Hats for The Modern Gentlemen

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Strange” wrote Graham Greene, in relation to his character Henry Miles, “how much dignity there can be in a hat. Without it he looked like one of the anonymous, the dispossessed.” From a 1951 perspective Mr Greene’s observation is accurate; hats were everyday accessories of gentlemen and barrow boys alike. Men of purpose and place had headgear.

However, in the late 1960s and early 70s, perceptions of acceptable fashion changed considerably, and hats became embarrassing, almost comical reminders of what once was. By the 1980s, hats had all but vanished from the radar of everyday fashion for men; baseball caps were sported by tennis shoe CEO’s, and bowler hats by quaint old City stockbrokers, but the covering of the head on the street was a minority activity.

I doubt hats will ever regain the importance that they held for our ancestors in terms of fashion or comfort. The daily hat, once as much a part of our outward appearance as shoes or a pair of underpants, has died a death.

Being a dramatic at heart, I adore hats. I wish I could wear them better, and more often. I last wore a proper woven-fedora this summer, when the hot sunshine and high-spirits excused eccentricity. However, I have taken up hat-wearing quite seriously this autumn; a particularly cold end to September has forced me to cover my head. Here are some tips if you are experiencing blustery weather and feel ever the daredevil to show the world some chapeau chic.

Fedoras and trilbies


The hat of choice for the film noir gumshoe, the pinstriped gangsters of yore, and more recently, on occasion, Kate Moss, fedoras and trilbies are rarely seen these days. Race meetings such as the Grand National at Aintree are events at which this hat can enjoy ubiquity, elsewhere one will find that they are a mark of self-conscious individualism. Wearing them with putty mackintosh raincoats will look a little too Forties Hollywood, however, they can add effortless dash to an otherwise ordinary outfit. I have seen gentlemen wearing double breasted suits with dark fedoras. This combination is a little theatrical, but is very endearing and certainly does add that sprinkle of dignity.

Gatsby or newsboy cap

“Read all about it!” is the dull cliché phrase I have been assaulted with when wearing my own version of this hat. However, when worn with the right outfit; a corduroy two-button jacket, grey flannel trousers and chestnut brogues, for example, few will look as complete or wholesome. Much maligned for its association with baker boys and newsboys, I think many forget that it has also been worn by professional golfers   and the fictional character Jay Gatbsy. Such associations romanticise the headgear for me, and I enjoy the jaunty and youthful nature of it. Different to the fedora or trilby, it softens a look wonderfully well.

The other hat…

The beanie, although a structureless, poor excuse for a ‘hat’ is worthy of a mention as being a major part of modern headgear. The very practical and casual hat, which originated as warm protection for labourers in cold weather, is now frequently worn for winter sporting activities and in very cold weather in both bucolic and metropolitan situations. Although hardly elegant, it is a very useful and sometimes charming item of headgear which looks good when worn with looser and more casual outfits. Burberry Prorsum designer Christopher Bailey once teamed the oversized beanie with elegant single and double breasted suits for an eclectic yet very appealing look. Go for plain, darker colours and always wear oversized beanies down to the eyebrow.


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Winston Chesterfield is an amateur composer, fashion blogger, trained lawyer and style aficionado. He lives in Westminster, London and blogs at www.levraiwinston.com.

Comments

  1. Roderick Mallia says:

    Great article. Just two little questions: (1) Should a fedora/trilby always be worn with a suit (ergo, a formal attire)? (2) Should the colour of a hat always match a suit? Would complementary colours (dark grey hat, black suit, for example) look bad?

  2. editor says:

    (1) For me a fedora means dressing up. Debate on where is the line between formal and casual is open for discussion but you surely won’t be wearing fedoras with hoodies.
    (2) Colors don’t need to match but they should be complementary or better yet look good together, as is the case with any clothing pieces combined.

  3. Roderick Mallia says:

    Cheers! Thanks Ed!

  4. Mike Poplawski says:

    I onw a copule of fedoras and trilbeys. I have been curous about the colors too. What I have seen, from the 30′s and 40′s is a lot of browns. It is almost as if men had only one hat so they went with color that was subdued and didn’t clash. I own a brown and also a gray (very Gregory Peck). The brown does seem to go with most everything. I also have a Panama which seems to go with everything and is very very sharp looking – but that is a summer thing.

  5. Mike Poplawski says:

    Pardon my previous email’s mispellings..I hit the “send” button before proof reading.