My Kinda Clothes: Dressing Like It’s 1959 At A Canadian High School

As a high school student, interchangeable items are a must. This means a few simple items that can work with everything else I have in my wardrobe. I would say that I have a uniform, which consists of an OCBD in white or blue, a knit or repp tie, khakis or indigo denim, a sweater and a Barbour.

I rely heavily on thrift stores for my ties and jackets. My most treasured items are my late ’50s tweed jacket and my Chipp silk knit. Because of the cold, damp weather of Vancouver, I am unable to wear loafers for much of the year, so I opt for chukka boots. As a 16-year-old who tries to dress like it’s 1959, I can attract a certain level of attention among my peers. I have not had any negative comments on my choice of attire for almost two years; I believe people have grown to accept that not everyone wears ripped jeans and oversized hoodies.

My personal style, Neo-Ivy, has been influenced by brands like Drakes and J.Crew. Purists may scoff at my inclusion of denim and boots, but it is purely a functional choice. Given the chance, I would don penny loafers and desert boots, but the weather isn’t exactly cooperative. Although I have a modern interpretation of trad, I wouldn’t hesitate for a second to make a pilgrimage to the Andover Shop or J. Press. Maybe someday. — ROBERT STAEHLING

27 Comments on "My Kinda Clothes: Dressing Like It’s 1959 At A Canadian High School"

  1. Caustic Man | January 9, 2019 at 6:56 pm |

    You look good. And keep experimenting. Nothing in life is static, not least Ivy style. So wear your boots and denim joyfully.

  2. Miles Coverdale | January 9, 2019 at 7:58 pm |

    I wish I had your taste when I was your age. For footwear, I think L.L. Bean duck boots–low moc style–would work well with much of your weather.

  3. Robert, you missed a crucial point: you didn’t tell us how you came to desire to dress like it’s 1959!

  4. Richard E. Press | January 9, 2019 at 8:50 pm |

    Robert, keep rocking.

  5. CanadianTrad | January 9, 2019 at 9:24 pm |

    Great to see another Canadian Trad. When I was 16 back in the 90s, I mostly wore a Canadian tuxedo and Beatles t-shirts. Hell, I don’t dress as well as you most days now.

  6. Bravo Robert!!!

  7. Evan Everhart | January 10, 2019 at 12:04 am |

    Excellent taste amd sgyle Robert! I wish I could see more similarly attired young (or old) people in Los Angeles! Bean boots are pretty prime for yr typical weather up North there, as previously stated by Miles Coverdale. They’re pretty indispensable, and look great with a Barbour, or a Mackinaw. Wave that Trad flag high!

  8. Old School Tie | January 10, 2019 at 12:34 am |

    Interesting that a young lad is expressing his individuality at school by wearing clothes whose origin stems from conformity, particularly that found in educational establishments.

  9. As pointed out by Christian, I did miss a point; I got into the style through film. Movies like Bullit, The Graduate and the Bond films of the 60s were big influences. Style bloggers like Ethan M Wong and OxfordClothButtonDown have also greatly inspired me.

  10. I went to a Vancouver high school with a mandatory uniform, and the students (self-consciously dressing down in a passive, Canadian act of rebellion) didn’t have half the panache that you do, Robert. Well done!

  11. Hell yeah! Wonderful to see a young man dressing far better than the average in 2019. You look great.

    Best Regards,

  12. Robert, keep in mind that the negative comments you receive are from jealous peers who envy the attention you get from teachers and girls.

    And keep up the good work!

  13. Charlottesville | January 10, 2019 at 10:28 am |

    Robert – What a great look. As others have said, I wish I had your taste and sense of style in my teens. Just terrific.

  14. Good choices + good fit. Plenty of denim in Take Ivy. Boots – why not? My only recommendation would be a different belt – I like Sid Mashburn belt buckles – i.e.

  15. Trevor Jones | January 10, 2019 at 11:12 am |

    Nice work, Robert. Great article and nice outfits you have there.
    Christian, I really like this ongoing column, hope to see more regular additons. It’s so cool to see what others are wearing and their individual takes on classic items.
    Old School Tie, I agree – pretty ironic that a mode of dress once used as a sign of conformity and establishment morals is now a radical symbol of individualism.

  16. The most authentically 1959-ish element are those white socks.

    I know lots of people who habitually dress in an affectedly retro manner (mostly due to rockabilly scene associations) and none, but none, of them ever go so far as to wear the period-correct white socks.

  17. Well done, Robert. One bit of avuncular advice: find a thin belt somewhere, thrift store or big discount chain. It’ll make a big difference with the look you’re going for.

  18. Christian
    I actually got a thin belt in oxblood a few days ago! Wish I had gotten it earlier to put in the post

  19. Carmelo Pugliatti | January 10, 2019 at 3:16 pm |

    1959 is a perfect year.
    Maybe the heaven is a eternal 1959 ( if not,is a eternal 1955).

  20. Stacy G. Kelly | January 10, 2019 at 4:27 pm |

    Dear Robert,
    From a fellow, albeit much older, Canuck- bravo indeed! Reminds me of Anthony Michael Hall circa “The Breakfast Club”. Agreed with the Bean Boots suggestion. Would be great Trad addition for Vancouver’s climate (Or, as Ferris Bueller would say, “It is so choice”). Love that you are pursuing your own sartorial expression. Keep it up!

  21. Ha. I was about to say I dig the belt. Well, I really dig the pinned collar.

  22. Robert, a thin belt as in 1-1/4” not 1-1/2”

  23. Robert,
    If you don’t already have one, look into getting a navy grenadine necktie. I think you’ll like it.

  24. Keep it up and thanks for the mention! DM me on Instagram when you get a chance.

  25. Hardbopper | July 17, 2019 at 4:49 pm |

    The crew neck sweater with the light blue edge on the collar. Please, Robert or anyone else, tell me more about this.

  26. David Mulcahy | November 30, 2019 at 8:28 pm |

    Great to see someone at 16 with style, not fashion. I’m 19 and dress similar here in Ireland, unfortunately I stand out heavily because very few dress traditionally at all here. Keep it up, your ensemble is great.

  27. Good job, Robert! I’m older than you but live in a similar climate. I actually think your shoes are perfect for the outfit, I do a similar look in wet weather, and penny loafers when it’s nice.

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