In that quintessentially 1990s film Clueless, the lead character, Cher Horowitz, delivers a blistering critique that, at the time, felt spot on: “I don’t want to be a traitor to my generation and all, but I don’t get how guys dress today.” But, in the decades since its release, our view of the getups worn by the chaps in the film – their baggy cargo trousers, tie-dye T-shirts and ill-fitting baseball caps – has changed. What once seemed slovenly now seems cool. It might be heresy to say so, but Cher is distinctly out of fashion on this.

The 1990s-style trend has for some time been back in a big way. Cargo shorts, gold-plated chains and anything with a logo has become high fashion. Perhaps it’s wistfulness for a time when things seemed be getting better and kinder, or it might just be that fashion editors have been overcome by nostalgia for their youth. Whatever the reason, the trend is here to stay.

So, if you’ve recently found yourself contemplating whether you can pull off a bucket hat, you’ll want to read on for our list of the men who stylishly conquered the 1990s, and the lessons we can learn from them.

Mr Kurt Cobain is hardly an unsung hero of 1990s style – treatises have been written on the Nirvana frontman’s expansive collection of flannel shirts alone. But we want to bring your attention to the other great sartorial love of Mr Cobain’s life: the fuzzy cardigan. It’s an improbably stylish garment, to be sure, but a true grunge icon, immortalised both by Mr Cobain onstage and by Mr Marc Jacobs in his Seattle-inspired 1992 Perry Ellis collection. According to The Guardian, the dishevelled and distressed garment above (spun from acrylic, mohair and Lycra-blend yarns, in case you were wondering), which made an appearance at an MTV Unplugged session, fetched $137,500 under the hammer just a few years ago. The takeaway? Come as you are or clad in a fluffy, oversized cashmere cardie from The Elder Statesman or AMIRI – the LA labels do fine lines that are slightly more affordable than a trip to Christie’s or Sotheby’s.

The 1995 film La Haine, provides a 24-hour snapshot of a Paris banlieue after a riot. Intrinsic to the creation of mood and evocation of the time and place are the clothes the actors wear. The movie has style in spades. (It helps, of course, that writer and director Mr Mathieu Kassovitz shot the entire film in a moody greyscale.) Mr Vincent Cassel looks cool in a tracksuit. His friend Mr Saïd Taghmaoui’s mismatched shearling-jacket-and-sweats ensemble is nonchalant, assured and oh-so-very French. The only thing missing from this still, above, is the circling plumes of cigarette smoke issuing from a freshly-lit Gitanes. No wonder streetwear devotees are all trying this at home. And you can, too – purists should head to adidas Originals or Nike for their sportswear fix this season, while luxury brands such as Gucci, Needles and Prada offer a more streetwise approach.

Playing second fiddle to the Fresh Prince is no easy feat, but Mr Alfonso Ribeiro assumed the role of cousin Carlton Banks with, well, not grace exactly, but certainly charm. It’s usually Mr Will Smith who’s awarded accolades for his 1990s style, but, in this case, a logo hoodie and cap is no match for the surfeit of prep happening to his left. Layering a cricket-inspired sweater vest over a Madras plaid shirt definitely belongs to the so-wrong-it’s-right school of 1990s dressing, and therein lies the genius. You don’t get a namesake dance by playing it safe, after all. Thus, a Wasp-ish wardrobe of chinos, polo shirts and a whole lot of bow ties is certainly a look. Make like Carlton and spend your big bucks at Polo Ralph Lauren – the born-in-the-US brand mastered the art of prep long ago, but they’ve really cranked things up a notch in recent seasons.

Balenciaga only recently started offering sunglasses, which is why we can confidently say that this press shot of a trio of Wu-Tang Clan members visiting London was definitely taken in the 1990s – 1994, to be precise. Which means that U-God, GZA and Method Man et al, were fresh from releasing their debut album Enter The Wu-Tang (36 Chambers), which, along with heralding the East Coast rap renaissance, ushered in a whole decade of style wisdom. As well as the retro oval frames, take particular note here of the printed bandana, snapback caps, white sports socks and… is that the heel of an OG Nike Air Jordan III we spy? All of which – bar the Jordans, of course – crop up in the likes of Palm Angels, Fear of God and Off-White’s most recent collections.

*NSYNC were hardly poster boys for cutting-edge style back in the day, unless you were a shrieking preteen, of course. But, look again and their eclectic pick-n-mix approach is the new gold standard. Just peruse at any Vetements collection for the proof. Showcasing a smorgasbord of micro-trends here – JT’s oversized football jersey, JC’s double denim, Mr Joey Fatone’s tagged skate tee, the nylon windbreaker on Mr Lance Bass and bluer-than-blue jeans for everyone – there’s no shortage of inspiration to go around. One final word: don’t worry, the bleached tips are entirely optional.

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