Funny Fashion Fails From the 2000s

Does anyone remember the epic fashion fails of the 2000s? Some are very funny and some I actually love! Here are the funniest fashion moments from the 00s.

Oh the 2000s. How I miss that decade! It certainly felt a lot more carefree in those days and I remember running home to watch TRL and going to see the Backstreet Boys in concert. It is funny to see how much things have changed, and so quickly! Does anyone remember filling their cupboard with tinned food on New Years Even in 1999 and waiting for something to happen? One of my favourite parts of the 2000s is the unique fashion we had back then. As a decade, it was certainly considered to be the most modern era, more so than the 90s, with a lot more freedom and opportunity to express your style, sexuality and choices.

The internet was just beginning to appear in a lot of people’s homes and there was a lot more exposure to the media through our (slow) home computers. Although this article talks about the funniest fashion fails of that time, I actually like some of these outfit choices! Hey, sometimes it is good to stand out and try risque things that people don’t always agree with at first, right? 🙂 Here are some of the funniest fashion fails and memorable fashion moments of the 2000s.

Britney and Justin – Denim on Denim on Denim

The number one fashion fail look of the 2000s has to be Britney and Justin’s 2001 appearance together at the VMAS. Honestly, I remember looking at this as young teen and thinking it was super cool and asking my mom if we could go shopping for more jeans. Of course, it is considered to be a complete fashion faux pas. I thought Britney and Justin looked so in love, and loved their bold statement as a couple. Would you not say that this was a boundary-pushing outfit? Please, take me back to the time that Britney and Justin were still in love! Those were happier times for sure!

Christina Aguilera at the 2002 MTV Video Music Awards

Christina’s dramatic change in style was quite a shock for me. In a way, it kind of signalled the end of my childhood and the beginning of my teenage years. I remember hearing the song Dirrty on the radio and my mom trying to turn it off while I protested. Remember how she wore her underpants over her very low wasted bell-bottom jeans in the music video? That was one trend my mom forbade me to try, and I have to say I do thank her for that! 🙂 One of her most famous looks, which to me is pretty legendary and an outfit that will definitely bring you back is the outfit that she wore to the MTV VMAs in 2002, considered to be an iconic fashion fail. I can’t think of another outfit that manages to be so revealing in so many places, without actually showing anything inappropriate. Yes, this was an outfit my mom definitely forbade me to copy! Here Christina opts to go shirtless and instead use her scarf as a top. Remember our parents asking us why we insisted on wearing skirts that looked like a belt? I think that this skirt can definitely be described as a belt and is certainly something our fathers wouldn’t be caught dead having their daughter wear.

Juicy Couture Velour Tracksuits

One of my favourite fashion moments is most definitely the Juicy Couture tracksuits that anyone who was anyone would wear, in all many different colours. I remember begging my mom for a pair, and although they are casual, they certainly were not cheap. I loved the velvet yet kind of classy-casual vibe this outfit gave. It was seen worn by really famous celebrities including Kim Kardashian, Britney and Paris Hilton. Today, the tracksuit look has definitely returned, however, most of the styles are oversized with a skinny leg, a la Fashion Nova. This is one fashion fail of the 2000s that I would certainly not mind making a comeback! I love the low-waisted, bell-bottomed tracksuit bottoms that enhanced your figure and the cosy velvety tracksuit jacket. It is perfect for those days you want to go shopping and look casual or take a plane ride in ultimate comfort.

Von Dutch

Did you really fall prey to the fashion fails of the 2000s if you never owned an item by Von Dutch? I don’t think you can say that you really lived one of the most important fashion moments of the 2000s if you didn’t! It was definitely important to sport either a T-Shirt, Trucker Hat or Bag with the iconic brand name printed on it. Paris Hilton was definitely a fan. I think the photo below is one of the most 2000s images out there. Check out her crazy Hairdresser Clip hairstyle, Von Dutch T-Shirt, Juicy Couture Tracksuit Bottoms and Flip Phone! This is making me miss those simpler times! Remember when Kelly Rowland texted Nelly via the excel spreadsheet on her Nokia mobile phone in the video Dilemma? They were very funny times indeed!

Ultra Low Waist Jeans

The 2000s were a time when low waist jeans were the only jeans that were acceptable. How funny that now, the opposite: super high waisted jeans are the in trend. I really do feel sorry for my mom looking back, these trends were not her favourite for her teenage daughter to try and copy! Back in the noughties, these jeans were not just simply low waisted. They were ULTRA low waisted, revealing your hips and almost meant that you couldn’t wear underwear. Britney still loves these jeans and has recently been sporting them today. I would say however that the ultra low rise jeans are definitely a fashion fail and should probably stay in the 00s where they belong!

Platform Thongs

Who can forget this trend of the early 2000s. This fashion fail brings back the fondest memories of going down to the park to meet my friends, wearing my ankle bracelet, bell-bottomed jeans and halter neck top. Anyone? Can you argue with the fact that the platform dressed up the slippers in a way? Please don’t judge me, I have only good memories wearing this fashion item! Though I will admit, they were not the easiest shoes to walk around in without falling over a few times, a la Julia Stiles in 10 Things I Hate About You.

Absolutely every fashion moment from Mean Girls

I don’t think anyone can forget the iconic fashion moments in Mean Girls, forever cemented as one of the ultimate girls movies of all time. The fashion moments in there were iconic and fashion fails at the same time. But they were certainly fashion fails that I love. Please don’t hate. Who can forget that on Wednesday’s we wear pink, that you can never wear the same outfit twice, and that you can never wear the same outfit as Regina George? Take notes ladies. And if you were paying attention, you will notice Regina George’s mom wearing a Juicy Couture tracksuit! This movie is definitely 2000s fashion bible gold, and definitely so fetch!

Studded Belts

I don’t mind this wardrobe staple sometimes, as it can look good if you are trying to dress up your regular jeans. These belts came in many different colours and shapes with all kinds of things studded on them, diamante crystals, circular round metallic shapes, to name a few. I think all of us teenage girls had at the very least a black studded belt in their closet, to prove how hardcore we were, of course!

The Best City Walking Shoes That Are Actually Fashionable

Ugg Boots

Ugg Boots were a very popular student trend, they were definitely very comfy and helped you keep warm, especially in those cold winter months. Can you believe that Uggs actually made a lot of appearances on red carpets though? This fashion fail certainly appeared on many celebrity events, paired with the iconic pirate wreck asymmetrical skirt and the fashionable statement hat. I’m sure Beyonce would not be caught dead in Uggs at any major event these days!

Long Dresses Over Jeans

Remember this funny trend? I remember seeing this sported quite often on the red carpet. I have to say, Jessica Alba looks stunning, no matter what she wears! This look actually works for her. It was a favourite style of Britney, who wore a similar number to her Crossroads movie premiere and Kelly Clarkson when she won American Idol. To recreate this look, you would just need to wear a flowy dress over some bell-bottomed jeans. Oh, and don’t forget to ask for blonde streaks when you next visit the hairdressers to complete your look!

Everything from Legally Blonde!

I’m sure any girl into fashion would have loved to have raided Elle Wood’s wardrobe from the 2001 movie Legally Blonde. As we know, Ariana Grande did just that recently! I’m definitely all for girls who are smart and stylish at the same time! The entire movie has several iconic outfits that still creep into fashion today, including the beret style caps, fluffy jackets, coloured lens sunglasses and skirt and jacket sets. Although, the skirt and suit set that Elle dons is so iconic, made completely of pink leather.

Oversized Metallic Louis Vuitton Bag

I don’t think you can get more noughties with this item, as it really evokes the shiny new millennium era we entered in 2000. Kim K, Paris Hilton and Britney are definitely queens of the fashion fails of the decade. I do admit, with all of these looks, I don’t hate them as they remind me of happy times in my teenage years. I personally would love to own a Louis Vuitton bag like this, however, I do understand that they may not have been accepted by serious fashion critics. This photo also reveals the aviator style sunnies, belly button piercings and fancy flip flops…yes, flip flops were worn even at red carpets!

Writing this list has brought back a lot of fond memories! There are definitely a few items that I am going to secretly steal and reincorporate into my wardrobe. I’m thinking that some of the craziest items on this list probably existed due to the excitement of the new millennium. We were definitely trying to be as futuristic, risqué and modern as possible.

What are your thoughts on the above looks and fashion fails? Did you fall prey to any of these looks during the 2000s? Let us know your thoughts in the comments down below!