10 Style lessons from iconic album sleeves

Posted by
Chris Sayer

Next time you're about to hurl every item in your wardrobe out onto the floor in a fit of "I don’t know what to wear!” rage that’ll probably end in tears (again), just stop, put on some music and relax. Help is at hand. 

If you’ve dropped the needle on any one of these ten iconic albums, not only are you in for an aural delight, but you may have just stumbled across a timeless and important style lesson that'll help you dress brilliantly.

Behold, the influential album sleeves that we think can teach us all to dress slightly better…

Related: 33 Things all great men should own


  • 10 Style lessons from iconic album sleeves

    Bob Dylan – Freewheelin’ (1963)

    Who: Reclusive songwriter, who just so happens to be one of the most influential musicians of the 20th century.

    The lesson: Straight-cut jeans make the cornerstone of any man’s wardrobe. A beautiful woman on your arm comes a close second.

    Garment to buy: Levi’s 501 Original Fit Jeans (£80,

    Album track you’ll recognise: Blowin’ In The Wind

  • 10 Style lessons from iconic album sleeves 1

    Bruce Springsteen – Darkness On The Edge Of Town (1978)

    Who: ‘The Boss’, now 66 years old, is perhaps the most famous living American singer/songwriter with 20 Grammys on his mantelpiece.

    The lesson: Dunno what to wear today? Well, do you have a black leather jacket and a plain white tee? There, that’s what you’re wearing today. A timeless style as cool then as it is now, and one that’ll never go out of fashion. Ever.

    Garment to buy: Schott NYC 50’s Perfecto Leather Jacket ($850,

    Album track you’ll recognise: Badlands

  • 10 Style lessons from iconic album sleeves 2

    DJ Shadow – Entroducing… (1996)

    Who: Josh Davis, AKA DJ Shadow, a legendary producer and DJ that become world-renowned for his genius sampling. 

    The lesson: The nineties are back in fashion, and you won’t get a better snapshot of the decade’s style than this baggy, oversized snapshot taken inside Rare Records in Sacramento, California.

    Garment to buy: An XL Champion crewneck sweatshirt (£85,

    Album track you’ll recognise: Midnight In A Perfect World

  • 10 Style lessons from iconic album sleeves 3

    Tyler, The Creator – Wolf (2013)

    Who: Hyperactive 25-year-old rap star and co-founder of the Odd Future Crew.

    The lesson: There's absolutely no need to be snooty and serious about your style. If you think you can pull of a short-sleeve shirt with cats on it, then you go pull that shirt off. If anyone looks at you funny, it means they’re too square to be hip.

    Garment to buy: ASOS Watermelon Print Shirt (£22,

    Album track you’ll recognise: Domo23

  • 10 Style lessons from iconic album sleeves 4

    Beastie Boys – Check Your Head (1992)

    Who – Hip-hop mavericks from New York City with an unrelenting yet endearing strain of smartassery running through their 35-year history.

    The lesson – Every man needs a ‘classic’ pair of Adidas trainers. From Campuses (as seen on this cover) to Superstars and Stan Smiths, Ad Rock, Mike D and MCA rocked them all, and damn, they still look just as fresh today.

    Garment to buy: Adidas Originals Campus 80s (£95,

    Album track you’ll recognise: Pass The Mic

  • 10 Style lessons from iconic album sleeves 5

    AC/DC – Highway To Hell (1979)

    Who: Hard-rocking Aussies with more recognisable riffs than you can shake a flaming Gibson SG at.

    The lesson: Long hair is back, baby. When ShortList’s fashion director Adrian Clarke reported back from the European catwalks earlier this year, one of the standout trends he talked of was the out-grown, unkempt, choppy hair with heavy fringes that donned the lids of pretty much every model there.

    Garment Tool to buy: Kent Slim Jim Comb (£8,

    Album track you’ll recognise: Highway To Hell

  • 10 Style lessons from iconic album sleeves 6

    Wiz Khalifa – O.N.I.F.C (2012)

    Who: A Kanye-bating, weed-loving hip hopper who broke into the big time with his track Black And Yellow back in 2011, and is the first artist to get more than a billion YouTube views for a hip-hop song with See You Again.

    The lesson: Don’t be afraid of fur. Not a full-blown all-out jacket of the stuff (unless you’re a hip-hop hero like ol’ Wiz here, who can totally pull it off), but a little around your collar. Shearling was the biggest trend of the winter, and a shearling jacket was the season’s must-have. There's still time to wear one now.

    Garment to buy: J Crew Wallace & Barnes Faux Shearling Bomber (£370,

    Album track you’ll recognise: Remember You (feat. The Weeknd)

  • 10 Style lessons from iconic album sleeves 7

    Patti Smith – Horses (1975)

    Who: A true influencer of the New York City punk movement, as well as an inspiration to Madonna, Michael Stipe from REM, Shirley Manson from Garbage and Courtney Love from Hole.

    The lesson:  You’re going to be borrowing your girlfriend’s clothes real soon. No, not her pencil skirts and croptops, thankfully, but major brands like Whistles are fully buying into androgynous clothing right now. Oh, and did you see Jaden Smith recently repping Louis Vuitton’s womenswear line in their spring campaign? Yep, gender-neutral is a big thing now. You and your prettier half both wear the same Breton stripe tees, Vans shoes and backpacks, so it’s logical, right?

    Garment to buy: Armor-Lux 1525 Long Sleeve Loctudy Tee (£49,

  • 10 Style lessons from iconic album sleeves 8

    N.W.A And The Posse (1987)

    Who: Seminal hip-hop group featuring rap pioneers Dr. Dre, Eazy-E, Ice Cube and more.

    The lesson: The easy thing to do here would’ve been to choose Straight Outta Compton, not only the group’s most famous release but without doubt one of the most important rap albums ever. Instead, we’ve opted to go down the route of this Macola Records compilation filled with Dre-produced tracks, mostly because of all that INCREDIBLE casual sportswear that’s going on. Look at it! Amazing! If this doesn’t prove that every man needs a tracksuit in his wardrobe, nothing will.

    Garment to buy: Adidas Originals Superstar Track Jacket (£55,

    Album track you’ll recognise: Boyz-n-the-Hood by Eazy-E

  • 10 Style lessons from iconic album sleeves 9

    Pink Floyd – Wish You Were Here (1975)

    Who: English prog rockers, described by the Rock & Roll Hall Of Fame as “what George Orwell and Ray Bradbury were to literature, Pink Floyd is to popular music” in that they brought an entirely new dimension to the airwaves.

    The lesson: Never, ever scrimp on your tailoring. You simply cannot get away with a poorly-made, cheap suit (plus you’ll probably end up with third degree burns if you stand too close to a naked flame while wearing it). A suit should be a modern man’s luxury splash-out item, but that’s not to say you need to spend a small fortune. You’ll get some superbly made off-the-rail two-pieces if you do your research first. 

    Garment to buy: Hackett Lightweight Wool Suit (£545,

    Album track you’ll recognise: Shine On You Crazy Diamond


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Chris Sayer

Chris Sayer is a freelance journalist and editor based in London. Chris has interviewed some of the biggest names in entertainment and travelled the world doing an all manner of adventures for lots of brilliant magazines. He writes for Shortlist about booze but would probably prefer we let him write about fishing instead. Follow Chris on Twitter: @ChrisSayer00

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