The Shirt Every Gentleman Must Own

Every well dressed gentlemen must have an all-cotton oxford cloth button-down shirt originally offered by Brooks Brothers, but J. Press now offers the best version.

Every well dressed gentlemen must have an all-cotton oxford cloth button-down shirt originally offered by Brooks Brothers, but J. Press now offers the best version.

Kamakura, a Japanese purveyor also has a superior version, but their customer service is not dependable.

The shirt’s button-down collar was originally called a “polo-collar,” as the button-down feature was designed so the collar would remain in place instead of flapping up in your face during a vigorous game of polo. This classic — an import from England — was first sighted in 1897 on the polo fields of Long Island.

F. Scott Fitzgerald, Bobby Kennedy, George H.W. Bush, and Andy Warhol sported this style on occasion. Fiat industrialist and notorious Playboy Gianni Agnelli famously wore his wristwatch on the outside of the cuff of his.

The “roll” of the collar is crucial. Lower-budget makers never get the collar roll or the length of the collar points right. J. Press has mastered this.

Eschew the permanent press "non-iron" model. The longer you own this all-cotton shirt and the more times you wash it, the softer and more comfortable it will become. Considered a more informal dress shirt; it is acceptable with a blazer, a sports jacket or a single-breasted suit, usually paired with a regimental striped tie, knit tie or saucy bow-tie.

Never wear a button-down collared shirt with a double-breasted suit. The more formal double-breasted suit looks best with the more formal spread or long-point collar. Fred Astaire broke this rule, but you’re not Fred Astaire.

A Oxford cloth button-down with an unfastened collar, rolled-up sleeves and jeans makes for a comfortable, casual look. The shirt traditionally comes in white, light blue, pink, blue and white stripes and pink and white stripes. It also comes in yellow, but yellow is a tricky color for most men, depending on their complexion and coloring. Yellow looks good with a brown suit, but then a brown suit never looks good.