The '90s Were A Mess: Crushes Who Had Some Questionable Taste in Fashion (20 Posts)

Whether we like it or not, '90s nostalgia is here to stay. Many of us yearn for a time before social media. Those times when we had to wait in order to watch our favourite TV show or film during a specific slot. When we used pagers. When we had crushes on some of the hottest musicians and actors out there (we still pine after you, JTT!).

We had so much fun playing with pogs, watching music videos on MTV, and waiting to record our favourite songs with a cassette tape. These activities kept us so busy that we totally ignored some questionable fashion choices by our favorite stars.

Maybe we even imitated these fashion disasters ourselves thinking that it made us cooler—because, at that time, it did! To remind us of these fashion mishaps, here are some pictures of our '90s crushes. To be honest, we have no regrets!

20 The leather suit

Almost everyone had a crush on one, or even two, of the Hanson brothers. Even those who didn't like their music had respect for this group. These teenagers wrote their own music, defined their own looks, and didn't care what the rest of the music industry was up to. They dressed how they pleased and wrote music from the heart!

Despite this now-dated look, they unknowingly challenged the idea of masculinity by making long hair trendy for guys. They may no longer be as relevant, but we're still thankful for their contributions. They opened the doors to the bubblegum pop genre that dominated the late '90s and early 2000s, and made teenage songwriters relevant. Plus, Zac Hanson was the youngest songwriting Grammy nominee in history.

We still want to know where someone would procure the leather outfit we see Taylor Hanson wearing. In the '90s, we all probably swooned over this look and became depressed when we figured out how much it would cost to even get a leather jacket! The important thing here is that Taylor Hanson and his brothers look happy and carefree. We just wonder if they have this picture on display to remember the time when Hanson dominated the world. Still, you've gotta wonder if they're seriously sweating under that suit...

19 Just... everything we see here

You have to give kudos to NSYNC for having smiles so pretty that you could look past these outfits. We're sure the band was just doing an ode to NASA or something at the time. One up side to this time-capsule is that the band decided to coordinate their outfits. We can imagine the conversation went something like this:

"Shiny outfits aren't just for girls!"

"You're right! We're going to look great."

"And if we go down in history, we go down together!"

Then they probably gave each other high-fives. Joey Fatone probably chose those sunglasses as an ode to Bono from U2. We're betting that you probably went to the nearest mall to find a pair of yellow shades. You probably went out to find a similar patent leather suit, only to realize that you didn't have the $120 to spend on it. So, you probably got a summer job just to buy an outfit you'd wear once.

Or maybe you just danced around to the latest single and ignored the outfits. Because it's not about what you wear, it's about having the guts to wear something like this in public. We'd make remarks about the highlights, but plenty of other places have done the work for us. Besides, they're coming back in style.

18 Those jeans!

Or what's left of them anyways... We still miss TLC's Left Eye and wonder what would've happened to the band if tragedy hadn't struck her. One of the best things about the band was that they weren't afraid to take chances. In a way, this outfit epitomizes the group's level of confidence. It also showed women in the music industry that they didn't have to conform to mainstream fashion trends whatever genre of music they were in.

The outfits in this photo show that we can create our own fashion.

We can be part of a team, and still exude our individuality. That's what a lot of TLC's music was about. And hey, kudos to them for wearing ripped jeans when a lot of people were associating that look with the grunge genre. Just because you're an R&B singer doesn't mean you can't be rock and roll, too. The cut up shirts, bling, and what we're assuming might be some war paint, show us that TLC isn't here to mess around. It wasn't just boy bands that had our hearts, it was also this power group of rad women! Still, we probably wouldn't have had the confidence to wear this.

17 Coordinated outfits

Via VH1

Destiny's Child was known for their legendarily coordinated outfits as well as their music. You'd be lying if you said you still don't listen to some of their tunes (even back when there were four of them). Even back then we knew there was something special about Beyoncé! Those of us who got that vibe aren't surprised by her status as a living legend today.

Here is a feat of unparalleled coordination. It's not to say we wouldn't necessarily wear something like this. We just aren't sure if we'd do it with two of our buddies, because most people go out of their way to make their outfits unique. Also it kind of just looks... dorky. Sorry, Destiny's Child.

An admirable feature of this outfit, though, is the perfectly matching makeup. It's very hard to get women to agree to wear the same shade of lipstick on the same day and on purpose. So, in a way, these outfits scream teamwork! The three shades of orange, turquoise, and silver must have been difficult to agree on. And the Indigenous-inspired look also reminds us of that cringe-worthy time in the '90s when cultural appropriation was acceptable on the red carpet.

16 These shoes were not made for walking


Did anyone else sprain at least one ankle trying to dress up like their favourite Spice Girl? We're glad to know we're not the only ones. Unlike Destiny's Child and others alike, what we respect about the Spice Girls is that they each wore their personalities on their sleeves. They taught us that being a part of a team didn't mean having to lose yourself or your individual fashion sense. Now that many of us have reached an age where we've ceased to care, we probably dress like Sporty Spice as often as we can.

We've also probably figured out that Scary Spice wasn't that scary.

Nor do we bat an eye at meeting someone bold enough to wear her futuristic look! And we'd like to think that we're mature enough to understand why Posh Spice wore that lacy getup. Though it's not as visible to the discerning eye just yet, their makeup was probably frosted. Many who grew up around the era of the Spice Girls is guilty of wearing frosted makeup outside of a costume party. Still, kudos to the Spice Girls for remaining true to themselves and for being more coordinated than we are. Girl power!

15 That time when the Backstreet Boys joined the cast of 'Grease'

The Backstreet Boys were actually guilty of several fashion crimes, but we've since forgiven them because it was probably their stylist's fault. We had some pretty terrible fashion options back in the day. Besides, their smiles and coordinated choreography moved us! This particular look from the '90s actually seems inspired by Danny Zuko in Grease. From an artist's perspective, this choice made sense for BSB. After all, Grease is a musical that relies on talented actors who had the discipline to learn some really complex choreography.

Maybe this was the film they'd watched on their tour bus as they prepared their new dance routines. Who knows?

What is true is that they actually sort of look cool, but the look isn't true to the band. We can't imagine them performing comfortably in this get-up and we're kind of glad that we didn't see them try. You'd need a lot of confidence to try something new. Especially when you know that your new look will be photographed for posterity! Despite this strange fashion choice, we've got to hand it to their hairstylist. Some of us can barely shed bedhead, yet here they are with their perfectly coiffed hairstyles.

14 That power suit, though

Via Pinterest

Joseph Gordon-Levitt is probably one our favourite celebrities to this day. We admire him for always sticking to his guns. He's also never starred in a crappy movie which is really something. and congrats to him for being mature despite the difficulties of being a child-star in Hollywood. Bottom line, Joseph Gordon-Levitt is a decent—nay, perfect—person. Plus, did you know that he's a talented musician, too? Yep! But that doesn't mean he always had the foresight to consider how a picture of him in the '90s would end up here.

However, we like to look at the positive side of every awkward '90s photo.

Instead, we decide to focus on how this gaze exhibits confidence despite not being old enough to drive. Here's what we know: Joe (as he prefers to be called) was playing an alien life-form who was actually pretty old. Somehow, this life-form wound up being trapped in a human teenager's body. That must've taken a lot of discipline and must've been a confidence-booster. He was probably making more than his parents at the time. That would probably make us grimace at the camera like that, too. But man, that power-suit would make Hillary Clinton very proud. That long hair also gave a lot of girls "Hanson" vibes, too. So we've got that at least...

13 The jean dress

Britney Spears has shown us that we can weather our crises with grace and grow up to be responsible adults who are comfortable in our own skin. This outfit proves that Britney has always been a confident powerhouse. A veritable trend-setter, she always had what it took to wear any fashion craze and make the insane look totally normal.

That's what happened here. Now, we're not blaming Britney alone for this questionable decision. Most media outlets tend to show a picture of her and her ex, Justin Timberlake, wearing a similar getup. But as you can see, Justin is already on this list, so we'll quit pestering him.

What this outfit shows us is that there's no scrap of fabric that Britney Spears can't wear well. We do give her kudos for her accessories, and that her hairstyle makes her look like a real-life Barbie. The fact that you can't see her shoes only adds to the enigma that is Britney Spears during her teenage years before she settled into her fame. Regardless of this fashion choice, you can say that it says a lot about who we were in the '90s. Just a bunch of kids who loved jeans and would make anything out of them.

12 This funky get-up

Via Pinterest

If you haven't heard of Jamiroquai, then you're missing out. This acid-jazz group from the UK mixed a wide variety of genres together. In doing so, they created danceable music that still sounds new to this day! Their outfits here reflect how they're influenced by many other cultures, genres, and musical eras. It's pretty obvious that they didn't care about what others thought; their decisions to be unabashedly themselves was probably part of the reason that their careers have lasted to this day.

Look, in the '90s, none of you cared about the consequences of our fashion choices.

We didn't think twice about combining skater styles with Andean sweaters, big sunglasses, and whatever you call that hat on the lead singer's hair. We were all willing to go the extra mile in order to look cool. The choices reflected here also give us two messages. The first is, just because you're good at making music doesn't mean you're a good stylist. The second message is that fame is a double-edged sword. Yes, there are parties, magazine covers, free stuff, and adoring fans everywhere! But there are also evil photographers who will keep your positive and negative choices on record. And the evidence will remain until we invent something better than the Internet.

11 This robot-inspired get-up

Via Pinterest

On the one hand, no teenager has a good fashion sense—ever. We've all probably got awkward pictures similar to Aaron Carter's. And most of our parents had the foresight not to let us walk around in public looking like this. At least not without a warning anyway.

This suit looks like it was made out of a recycled robot! This picture reminds us that we too were once guilty of excessively teasing our hair in order to look cool. I'm sure some of us have used enough hairspray to damage the ozone layer. This outfit is, and was, all of us.

In a way, this strange choice of attire also shows how carefree we were. You're a lot less self-conscious when it takes a trip to the pharmacy and an hour to get your pictures back. When you get them back you think it's great that you have something for your scrapbook. Then you remember that in the '80s people used at least four cans of hairspray and had mullets, so that makes you feel less bad.

Yup. Our logic was sound and infallible back then when we consider that our awkward teen pictures are even less awkward than those in the previous decade. Plus, an awkward picture only makes Aaron Carter more human, and we can dig that.

10 Mom jeans ruled Beverly Hills

With everything we've seen in the 21st Century, we can actually say this look is quite Presidential (let's not forget President Obama's mom jeans). But what can we say? The '90s was a time when we thought Brandon and Dylan looked great in this. We can't help but wonder if this is what the popular kids at our school wore in order to be cool. What did we wear in order to avoid cruel bullies? Selective amnesia can be a blessing!

The cast of the original 90210 may have gone along with their stylist's questionable choices.

However, they can't be blamed for the trends that were made available back then (what were you thinking, designers?!). You can choose to focus on the mom jeans and lack of crop tops. Just remember that such collaborations and coordinated outfits are very rare in Hollywood nowadays. One thing everyone did right was their hair. Sure, these haircuts aren't as trendy as they once were. But who knows? You might see these hairstyles again in about 20 or 30 years from now. Hey, you've got to find the positive of any questionable fashion choice.

9 This pastel outfit

Kirsten Dunst is yet another child star who made it through the difficulty of having her awkward years on blast. There's a lot to respect about that. Plus, she's now known for her awesome film collaborations with Sofia Coppola! Her consistent work with this director has helped her continue her success, and we're sure that she's still got a lot more to give us!

This picture shows us that even the coolest kids in the '90s had their moments of epic strangeness. Our collective style obsessions of this decade are all on display here.

Remember the ubiquitous strappy slip-on dresses, shiny shoes, butterfly clips, and the hairstyles? Man, we thought all of those would make us look as cool as Baby Spice. The good thing about this moment is that Kirsten Dunst was totally feeling it when she took the picture. She definitely had no idea that there was another kid looking directly at the camera, and that makes this picture almost endearing.

Some fashionistas may point at this picture and wag their finger at Dunst while demanding an explanation. But we choose to look at it this way; during the time this picture was taken, Kirsten Dunst was a teen queen and everyone here looks happy. In short: it was what it was.

8 It was once cool to pour a gallon of vaseline in your hair

Via Buzzfeed

If you didn't have a crush on Erik von Detten, then you didn't grow up in the '90s. To live in that time meant that you had to acknowledge that he looked good and also did a lot of cool work. He voiced Sid Phillips in Toy Story 1 and 3, was one of the voices on Recess and later appeared in The Princess Diaries. Yes, it's true that he was often cast as a jerk in his later years. Many of us had a crush on him because we thought we'd be the one to change his ways.

One thing that never changed about him during this era was his hair.

We're not sure exactly how he managed to keep it looking like that for over 10 years. NASA should really take notes on the phenomena displayed in this picture. Several people tried using egg whites, hair gels, baby oil, vaseline, and other products. All to try and nab this look, but to no avail. If you're not some famous celebrity, then looking like you haven't washed your hair in two weeks isn't going to work. Well, it might work if you live near a beach in California. The rest of us weren't so lucky and, as such, this questionable fashion choice looked worse on us.

7 Whoa!

Via Pinterest

The '90s gave us plenty of crushes like Joey Lawrence. Known for his role as Joseph "Joey" Russo on Blossom, we knew that Lawrence could always be counted on for a fun time. Just on a first impression of this photo, we think this vest may have been inspired by Aladdin. 

Thanks to his um, well-defined muscles, Joey Lawrence was able to pull this look off. But let's face it, even the most popular guy in school would've been sent home to change his clothes if he showed up to class wearing this. In the end, there are some things best left to cartoon characters.

It looks like the person who designed this vest had leftover fabric from several ties. Then, they decided to be bold in their choice of contrasting patterns and colours. It weirdly works on Joey Lawrence, whose facial expression is the personification of the following thought: is there a genie in the house? 

Unfortunately, there wasn't one that day, but we have yet another fun memory of the '90s. I suppose it was time when we weren't shy about the way we expressed ourselves through fashion. it was a way for us to express the rebellion brewing inside of us. Or, you know, we just wore outfits without thinking about the consequences.

6 Someone was really inspired after watching The Mask

Via Pinterest

This picture reminds us of a purer time. One where the romance of the coolest weirdos in '90s cinema was going to last forever. Winona Ryder's outfit was cool and is something a lot of people would probably still wear. Her lipstick game was on point and her all-black outfit could be worn at a cocktail party! Or maybe the funeral of someone you respect. Johnny Depp's suit is another matter altogether, though. It reminds us of the yellow suit that Jim Carrey's character wore in The Mask. While it looked great in the film, it's not something we'd wear to a red carpet.

Especially with all of those wrinkles, damn!

We thought Hollywood A-listers had everything, and that includes the money to buy an iron! To his credit, most of us never focused on Johnny Depp's outfits in the '90s. We focused on the fact that we got to see him become a cool actor through all of his collaborations with Tim Burton. You could say that we enabled the behavior that led to this moment. If we know anything about Depp, it's that he probably wouldn't get embarrassed by jokes made about his look. Bet he fired his stylist after this, though.

5 Remember when it was cool to look like you just woke up?

Via Tumblr

We now admire Leonardo DiCaprio for his environmental efforts and for being in Martin Scorsese films that should've earned him an Oscar. He's done so well that we tend to forget that he was also a child star that only got better with age. He was respected by his peers even at a young age; the guy got to work with Robert DeNiro before he was old enough to legally enter a bar!

Unfortunately, his talent didn't make him immune to strange '90s fads. It seems that guys either spiked their hair in a manner that was inspired by porcupines. Or they'd grease their hair so they always looked like they just finished surfing. In this photograph, we see that Leo allowed someone to combine all of the most important hair fads for teenage boys of that decade.

Still, we're glad that this high-contrast black and white picture really accentuated his eyes. It just delivers a picture that makes us want to reach out and comfort him, y'know? In the '90s, we mostly focused on how people made us feel and were too busy trying to make our own hair look spiky. We didn't stop to think that we might regret this fashion choice later in life.

4 We did have some crazy hat trends back then

Via InStyle

Before Sarah Michelle Gellar became our favourite butt-kicking hero, she had a part in All My Children. This meant having to keep up with '90s trends we all wound up imitating in our quest to be as cool as she was. In this case, we can obviously see Sarah Michelle Gellar watched a few episodes of Blossom and took a lot of fashion inspiration from them. Dark brown and wine-coloured makeup was in at the time apparently. Actually, it's sort of making a comeback thanks to some bold lipstick-wearers. So we can't say that this particular choice of makeup is questionable.

This picture takes us back to a time when we'd tweeze out our own eyebrows under an unnatural light.

We would also wear hats that sort of resembled more adorable versions of bowler hats, and felt it was right to put flowers on them. Such hats were probably just precursors to the butterfly clip trend we all fell for. Still, it's kind of cool to see that even Buffy made the choice of picking something that was in style in the blink of an eye. Sadly. such looks never make it to red carpets and runways ever again. She looks adorable, though! Hey, even slayers have a tame day or two.

3 Remember when we owned that one hair-braiding machine?

Via TheKnot

With everything we did to our hair in the '90s in order to stay trendy and stand out from the crowd, it's a miracle we have any left. Clearly Eliza Dushku had that one hair braiding machine. You know, the one that used two strands of your hair instead of three in order to give you an edgy look. Nowadays you can just do it yourself or look up a quick YouTube tutorial that will teach you how to get this look for free! Except you probably won't want to leave the house with this look.

Eliza Dushku also played a troubled slayer on Buffy the Vampire Slayer. She even wound up acting on one of the best cheerleading films of all time, Bring It On. So we can ignore this small fashion misstep because it doesn't define her legacy.

In fact, she went on to do some pretty cool work, appearing in Jay and Silent Bob Strike Back and doing some awesome voice work. We can't really blame her for trying a trend that took almost zero time to put together. Except she probably had someone do it for her, unlike the rest of us ordinary fashion peons.

2 Too many highlights

Via Alloy

No '90s list is complete without including the great Jonathan Taylor Thomas! He was the voice of Simba, our favorite level-headed brother in Home Improvement, and he gave life to Mark Twain's Tom Sawyer. He also committed the grave error of adding highlights to his hair in shades that were a bit on the light side. But hey, he was becoming a teenager. Since we were all becoming teenagers at the same time, we all committed that grave error with him.

The difference is that our mistakes wound up in our family albums and not plastered on the walls of millions of fans.

There's also the matter of wearing a shirt with a trippy pattern. You probably goaded your parents into buying you some shirts with some of the most "interesting" patterns out there, right? If it makes you feel any better, JTT went on to graduate from Harvard and Columbia University! Because as we've all learned from this article so far, one questionable fashion choice doesn't mean that you'll make awful decisions for the rest of your life. Still, we're pretty sure everyone burned their old clothes later on.

1 Ramen hair

Via Tumblr

Okay, earlier today we said we'd spare Justin Timberlake from ending up on this list twice... But this entire look is the #1 questionable fashion choice ever made by one of our former '90s crushes! Before making jokes we must also remember that we would've never let anyone dump on NSYNC. Anyone who was a teenager in the '90s cries whenever someone even mentions this bad fashion choice. Sorry, but nowadays we refuse to give any slack to Justin Timberlake over this. We have to admit that he went too far with this strange look.

Alas, this picture just further proves our point. Apologies to all of the hardcore NSYNC fans who are still out there.

The lovingly knitted turtle-neck sweater clashes with the large earrings, which many an NSYNC fan probably thought made JT look like a bad boy we could change, right? Still, let's not forget to give Justin Timberlake the credit. He had the necessary amount of confidence (perhaps even ignorance) to wear this look and be proud of it. Now that we're old enough to drink, we can look at this picture and give a toast to the confident crazy teens that we were. And one last toast to the ones we had crushes on.

References: Pinterest.co.uk, forevertwentysomethings.com, cutemistake.com, vh1.com, POPSUGAR.com, JustLuxe.com, in.bookmyshow.com, famefocus.com, HelloGiggles.com, Buzzfeed.com, Tumblr.com, InStyle.com, forums.theknot.com, Alloy.com

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