For a feverish follower of vintage tennis Instagram accounts, picking a single stand-out menswear moment is like asking a film critic to pick their favourite movie. There’s a vast canon of impeccable on-court style that runs from Mr Björn Borg in slim-fit Fila to Mr Yannick Noah in a Mr David Bowie practice T-shirt. And that’s before you even get to the men who became brands in themselves: Messrs René Lacoste, Fred Perry and Stan Smith.

If there is one look that changed the course of tennis style more than any other, though, it has to be Mr Andre Agassi’s first Nike Challenge Court collection, which he debuted at the 1990 US Open as he blasted his way to the final. With his explosive game, rebellious attitude and long, bleached hair (which anyone who’s read his gripping autobiography will know was a wig), Agassi was the perfect moving billboard on which Nike could launch not only a whole new look, but a whole new concept: rock ’n’ roll tennis. Through provocatively bad-boy slogan adverts created with the agency Wieden+Kennedy, Nike was on a mission to rip tennis away from its genteel roots and Agassi was its superstar face.

The Challenge Court kit jumped out of TV screens and practically instructed tennis fans to go and buy the head-to-toe look. There was an immediate style sea change at junior tennis tournaments around the world. Almost everybody wanted to look like Agassi. This kit helped establish the American Nike as the dominant fashion force in the game, eclipsing European sportswear brands in the cool stakes.

The collection included acid-wash denim shorts, tight cycling under-shorts and basketball-inspired high-tops and across all of it there was exuberant use of neon. Ever since Agassi was emblazoned with Nike’s signature Volt yellow (and later with its bright Lava pink), neon has been used by players to signal presence, confidence and aggressive intent. Its greatest proponent in recent years has been Mr Rafael Nadal, who glories in wearing hot pink, high-vis orange or luminous yellow in the face of gentlemanly Mr Roger Federer and monkish Mr Novak Djokovic.

The year after its Flushing Meadows debut, Agassi’s new look put him on a collision course with the All England Lawn Tennis Club. In the weeks running up to the 1991 Wimbledon championship, he had consistently been wearing his loud outfits and the British tabloids were aghast that he might defy the tournament’s all-white dress code. No doubt encouraged by Nike, which was getting masses of free publicity, Agassi refused to rule it out, but when he did finally emerge onto the SW19 grass, he stepped out in the all-white version. The media teasing was a stroke of genius that drew greater attention to the underlying design details and created an even greater buzz around the more exclusive bleached-out colourway.

At last year’s US Open, Nike celebrated 30 years of that first legendary, colourful Challenge Court collection with new versions of the kit, but even bright new stars such as Messrs Andrey Rublev, Denis Shapovalov and Taylor Fritz couldn’t quite capture the original spirit. It served as a reminder that style is largely about a time and a place, but mostly it’s about the man.