Guys of a certain age (this writer included) look back on the turn of the millennium with rose-tinted visor sunglasses. It was a time of simple, youthful rebellion – of Tony Hawk's Pro Skater, angsty nu metal and the WWF's Attitude era, and in keeping with this zero-care mentality, from a fashion sense, it was a time where low-effort comfort dressing became the new cool. Now, two decades later, men are starting to catch up with the girls in embracing the overall look of the early 2000s, trading glitter tops and low-rise jeans for party shirts and vintage band tees. And there are plenty of Y2K-inspired menswear trends to jump on while the going's good.
Sport-inspired sunnies

Sport-inspired sunnies
Call them speed dealers, call them visor shades, call them whatever you like – petrol station-chic shades have transcended the crowd who used to wear them ironically at festivals, and reclaimed their place in the fashion mainstream. This is partly thanks to high fashion revivals from brands like Balenciaga, but more accessible brands like SZADE, Oakley and Nike are leaning into the trend in a big way.
Loose tailoring
Before Mad Men and Daniel Craig's 007 came along to usher guys into a more refined era of razor-sharp suiting, baggy suits – a trend carried over from the NBA stars and boy bands of the 90s – were all the rage. Now, we're seeing red carpets being taken over with a new wave of relaxed jackets and trousers – a reflection of the relaxed approach to formalwear that seems to have taken root at awards ceremonies and film festivals the world over.
Baggy everything

Baggy everything
Skinny jeans and slim-fit t-shirts have seemingly had their day in the sun for now, with guys instead favouring skatewear and workwear that swathed an entire generation of rap metal-loving skate punks at the turn of the millennium. Think boxy tees, baggy jeans, straight fit painter pants and loose layering pieces.
Double denim
Remember that pic of JT and Britney draped in their best Canadian tuxedos at the 2001 AMAs? This is the energy we're channelling in 2023. In fact, pretty much any type of high-octane denim, whether it's patchy, torn, faded or multiple shades worn at once, is in, thanks to the iconic Y2K brands like Diesel, Helmut Lang and Versace Jeans roaring back into relevance.