No one knew what would happen to fashion when the world turned from the 1990s into the 2000s. Surely the bright colors and grungy flannel of the last decade wouldn’t creep into the new century. The real question was this; were we prepared for the shutter shades, boot cut jeans, and fedoras that followed? Are we ever really prepared for the next big fashion trend? It’s okay to admit now that you wore a trucker hat ten years ago. Looking back on it, though, you probably wouldn’t do it again. You probably wouldn’t follow any of the trends you’re about to rediscover.
Clothing Brands Headlined By Rap Stars
At no time in our history were more rap stars getting into the clothing business than at the turn of the century. Sean “P.Diddy” Combs started the trend with his massively popular Sean John line. After that, every rapper with a hit song to their name wanted in on the business.
Some forgettable ones include Akoo, Nostic, and Vokal. Do you remember their clothing brands? Neither do we, but we promise you they existed. The trend still exists today, it’s just evolved into the Kanye West’s Yeezy brand and other, higher end lines.
Hair Highlights Are A Lowlight
Back in the day, nothing made us swoon more than Justin Timberlake with his streaky hair highlights. These days if you saw anyone with streaks in their like that you wouldn’t be able to swallow your coffee. The look is just bad. There’s no nicer way to say it.
When it was popular though, boy was it everywhere. It was a requirement if you were a member of a popular boy band. Go look back at pictures of N Sync, 98 Degrees, O-Town, and The Backstreet Boys if you don’t believe us.
Tall Tees Down To Your Knees
Tall tees were an essential piece of clothing for any hip hop fan during the early 2000s. The shirts, designed for tall people, became the size of dresses on us normal folks. Hip hop culture demanded you wear them to cover your baggy jeans though, and if they didn’t fall to at least your knees you were doing it wrong.
You also needed to leave the tags and stickers on these shirts to let your cohorts know you had not washed yours yet. Once it found it’s way to the laundry bin it was no longer valuable.
Trucker Hats Became Mainstream
You can thank Ashton Kutcher for this one. The first moment he was caught on camera wearing a Von Dutch trucker hat everyone had to have one. Now we can’t donate them to Goodwill fast enough to pretend we never bought one in the first place.
The classic trucker hat was white in front, black mesh in the back, but if you wanted to get crazy you could get the front neon-colored. You could also personalize the message you wanted to tell the world. It was kind of like Twitter before Twitter existed.
Livestrong Bracelets Were All The Rage
Who knew a little piece of yellow silicone would become one of the biggest fashion statements you could make? When Lance Armstrong released the bracelets to promote cancer awareness and help fund research, the world backed him up by buying Livestrong bracelets by the millions.
For years these bracelets were the cool thing to wear to show the world you cared about healthcare. If you were caught in public without one, you were judged. Today if you wear one people just look at you confused.
Polo Shirts With Popped Collars
Raise your hand if you used to walk around wearing a polo shirt from Lacoste with a popped collar. This was the look of prep school kids and blew up when celebrities like Kanye West showed up on television wearing them.
Of course, this trend wasn’t cheap. Your polo shit had to come with a decent price tag, otherwsie you weren’t allowed to pop your collar…. Or sit with the cool kids at lunch!
Hoodies Under Blazers For Extra Warmth
Proof that you can’t dress down formal wear comes with those who tried by wearing a hoodie under a blazer. The idea was easy: take your favorite hoodie and put it under your formal best. The trend took off after John Legend start doing it, but we wish it never had.
At the time, we can see what was tempting about this fashion statement. Blazers have slowly become a more casual part of American fashion, so this might have been the logical next step. However, take one look and you can see why this craze only lasted for a few years.
Oh God, Bowties
Let’s all choose to forget that bowties became trendy in the early 2000s. Granted, they’re cute on little kids and puppies, but not grown adults. Especially when combined with suspenders. Please stick to the classic belt and tie. Maybe a vest depending how fancy you need to get.
According to our sources, this trend was called “geek chic.” The new generation didn’t know how they wanted to dress, so they chose to look like Steve Urkel. This is one trend we’re happy didn’t make it out alive.
Cardigans Made Your Grandparents Fashionable Again
When was the last time you wore a cardigan sweater? How many times have you decided not to because your grandparents wear them too? In the 2000’s, this was never questioned. All the cool kids wanted to look like their grandparents and old school cardigan sweaters were readily available at thrift stores nationwide.
Cardigans really had their renaissance as hipster culture took over the world. Why buy new clothes at high prices when you shop vintage at Goodwill? Saving so much on cardigans meant we could all spend more money on kale smoothies.
The Digital Watch Revolution
Before watches went entirely out of fashion thanks to smartphones, the hot button ticket was big-faced digital watches. You know that huge Casio G-Shock your dad used to wear? You weren’t cool if you didn’t have one yourself. Now you’re not cool if wear a watch at all.
These modern retro time pieces might have had a bright future ahead of them. They were big and bulky, but not outright ugly. Then Apple introduced the iphone and the entire watch industry had to figure out a way to stay afloat.
Shutter Shades Didn’t Keep The Light Out
Kanye West had no idea the first time he put on a pair of shutter shades that they would become the must-have fashion accessory of the decade. Put on a pair of these, your Livestrong bracelet, and pop the collar on your polo.
No one looked cooler than you. Look back on those photos now and you might regret your decision. What’s important is you’ve learned from your past mistakes and don’t mess with shutter shades anymore. Right?
Throwback Jerseys Are Still Kind Of Fashionable
Clothing company Mitchell and Ness made a big splash in the fashion world when they started selling throwback jerseys. They were, and still are, the perfect way to show your appreciation for your team’s greatest retired players. The trend got so big, the NFL even started playing games in throwback uniforms!
We’ve all seen the Pittsburgh Steelers’ bumblebee uniforms, or the very old school Tampa Bay Buccaneers creamsicle ones. We love how ugly they are, and Mitchell and Ness proved we’ll even pay top dollar to wear something the older generation considers an eyesore.
Are Boot Cut Jeans Still A Thing?
In practice, boot cut jeans serve a very real purpose. If you wear boots, they are the appropriate pair of pants to wear to with them. Your skinny jeans would never survive being draped over the top of your boot.
At the start of the century, boot cut jeans suddenly took over department store racks. We don’t know how quickly they were flying off the shelves, but it must have been enough to keep them relevant. Some brands even tried bring back bell bottoms!
American Apparel Used To Be On Top Of The Mountain
There was a time in the early 2000s that no clothing chain was bigger than Los Angeles based American Apparel. Stores popped up in malls nationwide and teens and young adults needed to get their hands on them, even though they cost an arm and a leg.
Today American Apparel is no longer around. The brand went bankrupt in 2016 and closed up shop. Gildan ended up purchasing the brand, which now runs as a private online store only. It was also forced to fire its founder and CEO.
You can call it emo hair or Justin Bieber hair, either way it was a regrettable decision so many years ago. The style of brushing all of your bangs down and to one side of your face, covering your eyes, never really looked good and we don’t know why anyone did it.
As quickly as this hairstyle came into fashion, it faded away. We would like to thank Justin Bieber himself for doing this by cutting his hair. He now looks more mature and so do you.
Colored Skinny Jeans Are Back To Blue Today
Skinny jeans are just as popular as ever today, but you’ll be hard pressed to find them in various colors in 2019. When they blew up, though, color was all the rage with skinny jeans. Blue was boring, but red or green weren’t. What about yellow? Why yes, thank you!
Colored skinny jeans were the jean of choice for indie rockers and their fans. If you really wanted to show your love for Elliot Smith, you walked into the store and came out with a fresh new pair of hip hugging jeans in your favorite color.
Fedoras Went From Classic To Casual
On the surface there’s nothing wrong with fedoras. They help protect your head from the sun and even keep you warm during the cold months. And few hats look better on bald males! Still, the fad went absolutely crazy in the 2000’s thanks to celebrities like Britney Spears and Jason Mraz.
Without warning, the reputation of the fedora changed. It became the thing to wear if you wanted to present a more relaxed style. It was the perfect hat for going to the beach or camping.
Messenger Bags Evolved Out Of Bike Culture
For years before the 00’s, if you wore a messenger bag, you rode a bike. The two were synonymous with each other. Then they became trendy and Chrome Industries was the bag you had to have. It was sleek and fit everything you needed to get through the day.
For college students, there was no reason to have a backpack when you could have a messenger bag. They fit your books, laptop, notepads, and everything you needed to show up to lecture and take notes.
Wearing Scarves Out Of Season
This one still makes no sense to us. Why would anyone wear a scarf during the summertime? Nothing will make you sweat faster than covering your neck in cloth. Sometimes fashion is more important than personal comfortm, we guess.
The original culprit for this phenomenon are circle scarves. When hipsters learned about them they all needed one. Nothing matches better with your cardigan and shutter shades than a nice circle scarf. Enjoying the New York summer heat?! At the very least you know you look good.
Brands Inspired By Tattoos
Stars on reality shows in the 00’s are responsible for this trend. The most popular brands we remember were Ed Hardy and Affliction. Both companies adorned their clothes with designs inspired by tattoos. The results were less than desirable.
Reality show stars like The Situation (Jersey Shore) couldn’t get enough of them. Thanks to the free advertising the brands blew up. Fun fact, Abercrombie and Fitch actually offered to the pay The Situation to NOT wear their clothes. The company believed the free advertising was doing more damage to their company than good.