Justin Timberlake's biggest fashion blunders

When you have spent more than half your life in the public eye, like Justin Timberlake, your past will always come back to haunt you. Let's take a look at the best of the worst photos of Timberlake over the years.

This old picture of Justin really shows just how far the performer has come style wise. What was he thinking with that plaid shirt?!

Whoever styled this look had very questionable taste! That orange turtleneck sweater, the leather blazer, and a brown bandana...why Justin? Why?

We haven't got anything against tie-dye - it can be a cool look. But this outfit is just too much!

This photo from 2001 depicts Justin standing next to a wax sculpture of himself at Madame Tussauds in New York. By the look on Justin's face, we know we will have fun looking through his photos from over the years.

In 2001 Justin and Britney Spears were the music industry's power couple, and somehow, somebody convinced them that it would be a great idea to show up to an event in matching all-denim outfits.
Who? How? Why?! Perhaps we will never know what led to this fashion disaster, but this photo will never be forgotten!

The Denim Look may have been more Justin's style than Britney's, as he returned to it with his buddies from NSYNC (JC Chasez and Chris Kirkpatrick) at the Annual Blockbuster Entertainment Awards in 2001.

At the 2002 Grammy Awards, it appeared that NSYNC had just one goal: to be the group with the shiniest outfits. They pulled it off, even if they took the idea a little too far. What we find confusing about this photo is Timberlake's outfit of choice: he doesn't match his fellow band members at all!

A hair dye disaster can happen to anyone, even the stars! You head to the store to buy your dye, but you just can't remember which is your color. You aren't sure if last time you bought 'Golden Blonde,' 'Creamy Blonde', or 'Harvest Gold.' You decide to go for 'Harvest Gold,' you go home and dye your hair, only to discover an old box of dye and realize your color is actually 'Golden Blonde'! It's too late, there's nothing to be done, and you have to pose on the red carpet with this hairdo.

Style-wise the '90s were amazing, and many popular trends from that decade have made a comeback. However, the 2000s were a little rougher at times style-wise and brought some cringe-worthy trends. In this picture, we see that Justin Timberlake fell victim to the fad of wearing diamond studs on multicolored leather pants, which makes it hard to imagine that one day he would become a fashion icon.

Everyone warned Timberlake: "If you win an MTV VMA, don't let it go to your head!" It was unavoidable, Justin's first solo album was a huge success, and he won three awards. He was only 22 years-old at the time, so we can forgive him for letting the fame go to his head!

Sticking your tongue out for a photo isn't usually a great idea, but in this case, it could go either way. Some might look at the pic and think, "Oh! How attractive!" while others just see a big old tongue sticking out. We aren't fans of the "tongue out" look, no matter how hot Timberlake is!

The super-low pants look, with your underwear hanging out, was all the rage at the end of the '90s and beginning of the 2000s. We are thankful those days are over! It ruined so many looks for so many people, Justin included. At the 2002 Teen Choice Awards, from the waist up, Timberlake looked great, from the waist down...what a disaster!

This photo may show Justin Timberlake in an awkward pose, but in reality, he wasn't doing anything strange; he was just caught in action while dancing. Timberlake is a fantastic dancer, which makes the average dude, whose only move is the "running-man" jealous. So we couldn't help but take the opportunity to poke fun at the performer to make ourselves feel better about our less than stellar dancing abilities. Sadly, it didn't work.

We can respect Justin Timberlake for his effort to attend the Billboard Awards while injured, shortly after having had an accident. However, showing up at the event accompanied by two sensual nurses has us less than impressed. Luckily, this was way back in 2002, and things have changed a lot for the better.

Wearing sunglasses at night is always suspicious. The smile on Timberlake's face combined with his sunglasses makes us think he was having a pretty good time partying just before this photo was taken. On top of it, the way his friends Lance Bass and Joey Fatone are looking at him doesn't help his case.

We have to admit, Britney and Justin made a cute couple. They were beautiful, in love, and enjoying life. Their style at the time was definitely questionable. However, since it was the beginning of the 2000s, we can forgive them; it was a rough time for fashion. Also, did you know that it is rumored that Justin's hit 'Cry me a river' was written about his break-up with Britney?

We won't even go into why everyone in this photo is looking in a different direction. However, we can't NOT comment on Justin's impossible outfit. Remember, nowadays, Justin is considered one of the best-dressed men worldwide. We choose to see it as a sign of hope: no matter how terrible your style is, there is always hope you too could be a fashion icon!

Whenever Justin Timberlake has spent time in Las Vegas, his style choices have been questionable. That shiny shirt is one thing, but the belt buckle is just unforgivable. There are wrestling championship belts that are smaller and more subtle than the one Justin is wearing here!

Luckily for Justin Timberlake, when he left NSYNC and went solo, his style drastically improved. No matter what we see him in now, he is always impeccably dressed. So much so, his style is copied by people worldwide, and he has become a fashion reference.

Finally, to show how far Justin Timberlake has come, we must admire him in one of his signature looks: the three-piece suit. This outfit has become part of his identity and he totally rocks this look. Congratulations on overcoming your fashion blunders Justin!