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STYLE AND CULTURE
JUSTIN BIEBER CAN’T STOP WEARING OVERSIZED STREETWEAR
By Ayis Stephen-Diver, 31 March 2025
Justin Bieber’s transition from purple-loving teenager to the millennial Adam Sandler has been fascinating to watch. He’s either filling up his tank in sweats + tees three sizes too big or on a date comically mismatched with his wife Hailey – an evolution we can thank his long-time stylist Karla Welch, and more recently Jenna Tyson, for. But if you look closer, there’s always a method to his madness, whether it’s the fresh-off-the-runway pieces or a barely there detail that pulls the ‘fit together. Here are four ways to emulate his now-signature, dressed-down look for the new season.

Picture: Getty

Picture: Getty
#1: WITH BOXY HOODIES
Considering the number of times we’ve seen him in them, it’s obvious that Justin's favourite garment is the hoodie. We can’t blame him – it's a throw-on-and-head-out piece – especially the boxy, ultra-baggy variant he’s known for. A high-low approach to styling is the JB way – think jeans or smart trousers.
GET THE LOOK:
Similar: ASOS DESIGN bonded leather woven belt in brown, £18
Similar: ADPT oversized acid wash hoodie in beige, £32
Similar: ASOS DESIGN baggy trousers with workwear patch in stone, £35
Similar: ASOS DESIGN slipper boots in brown faux fur, £25

Picture: Getty
#2: THE NEW PREP
His fashion philosophy isn’t restricted to modern streetwear either. Traditionally preppy pieces like button-up shirts, shorts and even Mary-Janes can get JB-ified too. Judging by the clashing orange sunnies and backwards cap, mixing aesthetics is his thing.
GET THE LOOK:
Similar: Dr Denim Madi relaxed fit resort shirt in butter yellow embroidery, £50
Similar: Bershka baggy denim short in mid blue, £29.99
Similar: Vans Felix sunglasses in white/mirror, £16
Similar: Dr Martens 1461 bex 3-eye shoes in black smooth leather, £160

Picture: Getty

Picture: Getty
#3: GO BACK TO BLACK
Leather jackets, denim jackets, trucker jackets, jacket/hoodie hybrids… You name it, JB has it in black. Although (fingers crossed) you’re not going to need one any time soon, keep a few in rotation for times when dressing up is mandatory – plus some chunky boots and artful layering.
GET THE LOOK:
Similar: ASOS DESIGN faux leather borg lined worker jacket in black, £70
Similar: Lacoste trucker jacket in black, £210
Similar: ASOS DESIGN essential 2 pack oversized t-shirt in white, £18
Similar: Reclaimed Vintage unisex check print co-ord, from £39.99

Picture: Getty
#4: HATS ON
Justin’s hat collection can only be compared to the Gallagher brothers' sunglasses or Jacob Elordi’s bags – in other words, it’s *vast*. And he's not wearing them so he can go incognito either. Sometimes, the best way to take an outfit to the next level is with a statement hat. Icons from New Era, The North Face and ASOS DESIGN are your go-tos.
GET THE LOOK:
Similar: The North Face 66 Brimmer bucket hat in stone, £32
Similar: New Era NY Yankees 9twenty cap in green, £25
Similar: AllSaints merino wool fisherman beanie in black, £45