Classic Menswear 101

Classic Menswear

The classics are wardrobe items that have been around, stood the test of time, and keep on going.  Jeans, khakis, blue oxford button down collar shirts, rep stripe ties, navy blazers.  These are all classics now and they will be into the future… well, until we start wearing Star Trek type outfits that is.

The classics float from season to season, and outlast all the trends.  The classics laugh in the face of silly trends.  And here’s the secret to the classics:  you can create countless outfits from the right combination of pieces in your closet.

Photo and styling by your coach.

Classic Combinations to Get You Thinking

Reach for these, put them on, and walk out with the confidence that you look sharp, professional, and comfortable.

Let’s start with a few of the simplest combinations first - pants, shirt, and the right kind of shoes:

  • #1 Flat front khakis and an oxford blue, button down collar shirt, with a brown belt and brown shoes such as:
  • #2 Dark jeans with a white dress shirt, black belt and black shoes like these Eccos that I own:
  • #3 Black flat front pants with a blue and white checked shirt, black belt and classic white sneakers like these:

Get the shoes right, dude.  There are way too many companies out there making ugly ass shoes and guys keep buying them.  I'll even say that if you do nothing else that I recommend, improve your shoe game.

Alright that's it for today's style coaching session.

Get on it,

Coach Jeff


Menswear designer, artist, author, digital usability strategist, coach. I'm one of those guys who've done a lot in life and now I want to share it. I've traveled and worked across the globe and still have a lot left to accomplish.