If you listen to this writer, the greatest summer song of all time is Mr Jonathan Richman’s “That Summer Feeling”. Released in 1992 by The Modern Lovers man, it has all the hallmarks of a sun-drenched hit. You’ve got the word “summer” in the title for starters, and then there’s the upbeat Beach Boys-influenced riff. Lovely. Where’s my piña colada? And yet, when you listen to the lyrics, you’ll hear a devastating account of false nostalgia, regret and growing old; tales of summers gone by, and how life will never compare. “That summer feeling’s gonna haunt you the rest of your life,” goes the refrain. And, anyway, aren’t these sunny memories just rose-tinted mirages? Were the good times really that good? “Memory comes taunting,” Mr Richman laments. “You pick these things apart, they’re not that appealing.”

Below, the MR PORTER staff have gone down memory lane and chosen their favourite summer music videos and the clothes to go with them. If nothing else, the mostly 1990s-set selection indeed shows that summer songs and the season they embody invoke nostalgia and happiness like nothing else.

Mr Jim Merrett, Chief Sub-Editor

On the face of it, the original video for 2Pac’s first single for Death Row Records has more to do with the film Mad Max Beyond Thunderdome from a decade earlier than the contemporary Los Angeles it claimed to be a love letter to. However, LA is a parched, desert city that has turned escapism into its foremost industry. And the influence of the post-apocalyptic Afrofuturist outfits worn by Messrs Tupac Shakur, George Clinton, Chris Tucker and Dr Dre can perhaps be seen in today’s collections by the likes of LA streetwear brands AMIRI, Rhude and 424.

A second video (how extravagantly 1990s), which accompanies the song’s smoother, less bombastic remix, reveals the first video to be a dream, as well as 2Pac in a natty vest-and-trilby combo and Dr Dre in a silk dressing gown. This version of pool parties, low-riding jeans and leisurewear is perhaps easier to emulate in real life – and is said to be the impetus that sent Compton resident Mr Kendrick Lamar, who as a child witnessed it being filmed, on the path to becoming a rapper himself. However, for me, I can’t shake off the brutal Dr Dre beats (or the eye patch) of the earlier version. “Shake, shake it, baby.”

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Ms Lili G​​​​​öksenin, Senior Editor

I entered my teenage years in the *NSYNC era of music – ie, a golden age – and while I was never a screaming, obsessive fan, I knew these guys would make a lasting cultural impression. That said, the song and music video for “It’s Gonna Be Me” were released in summer 2000 and heralded the beginning of some dark years for men’s fashion. Take, for example, Mr Justin Timberlake’s paint-spattered, oversized denim get-up in one of the scenes in the video… It’s not great. But during their excellent dance breaks, they’re all wearing outfits I feel certain my colleague Mr Ashley Clarke has in his wardrobe today (in particular Mr Chris Kirkpatrick’s gilet ensemble). Would we have said then that early 2000s fashion would be timeless? No. Are we saying it now? No. But this song still hits, and so do these outfits.

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Mr Ashley Clarke, Deputy Editor

In this, our summer of discontent, I’ve personally forgotten what it’s like to dress for any particular occasion. Which is perhaps why, when I was asked which song I’d like to dress like this summer, my mind flashed to Blur’s 1994 hit “Girls & Boys”, and Mr Damon Albarn looking slobbishly handsome in a Fila velour zip-up tracksuit top. The music video was directed by Mr Kevin Godley, who at the time described it as “page three rubbish”. Featuring the band dancing nonchalantly in front of a green screen depicting Club 18-30 package holidays to Magaluf, the whole thing is a kind of Eurotrash fantasy of holiday copulation as seen through a 1990s Britpop lens, all of it generating a kind of sad nostalgia for Thomas Cook holidays that nobody can go on anymore, even if they wanted to. In any case, I want Mr Albarn’s track top. Oh, and that hair.

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Mr Chris Wallace, US Editor

I know, I know, this is technically a Christmas song, but if there is a song that captures my dream summer vibe better than “Player’s Ball”, I haven’t heard it. Give me André 3000’s baseball-style shirt and a drop-top caddy, and “I’m leaning back, my elbow out the window, Coke, rum and indo” (where legal), would definitely fill my body. So, where’s the party?

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Mr Dan Davies, Editorial Director

The Avalanches’ chopped-up, blissed-out brand of electronica provided one of the summer of 2001’s defining soundtracks. “Since I Left You”, the title track from the band’s debut album, is a typically sunny cocktail of random but lovingly sourced samples, expertly blended by Melbourne mixologists Messrs Robbie Chater and Darren Seltmann. In the track’s award-winning video, two miners from a bygone era are drawn from the Stygian, subterranean gloom by the muffled strains of music from above. When they emerge, blinking in the light of a modern dance studio, they’re engulfed by the beauty of what they see and hear: two extremely attractive dancers pirouetting to the soaring melodies of what sounds like a tropical beach party.

The Avalanches, it’s reported, had originally wanted a video featuring involving synchronised swimmers in the pool of an ocean liner, but the idea was rejected by their record company. The imagery of two portly men in soot-encrusted workwear – grandad shirts, braces and heavy boots – stepping into an incongruous dreamscape of light, colour and warmth, feels especially apposite now in an age when so much seems evocative of another, sunnier time and place.

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