“Timelessness”: Classic Cool or Basic Boring?

March 3rd, 2014

This weekend I fell into an interesting conversation about the boom of traditional menswear and the resurgence of classicism among young men. It’s no secret that our fashion-conscious generation appreciates tailored suits, wears classic felt hats, and understands the long-lasting value of old world things like goodyear welted shoes.

That said, there exists an interesting dichotomy in modern men’s style. On one hand, guys want to use personal style to express their individuality and show the world their true colors. On the other hand, guys want to conform and look “timeless”; in such a literal way that if a black & white photograph were taken, it should be impossible to determine its date.

The desire to look timeless, in my opinion, comes from the glamorization of 1950s-era Hollywood icons (guys like James Dean and Steve McQueen), the practicality and economic benefit of investing in pieces that can be worn over a long period of time, and the fear of looking back at old photos and saying: “Damn, what was I thinking?”. This combination causes many men to favor a nondescript uniform of menswear staples that date back to the 1950s; things like oxford cloth shirts, khaki chinos and crewneck sweaters.

But where is the fun in that?!

Personally, I love looking back at old photos and being reminded of a specific time, place, and frame of mind. My style is constantly changing, just as I am, so when I see an old photo (even in the archives of Articles of Style) I usually think “Damn, that was such a different time in my life. I thought differently, acted differently, and of course, dressed differently”.

There was my Allen Iverson period, for example. In ninth grade I wore exclusively baggy streetwear brands like Rocawear, FUBU, and Sean John and even had my hair braided in cornrows… I was nice on the court though, don’t get it twisted. After the cornrows I let my hair out and permed it with tight curlers, going for more of a smooth Michael Jackson/Lionel Richie vibe (and only listening to old school R&B like R.Kelly and the Isley Brothers). Point being, I would never trade those distinct memories and experiences for an everyday oxford cloth button-down and khakis.

On a similar note, as much as I appreciate the classic styling of all-American guys like Paul Newman and Cary Grant, I get much more excited about the polarizing non-conformist styles of icons like Michael Jackson in the 80s, or risk takers like Lapo Elkann. These are men who have used their unique sense of dress to amplify their characters, and in turn, their careers.

As I’ve written before, investing in a classic wardrobe can have you “well-dressed” for any occasion, but personal style can tell you a lot about a person…


So what side of this men’s style dichotomy or you on?


Looking forward to your comments below.


Yours in style,

Dan Trepanier