Justin Timberlake has become one of the biggest icons in the world. He’s a genuine triple threat, proving to have some impressive acting chops on top of his stellar singing voice and mesmerizing dance skills. He’s also become a great source of impressive style, growing into the suit and finding new ways to look cool with almost no effort. But that didn’t come without some growing pains, as evidenced by some of the outfits he ended up wearing over the course of his career while discovering the kind of look that he could really grow into.
Seriously, some of the things that Timberlake has worn (both during his time with the world-famous boy band, NSYNC, and after he’d become a solo artist) are pretty embarrassing. Some of those bad choices have even reached into the modern day, as evidenced by his camouflage suit jacket at the Super Bowl Halftime Show. And to think, that’s nowhere near the craziest thing he’s tried to make work. He’s tried messing with his hair, wearing unique color schemes, and even mixing and mashing conflicting styles to try and make for something good. To be honest, there were some real fashion failures in there. Timberlake has had enough misfires to make anyone reconsider his status as a style icon. So despite all of his talent, looks, and taste, he’s still proven to be human enough to make some real mistakes. Here are 15 of the craziest wardrobe mistakes that Justin Timberlake has ever made, proving he will never be good enough for Jessica Biel.
15 This All NSYNC All Leather Mess
Say what you will but the boys from NSYNC seemed to enjoy their time in the spotlight together. The five heartthrobs were the epitome of popular in their heyday and usually tried to make good fashion choices. But then again, this was also the late 1990s and early 2000s, so they were bound to commit some crimes against fashion. Whoever thought to deck the five boys out in completely leather outfits like they were the worst Matrix cosplayers in the world needed to be fired. And that’s before considering the racing stripes they all seem to have across their bodies. There’s nothing JT can do about this one, as it’s a group effort towards embarrassment.
14 The Worst Mix & Match Possible
This outfit is all on Justin Timberlake. This picture was taken at a record signing in 2000 and that is Timberlake look when he greeted his scores of adoring fans. It’s not just that it’s a weird mishmash of styles, trying to incorporate a bandanna alongside a turtleneck. That’s still a really bad call, considering that the two are polar opposites in terms of design but that’s not the worst thing. It’s that the color scheme clashes so hard. Sherbet orange is a bold color to bring into an outfit and it is hard for this color not to clash with the rest of the outfit. But wouldn’t you know it, a brown jacket and bandanna do the job pretty well.
13 NSYNC Really Needed Some Help
Look, no one looks especially stylish in this picture. This shot of the boy band on the red carpet is like a time capsule of bad decisions but we’re not here to talk about whatever atrocity led to the creation of Joey Fatone's outfit. No, we’re here to talk about JT and there is plenty to go on about with this getup. Timberlake trying to rock a light blue suit? Okay, that’s not bad. Timberlake sporting baby blue collar and cuffs? Weird and not ideal but it's not the end of the world. But then you get down to his trousers and realize he’s apparently cut up a throw rug, which he has fashioned into pants. The dorky sunglasses help seal the deal and complete the (very bad) outfit.
12 The Denim Suit
A staple of redneck weddings everywhere in the American South, the denim suit is certainly a statement piece. Justin Timberlake was dating Britney Spears back in the day and the two tried to embrace her public image of being a good ol’ southern girl by indulging in this time-honored, trailer trash dream. They absolutely went all out with this getup, with Spears even having a train on her dress for some reason. Timberlake has never looked sillier. He went the extra mile to have parts of the suit appear more faded than others, which shows a very real commitment to this very ugly outfit. On top of all that, and well, also his head, is a straight up denim cowboy hat. It even has a button in the center of it! They look like the worst parents at the little girl beauty pageant, mixing fine jewelry with the corpses of jeans stitched back together.
11 The "Nice Guy" Fedora
There’s something depressing about the current state of the fedora hat in men’s fashion. Over the years, the hat has become synonymous with a certain subset of guys online who tend to use words like “m’lady” and “men’s rights." It is a shame because the fedora can look incredibly stylish when it’s employed right. One of the main problems with it is that it takes a very certain kind of body type and head size to really make it work. And look, we’re not all Jon Hamm, not even Timberlake has the dimensions to make it work, especially when he was younger. The hat is just too big for him and makes him look even younger than he does. The material also looks like he skinned a teddy bear to make it.
10 The Curly Dyed Blonde Hair
This is an article about Justin Timberlake making bad fashion choices so of course, of course, we were going to have to talk about the curls. This was the standard hairstyle that Timberlake rocked through a lot of the early years of his fame, making his curls a mark of that era in pop culture. Let’s be real here, it looks terrible. The bleached hair is ugly but what makes it worse is his natural color popping through at the roots. The sheer level of attention that went into each of those burnt out curls is staggering. It’s not a look that really anyone could pull off and still look respectable.
9 This Graffiti Nightmare
This is the sort of getup that would have made Tim Gunn claw out his eyes. This outfit is just ridiculous. The combination of colors up top, ranging from pink tie-dye to shiny blue, is just distracting. It would have been the worst thing about his outfit if it weren’t for the atrocious-looking pants he decided to put on that morning. The pants are complete with a skull that looks like it was drawn with a sharpie on his knee and a crescent moon right next to his groin. We know that Timberlake knows how to dress, so what made him think wearing this in public was going to work? We’re guessing he lost a bet, to be honest. He looks like Kohls threw up on him.
8 This Shag Suit
At least we’ve moved away from the curls but this picture of NSYNC isn’t exactly a highlight either. Timberlake is featured here in what looks like a shag jacket that is way too long for his form. And that’s before you consider that he’s wearing matching pants to go with it, which can only be the most annoying pants in the world. They just seem so itchy. Timberlake tries to draw your eyes away from all that with his shirt and tie but he really shouldn’t have. Considering the shiny gold shirt he’s got on, he probably should be trying to draw the eye away from all that. At least he can take some solace in knowing he didn't look as ridiculous as Lance Bass.
7 The Leather Everything Look
Justin Timberlake has been a star for almost 20 years and in that time, he’s been able to define his own style. Luckily for everyone, that style went through some evolution over the past two decades and we no longer have to deal with Timberlake trying to make hideous outfits like this still work. He’s decked out in leather everything here. You can practically feel the heat coming off of him and not in a good way. He’s got to be so overheated in that thing. It doesn’t matter how many smiles he gives, songs that he can sing, or however many hands he goes to shake, that’s all we can think of when we see him trying to make three separate sets of leather work on top of one another.
6 Whatever This Weird Outfit Is
There’s really no explanation for … whatever this is. If there is, it probably reads like the scribblings of a madman. There’s just so much going on with this outfit. The shiny bandana is a very weird design choice, especially considering the otherwise patchwork look of his clothes but that’s not all. He’s also got some baggy white sleeves and those fingerless gloves that even Michael Jackson would have thought looked tacky. It is a hodgepodge of looks and designs and none of them work together, despite everything Timberlake is trying. It’s just a mess and one of the craziest things he’s worn in almost two decades of incredibly odd fashion. This one is just that is impressively weird and not well thought out.
5 Snakeskin Shirt
As Timberlake transitioned into a solo career outside of NSYNC, he also started to get a better handle on his look and how he wanted to present himself to the world. But it took some finessing to get to the icon that we see today and that meant going through some trial and error. One of those errors turned out to be this look, where he tried out a high collared red snakeskin shirt during a concert. More than anything, the shirt just looks uncomfortable and static, not having any kind of mobility or flexibility to it. The black leather pants somehow look even more immobile than the rest of him. Rome wasn’t built in a day and Timberlake needed some time to figure out his personal sense of style.
4 He Just Loves The Worst Hats In The World
Seriously, this guy should be legally prohibited from purchasing hats and wearing them out in public. Timberlake has a bad history when it comes to hats, as this article and the past twenty years have proven. He’s been shown trying to wear the kind of hats that anyone else could easily see weren’t going to work. He still tried to give it his all and sadly, that means we have pictures like this one. Justin Timberlake trying to use his perfect smile to distract from the hat that's bigger than the rest of his head. It’s an ugly hat in general, with an unappealing color scheme and lackluster look. Timberlake looks like he is just trying to grit through it and wear the hat for that elderly relative who got it for him for Christmas.
3 The Super Bowl Camo Blazer
The Super Bowl halftime show is usually one of the biggest events of the year in pop music. It’s one of the largest showcases in the entire world for a musician and this year, Justin Timberlake was the performer. His performance was… fine. The internet came together to make fun of his attempts to engage with a teenager and many bemoaned the lack of an NSYNC reunion. But the other thing that people noticed about the performance was the jacket that Timberlake wore during the show. Some joked that he wore a camouflage suit jacket to blend into his surroundings and avoid all the controversy that came with the initial proposal to pair him with a hologram of Prince. However, the jacket finally made him seem his age. Bad call, JT.
2 His Tacky Cornrows
Cornrows are a traditional African-American hairstyle that has remained strong in the face of modern culture. White Americans have been known to appropriate black culture over the years. White people trying to sport cornrows is never a good look. However, for some reason, in the early 2000’s, this trend became increasingly prevalent. Timberlake became part of the problem when he tried to rock cornrows. Combined with the red shades, he looked like the star of a terrible version of Dracula 2000 or more likely, one of the random vampires that Blade would end up killing inside the techno clubs. Luckily for everyone involved, Timberlake ended up shifting away from that look and has since transitioned into a less offensive look.
1 This Turtle Neck & Cowboy Combo
We know we’ve been harping a bit on the sheer number of ridiculous outfits Timberlake ended up trying to pull off during his time with NSYNC but that doesn’t change make any of these outfits less silly. Take this outfit, for example. Timberlake is clearly trying to make it work for him but there’s just nothing to be done. He's attempted to combine a sleek white turtleneck and also leather cowboy pants. The colors in the pants totally clash, let alone paired with the top. The sheriff star belt just makes it worse. Plus, the sweater is so sheer that you can see his undershirt, thus, defeating the purpose of a sweater.