Gents Among Men

Look Good, Live Well

30 Day Primer: Day 23 – Purchase Some Classics

30 Day Primer: Day 23 – Purchase Some Classics

You can never go wrong with purchasing timeless garments, and while there a ton of classic garments we can chose from we decided to narrow them down to four. 

From Steve McQueen (The Great Escape) to the sales associate in J-Crew, the brand, label or name may differ but you know the boots. Popular in the 1940’s, the Chukka boot was initially crafted with a crepe sole, and was considered the ideal casual boot. Like all great things, brands such as Alden® for J. Crew reinvented the iconic boot in a slimmer silhouette and hard bottom sole. I admit, hard bottoms are easier to transition from casual to formal, but you have a still love a classic. Clarks is offer the “original” crepe bottom option that you can pair with jeans, chinos or cord trousers.


The Trucker Jacket first entered the scene around 1905. The original Levi’s 506xx was produced out of 9 oz. denim, but didn’t adopt “jacket” name until it appeared in the denim’s company catalog in the 1930’s. The tucker jacket took on three versions or “types” before evolving into what we have now: the 1962 Levi’s 557xx double pocket “type 3” jacket.

The trucker jacket has been worn by everyone from artist, activist, actors, cowboys, and rock stars. The trucker jacket defines American history and remains to this day one of the best piece of clothing anyone could own. 


If you are thinking of investing in a sports jacket, rethink your idea of black. A black sports-jacket is considered a staple piece in every man’s closet, but a navy blue jacket offers more character and versatility. Navy plays as a neutral for the conservative male and for the creative type. Navy blue can be coordinated with a vast amount of colors.


The navy chino has always been a safe option to turn towards when choosing a staple bottom. They range from light winter wools, to crisp-clean summer cotton fabrics, and remain fully versatile when deciding to pair them with various shirt and tie combinations, or your favorite polo on the weekend.

Chukka Sketch by Han Josef for Gents Among Men