STYLE. GROOMING. INSPIRATION. ADVICE.
INSPIRATION AND ADVICE
IT MIGHT BE 2026, BUT Y2K IS STILL TRENDING
By Ayis Stephen-Diver, 12 January 2026
Picture: Getty
LET'S START WITH THE BASICS
Picture: Getty
Picture: ASOS
What are the essential pieces needed for a good Y2K men’s outfit, you ask? Well, it all starts with a solid foundation. Millennium fashion has a reputation for being OTT – think bedazzled accessories, comically oversized silhouettes and enough bandanas to put the Teenage Mutant Ninja Turtles out of work. To ensure you don’t overdo it, focus on the basics first. This includes a good pair of cargo trousers, a roster of graphic T-shirts and a handful of simple accessories. When it comes to the top, anything varsity is a win – and you can’t go wrong with a beanie and metallic sunglasses. Once these details are nailed, you have free rein to go as vintage or vibrant as you wish.
GET THE LOOK:
ASOS DESIGN knitted leopard graphic skull beanie in neutral, £14
ASOS DESIGN oversized baggy cargo trousers in brown ripstop, £35
JJ Rebel oversized t-shirt with italy front graphic in white, £11
Nike T90 Metallic trainers in silver and red, £99.99
THE CASUAL APPROACH
Picture: Getty
Picture: ASOS
If you’re wondering whether Y2K can work for casual everyday wear, look no further. As mentioned above, focusing on quality pieces will keep you looking smart no matter how relaxed the ensemble. Just look at the evidence: the 00s were led by stylish legends like David Beckham and Pharrell Williams, who made understated sportswear and baggy jeans part of their daily rotation. By combining micro accessories (like glasses and streamlined caps) with loose-fitting layers, even the most casual pieces look thought-out and fashionable.
GET THE LOOK:
ICECREAM varsity bomber jacket in green with leather panels and logo, £325
ASOS DESIGN rimless sunglasses with smoke lens and metal black frame, £16
Reclaimed Vintage oversized longline denim jort in light blue faded wash, £29.99
Von Dutch loves red stitch trucker cap in brown, £45
A Y2K PARTY OUTFIT
Picture: Getty
Picture: ASOS
On the flip side, if Y2K outfits are so well-suited to casual affairs, can they work for nights out or events? The answer is yes. Before the 10s arrived with smartphones and social media, the early 00s were all about high-low fashion. Think T-shirts paired with ties, blazers topping cargos and Timberland boots in place of formal shoes. Red carpets were dotted with street style, and Hollywood’s high-and-mighty brushed shoulders with industry execs dressed in nothing short of loungewear. Thanks to bright colours, bold silhouettes and branded pieces, Y2K is the one trend where anything goes – so have fun in the knowledge that no matter where you’re headed, your look will surely turn heads.
GET THE LOOK:
Timberland premium 6 inch boots in wheat tan nubuck, £190
ASOS DESIGN slouchy oversized blazer in black pinstripe, £65
ASOS DESIGN oversized baggy co-ord jeans in rinse washed black, £35
Reclaimed Vintage unisex 90's librarian blue light glasses, £15.99