David Sedaris once lamented that a gentleman has too few options for accessorizing his outfits.

In an effort to to add flair to his wardrobe, he resorted to what I consider to be rather extreme measures. Accessorizing a masculine outfit requires a certain creativity, I must admit.  One might find cuff links too innocuous, ascots too Britannic, fobs too likely to catch on a door handle and pocket squares too difficult to match to one’s shirt — not to mention the countless folding styles one must master.  But a gentleman can comfortably say a great deal with the selection of his hat. Here, options abound. What’s more, the proper choice in headwear can help define a personality. In some cases, a hat can be iconic.

This slideshow requires JavaScript.

Certainly we are familiar with the the most famous of such examples: the bowler that seemed always to tumble from the head of Charlie Chaplain, the Fedora that seemed somehow stapled to the head of Indiana Jones, the pith helmet that Winston Churchill wore as he roistered across the North African Desert in pursuit of Rommel or the deerstalker for which Sherlock Holmes is so well known but never mentioned to have worn in any of the books about him. But these were not the hats of men of sport — a sporting gentleman wears other such hats.

In an effort to maintain the theme of my previous post, I will continue with hats that might complement a tweedy gentleman, describing each of these hats fully:

Sean Connery complements his jacket with a Newsboy Cap.

The Newsboy Cap, or Gatsby Cap, is a style that flatters nearly any outfit—from blue jeans to plus-four knickers. Its versatility makes this hat the best first pick to include in one’s wardrobe.

Sean Connery again pairs his jacket to a hat, this time playing Henry Jones in 'Indiana Jones and the Last Crusade.'

It is a shame, I think, that the Eske Cap is associated more with the emeritus station of gentlemanly sportsman. However, one mustn’t dodder to don this dapper topper.

The man plays himself, in an English Driving Cap.

The English Driving Cap, or Flat Cap, is designed specifically to keep itself atop one’s head while touring in a topless sports car. During a speedy country drive in your Triumph Spitfire, be sure to angle down the brim, lest Bournolli’s Principle extract your hat from your head.

Sean Connery in years long past wearing a Skipper Cap.

The Skipper Cap was once a favorite among the fisherman of Donegal Bay, but later became known as the preferred headwear of the Molly Maguires who took to blowing up Pennsylvania coal mines for the sake of Irish immigrant rights. In this hat, a modern gentleman cannot help but look a skosh rogue and dangerous.

Clearly, while conducting my sartorial research these past two weeks, I could not escape the ubiquity of the greatest living Scot. However, I shall now, finally, put the issues of tweed and Sean Connery to rest.

Next week, I will consider very seriously the importance of polishing and preserving one’s fine footwear.

*  *  *  *  *

For further reading on the life and times of a gentleman humorist, I recommend::

Sedaris, David, When You Are Engulfed in Flames, Little

For further reading on the adventures and exploits of the Molly Maguires, I recommend:

Burke, William H, Anthracite Lads: A True Story of the Fabled Molly Maguires


Trackbacks / Pingbacks

  1. Hats « Modern Gentleman - September 23, 2011
  2. Outdoor Attire, Hats « KM Parentin - September 23, 2011

Please tell Nichol and Dudley what you think:

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s