6 Times Justin Bieber's Street Style Had Us Scratching Our Heads

There was a time when Justin Bieber was a trendsetter among tweens everywhere — remember the famous shag haircut that had youngsters growing out their Y2K spikes? When Bieber broke into the music scene, he was a fresh-faced teen with a preppy but sporty boy-next-door fashion taste. However, over the years, his street style has evolved into something we can't even put into a category.

One would think that after marrying Hailey Bieber, who never steps out looking less than polished, Justin would amp up his style game. However, his everyday looks have only gone downhill, but he's unconcerned with the public scrutiny. "He is fearless. I've worked with Justin Bieber for a decade. It's been the most formative relationship creatively that I've ever had," his stylist Karla Welch told E! News. "There were those horrible 'Worst Dressed' lists, and you never wanted to land on them, but Justin didn't care," she added. It does seem as if Justin is trolling the masses with his street-style 'fits, as they range from the just-rolled-out-of-bed aesthetic to downright bizarre at times.

In August 2023, Justin Bieber accompanied Hailey Bieber to her Rhode beauty event with Krispy Kreme in New York City to launch her Strawberry Glazed lip treatment. While Hailey was on theme with a bright red dress, strappy heels, and adorable strawberry earrings, Justin trailed behind her in a gray hoodie with a pink cap over his head, sweat shorts, and yellow crocs. The head to his hoodie was tied bizarrely around his face in a knot, with the zipper halfway down to his chest. We admit that it was nice that he came to support his wife, but Justin was dressed like he was playing video games in the basement and told at the last minute that he had to go to an event.

In an interview with GQ, Hailey addressed her and Justin's mismatched style and revealed that he often gets ready before her. "He may want to wear baggy sweats to dinner, and I might want to wear a tiny little dress just because that's how I'm feeling. We can't sit there and be like, 'So I'm going to wear this, and you're going to wear this,'" she reasoned. Her friend Kelia Moniz shared, "It's like, it wasn't Justin's day. It was Hailey's day. He's there to support his wife, period. But also, he still looks cool, so you can't hate the guy."

Justin Bieber's style is to wear everything five sizes larger than he needs, but that can be a problem if he's wearing sweatpants that are not secured at the waist, as seen here. While the "Never Say Never" singer was out and about in Los Angeles with a friend, he was spotted wearing a black leather jacket over a hoodie and sweatpants that were practically down to his knees. We know that the '90s style has been back for a while, but we draw the line at the underwear peekaboo trend making its way around again. What's more peculiar about Justin's outfit were his fuzzy Louis Vuitton slippers that were more suited to lounging around at home.

In 2019, Bieber shared a selfie of himself wearing drawstring pants tied super low, showing off his Calvin Klein undies. His striped button-down shirt was open in the front, displaying his many tattoos. "My style is impeccable," he captioned. A fan replied, "Bruh. You look like a gas attendant." Fashion is in the eye of the beholder, we guess.

The US Open is the place for celebrities to be seen, casually showing fans how rich they are with their VIP seats. It's the perfect time to amp up your quiet luxury fashion, but Justin Bieber opted for a super strange getup for the 2023 championships in Queens, New York. We give him points for matching with Hailey Bieber in a black leather jacket, but his choice of accessories was just odd. Justin watched the match through pink bubble Loewe sunglasses and sported a black and white polka dot baseball cap. He worse baggy jeans per usual, while Hailey opted for a simple white dress.

Despite his oversized sunglasses, tennis player Coco Gauff recognized Bieber and used him as an inspiration to win. "I definitely saw who was there. I thought, 'I cannot lose in front of Justin Bieber.' I didn't lose a game after I saw that," she shared with Fox News. "I was definitely star-struck with Justin. 'Never Say Never' was ... one of my favorite songs when I was a kid. Then, 'Baby, Oh, Baby.' I could go through all his songs. Then Hailey, too, coming. I guess it was a little date night for them, which was really cool," Gauff added. If Bieber was trying to be incognito with those pink sunglasses, it definitely didn't work.

Justin Bieber loves to dress for comfort and probably has a closet full of hoodies. However, someone failed to tell him that it's common practice to put both arms through the sleeves. Instead, Bieber carried his iced coffee through the bottom of his sweatshirt while letting the other sleeve dangle by his side, making it look like he had three arms. There are so many questions to be asked with this look. How will he drink his coffee? Is driving even possible? What is wrong with the left sleeve?

As reported by the Mirror, Bieber tried to make the one-armed shirt a thing back in 2015. The "Favorite Girl" singer was spotted skateboarding in New York City wearing a white shirt with one of his tattooed arms completely out of the sleeve. He had on his beloved Calvin Klein undies peeking out of a pair of ripped jeans, not as baggy as his present-day wear. If you see this trend starting to take off, you know where it originated.

Justin Bieber's street style often looks like he randomly pulled pieces out of his closet in the dark and then just put them on without looking at them. While walking the streets with Hailey Bieber, he donned a bright pink knit hat, a slate gray sweatshirt with a light blue frayed shacket, and enormous jeans that were so long that they covered his shoes. We know the baggy look is in, but that couldn't have been sanitary.

At least Bieber was promoting his clothing line Drew House, which he launched in 2019 with its co-creator Ryan Good. The denim that Bieber was sporting on his walk is the wide-leg jean vintage color block, which retails for $175, per the brand's website. If you want to copy Bieber's style and get a pair, just be sure to get them hemmed so you're not walking all over them like the pop star.

Was Justin Bieber cold, or did he literally roll himself out of bed to go on a date with Hailey Bieber? Either way, the singer once dressed bizarrely — even for him — in a pair of colorful quilted pants and a large multi-colored crochet blanket draped over his shoulders. Justin topped off the look with a plaid bucket hat from his clothing line, Drew House. Perhaps he was just in a rainbow-inspired mood, as even his sneakers sported multiple colors.

This wasn't the first time Justin wore bed linen as outerwear. In March 2023, he was spotted avoiding the red carpet and sneaking into the Vanity Fair Oscars party wearing another crochet blanket, this time with large floral designs, per Page Six. Although Hailey chose to pose outside for the photographers, it looks like her husband wasn't camera-ready at all. Good thing he was on the list or he might have been turned away with his unbothered 'fit.