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Context, outfit and age appropriateness are the keys. Film stars, pop stars and footballers can do so much more outre than we mere plebians. They have minders, for instance, and so may well be able to brave the streets sporting the latest ridiculous nut-knitwear (avec or sans bobble) without fear of physical attack. I suspect our bonce-covering has to be more circumspect.
Any headgear worn in town by a gentleman over the age of 25 should be considered an affectation . Brave the elements and try to appear less ‘soft ‘ .
Striped Beanies, Flat caps and Fedoras in Tweed or Felt are VERY becoming.
I am sure the kids of Liverpool will be impressed.
I’d avoid the current fad for skater-style woollens rolled up on the crown in a nautical manner however -this style won’t last.
Can’t do it at all without looking a bit, well, either self posessed, or just a bit daft. The challenge is damage limitation.
If it is wollen, it should sit tight to the head, unless the head is unusually pointy or potato shaped.
If it has a brim, it has to look like it will both keep the water off, and fly well when launched across a crowded pub.
Wearing a cap for a gentleman is a matter of practicality. If its cold, wet, hot, or sunny and bright there are hats for all occassions. The important thing is to where a hat with confidence. Where the hat because it makes you more comfortable and less exposed to the elements. Where the hat because you are smarter than the other guy who is now wet cold and miserable, or blinded by the sun, or worse has a sunburn on his head and face. Be bold and be beautiful, where a hat, any hat, and be proud.
Brown plaid with ear flaps lined in cashmere. Sort of a baseball cap crossed with a flat cap cum furry bear hat thingies. Genius. Bought said piece of head wear in an old man shop somewhere in darkest, provincial Italy. A thing of real beauty. Urban Country Gent. Why on earth did I decide to leave in on the train? Oh, how I miss thee. Winters have never been the same since…
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