody ever pulled off JNCOs.

1. Overalls with one strap down.


Nothing said, “I’m a badass not a farmer,” like having one strap down on your overalls. In reality you just looked like you were one of the Little Rascals.

ID: 3408573

2. Hip-Hop Looney Tunes T-shirts.

AKA the most “urban” gear a lot of kids from the suburbs ever wore.

ID: 3408807

3. Skechers Chrome Dome.


The shoes that put Skechers on the map! It’s oh-so-mid ’90s design was a weird cross between a hiking shoe and a sneaker. Plus, they were also chunky!

ID: 3408635

4. Middle part bowl cuts.


Literally looking like a butthead.

ID: 3408669

5. Oakleys Eye Jacket sunglasses.

Probably the most coveted sunglasses for guys in the ’90s — they were also terribly unflattering. Unless you wanted to look like a bug.

ID: 3408568

6. Backwards baseball hats.

Literally, from 1990-2000, the only people who could read your hat were the people behind you.

ID: 3408683

7. Hemp necklaces.

These were basically the ’90s equivalent of chokers for guys; except they were incredibly itchy and the wooden beads would painfully press-up against your Adam’s apple.

ID: 3408792

8. Caesar cuts.


We can all blame George Clooney for this trend.

ID: 3408688

9. Flannel tees/ Plaid short-sleeve shirts.

Ugly plaid wasn’t just for flannels thanks to these short-sleeved shirts.

ID: 3408734

10. Hoop earrings.

Yo-ho, yo-ho, a pirate’s life for ’90s me!

ID: 3408730

11. Bowling-inspired shirts.


Could these shirts have BEEN anymore big and shapeless? Also, you could probably blame Swingers for the rise in popularity of these shirts.

ID: 3408841

12. Socks with shower sandals.

And the sandals had to be Nike or Adidas, no exceptions.

ID: 3409275

13. Kangol hats.

Paramount Pictures / Via pattygopez.buzznet.com

The ultimate cool guy hat, which, let’s be honest, you thought you could wear with anything. For school? Yup! For date night? For sure! For a wedding? Duh, it looks fly with a suit. The reality, Samuel L. Jackson is the only living person who can successfully pull off a Kangol hat.

ID: 3409103

14. Fanny packs.

I mean, what else were you supposed to carry your pogs and Game Boy in?

ID: 3408960

15. Pagers.

The ultimate baller-status accessory. Of course, it was important that you clip it on the outside of your pants so that everyone knew you had one. Maybe you even kept it safe and looking extra stylish by attaching it to your pants with a chain.

ID: 3409040

16. Wale cords.

The perfect way to let everyone know you were coming by the not-so-subtle zoosh sound they made as you walked.

ID: 3409065

17. Overly baggy jeans.

If ’90s guys had one style motto when it came to pants it would be: THE BAGGIER THE BETTER. Of course, you also looked ridiculous walking around with pants so big that they were difficult to even keep up.

ID: 3409158

18. Levi’s “Button Your Fly” shirts.

Who thought this was funny? Oh yeah, the same dudes who rocked those Looney Tunes T-shirts.

ID: 3409120

19. Acrylic striped ski sweaters.


These sweaters weren’t just hot and itchy, they were also not the greatest quality (no matter how much you paid for them). They usually looked pretty ratty due to the horrible amount of pilling they would get — after wearing them just once!

ID: 3409817

20. Big, fat, chunky skate shoes.

Which you probably wore without ever setting foot on an actual skateboard.

ID: 3409175

21. Fat laces.

Big-tongued chunky sneakers needed equally as big laces to go with them.

ID: 3409428

22. Bucket hats.

The perfect accompaniment to that windbreaker you got at the thrift store to complete your On Golden Pond look.

ID: 3409201

23. White crew neck T-Shirts under everything.

Time & Life Pictures



A blindly white T-shirt was a ’90s essential whenever you wore a button-up or V-neck.

ID: 3409270

24. Vertical striped button ups.


Were these supposed to make us look taller or something? The appeal is lost on me now.

ID: 3409779

25. Velcro wallets.

Who needed a leather wallet? This was the perfect place to keep that old condom you carried around.

ID: 3409357

26. Cross Colours.

The fashion equivalent of Skittles.

ID: 3409482

27. Carpenter jeans.


Basically these were just jeans that came with an extra loop on the hip for you to put your hammer in.

ID: 3409323

28. Big Johnson T-shirts.


The T-shirt for bros, before there was even a word for “bros.”

ID: 3410629

29. Mandarin collars.

They should be called “Mandar-outs,” amirite?

ID: 3409626

30. Starter Jackets.

The best thing to wear when you wanted to look like you put on 25 pounds. Also, the jacket was incredibly noisy thanks to the whoosh-whoosh sound you made whenever you moved your arms.

ID: 3409577

31. Rayon shirts.

Columbia Pictures



“I know what guys will like! Silky printed shirts that are made from synthetic fiber! Quick, call the ’90s and tell ‘em we’re coming!” – Person who created these fashion fails.

ID: 3409965

32. Frosted tips.

Dimension Films


Have you seen the awful photos of Justin Timberlake with frosted tips? Yes. Well, the sad truth is that frosted tips looked even worse on you.

ID: 3409931

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