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Wardrobe Staple: The Denim Trucker Jacket

September 13th, 2012

It’s Fall again! A style lover’s favorite season. Soon we can stop dreaming about layers of cashmeres, flannels and tweeds.

Don’t be too eager and break out the heavy outerwear right away, though. Start transitioning your wardrobe slowly as the temperature drops using light jackets and thin layering pieces.

Now’s the perfect time for an early Fall staple: the denim jacket.

Here are three of my favorites.

1. Ditch the Blazer

Ditch the suit jacket or sports coat for a cooler, sportier alternative.

A crisp trucker in dark indigo is perfect for commuting to the office on a casual Friday.

This time of year, warm during the day and cool at night, calls for a foundation of lightweight pieces (poplin shirt and hopsack trousers) combined with slightly more Fall appropriate pieces like the denim jacket and wool tie.

A good menswear outfit is rooted in classic, versatile pieces – making it easy to swap out items to change the look.

For example, swap the shirt/tie for a white tee and the lace-ups for low-top sneakers…now it’s a whole new casual look.

  • Black/Grey shades by Matsuda Eyewear ·
  • Indigo denim jacket by Levis ·
  • Blue stripe shirt by Ralph Lauren Polo ·
  • Navy/Grey/Black Wool Striped Tie by JCrew ·
  • Silver 2″ tie bar by Tiffany & Co ·
  • Black alligator belt and silver buckle by Ralph Lauren Purple Label ·
  • Black leather/suede spectator wingtip shoes by Barker Black ·
  • Watch by Montblanc Timewalker Automatic ·
  • Black alligator watch band by Montblanc

2. All Black Everything

For me, some days just call for all black…usually if I’m grinding on a project, or planning to be out late.

It’s funny to say, but it’s true, wearing all black can ad a hint of rebellion, which can be translated into confidence. I remember our basketball team used to wear all black sneakers on the court because it was “intimidating”…same idea I guess.


For a tonal look, ad depth and texture by mixing various fabrics and finishes. For example: the jacket is waxed, the jeans are matte, the henley is a silk blend with sheen, the loafers are polished leather, the belt and watch strap are alligator, etc.

If you don’t have a pair of go-to penny loafers, get some.

You will find yourself wearing them with everything.

  • Gold Plated hand-engraved shades by Matsuda ·
  • Black Waxed Denim Jacket by Helmut Lang ·
  • Black cotton henley by Burberry London ·
  • Black denim jeans by Rag & Bone ·
  • Black leather penny loafers by Bass Weejun ·
  • Watch by Montblanc Timewalker Automatic ·
  • Black alligator watch band by Montblanc ·
  • Necklaces from NYC Street Artist

3. Tailored Casual

A beat-up vintage jacket can contrast the stuffiness of a cleaner preppy look. It ads a little character and charm,

The fit of the jacket is very important, especially if it’s vintage. It should be slim through the body and sleeves, hugging the body and hitting just past the waistband.

In my opinion, the seasonal color palette of a man’s wardrobe should subtly reflect that of nature.

Come Fall, start thinking about deeper tones like earthy greens, rich browns, deep blues…

These are the same loafers as the pair in look 2, just brown.

For the price, durability and versatility, Weejuns are among the best values in footwear.

  • Gold Plated hand-engraved shades by Matsuda ·
  • Denim jacket by Levis Vintage ·
  • Camel hopsack Vest ·
  • Brown check plaid shirt ·
  • Navy knit tie by Polo Ralph Lauren ·
  • Silver collar pin by WANT ·
  • Forest green cotton suit trousers ·
  • Brown Penny Loafers by Bass Weejun x Barneys ·
  • Watch by Montblanc Timewalker Automatic ·
  • Nato Striped grosgrain watch strap by Corvus

Thanks for reading.

Yours in style,

Dan Trepanier

Photography by Alex Crawford.