I’m a man who believes fashion should be fun, but even I have to admit that keeping up with changing fads can be a pain.  From carpenter jeans to Ed Hardy t-shirts (shudder), trends have come and go through my life that have left me not only stripped of my dignity, but with a hole in my wallet as well.  Thankfully, a few years ago I became fed up and took a look in my dad’s closet for some money-saving inspiration, and what I found astounded me.  Instead of dated clothing, I discovered classic items – tweed jackets, knit ties, rich brown wingtips – that like a fine wine, have only gotten better with age.  If you’re tired of chasing trends like I was and are looking for a way out, here are three more iconic pieces that are sure to stay in your wardrobe for years to come.

A lid with a story

It was long my opinion that one is either a hat man, or not a hat man.  Then I discovered trilby hats for men, the one cap that looks fantastic on anyone.  With a shorter brim than the average fedora and a reasonable sized crown, the trilby fits your head just so for precisely the right dash of refinement.  Plus, its legacy is matchless.  Frank Sinatra was rarely photographed without his trademark trilby, and the original 007, Sean Connery, wore one in the first five Bond films before relinquishing his throne.

A coat for the road

Long before bikers became known as tattooed cartoon characters or law-breaking speed freaks, a more elegant picture of the motorcyclist reigned.  Garment maker Belstaff knows this, because they produced and continue to produce iconic jackets for the weekend rider.  A favourite of motorcycle enthusiast Brad Pitt, the Belstaff jacket comes in a classic belted variety or, for the more modern man, an updated model that trims things up while retaining the same vintage appeal.  Simply put, this is the coolest riding jacket around.

The original bling

Contrary to the teachings of hip hop MCs and overzealous Beverly Hills housewives, there are more graceful ways to put your tastes on display than with outlandish bling.  For the ultimate statement in sophisticated style, try snatching up a few large face watches.  These bold watches manage to be both modish and restrained, and better yet, they can accommodate just about any price range.  I like to spend my days dreaming about the massive IWC Big Pilot, but for a more budget-friendly option, check out the Nixon Esquire watch at right.

What are your favourite iconic pieces?

Did you know?

Sean Connery’s 007 may be regarded as a style icon today, but Bond creator Ian Fleming was originally unhappy with the casting choice, calling the actor “overgrown” and unrefined.

-Jeff O.

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