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The dos and don'ts of winter hat wearing

Hats on parade at the Pitti Uomo men's fashion trade fair
Hats on parade at the Pitti Uomo men's fashion trade fair

Allow me to paint you two opposing vignettes. One is of an Italian man of a certain age cutting a dash through frosty Milan earlier this week, classically patrician in his style, a handsome suit and wearing a coat draped over his shoulders like only an Italian man of a certain age can, topped off with a pristine fedora.

Felt trilby, £195, Anderson & Sheppard
Felt trilby, £195, Anderson & Sheppard

The effect was pin sharp and utterly polished; a masterclass in continental refinement. The second scene that springs to mind when I ever attempt a foray into the world of hat adorning is of me, seduced by the winsome thought that I would look good in a Greek fisherman’s hat (a sort of more structured flat cap) looking into the mirror to find Blakey from On The Buses staring back at him. 

Felt Piuma hat, £330, Borsalino
Felt Piuma hat, £330, Borsalino

Hats are a tricky beast to negotiate; some seem to have a natural knack for wearing them, others - myself including - not so much. The bi-annual trade fair Pitti Uomo in Florence is a showcase of some of the world’s most flamboyant sartorial peacocks, with hats a key component of their meticulously studied “looks”, yet for every David Beckham in a sharp fedora or cosy beanie hat, there’s…well, David Beckham in a questionable flat cap looking like an extra from Peaky Blinders. The difficulty with hats is that they can veer into costume territory, and all too often make the wearer a tad self conscious. 

Stafford fedora, £295, Lock & Co. Hatters
Stafford fedora, £295, Lock & Co. Hatters

Which is a pity, because certain hats can be an object of beauty in their own right; take in the sculptural form of a Borsalino, for example, or the weighty elegance of a Lock & Co. Hatters bowler hat in inky felt. The craftsmanship that goes into making such models is astounding in itself; that particular British institution boasts the title of ‘oldest hat shop in the world’ and still operates from its original  St James’s site, which make the process of trying one on a veritable experiential history lesson. 

Wool beanie, £70, Ami Paris
Wool beanie, £70, Ami Paris

So which hat style to plump for as temperatures drop? A hat enthusiast friend (he commissioned the costume designer behind Tom Hardy’s period drama Taboo to make him one of the ‘informal’ top hats) advises that a hat should balance the shape of the face - long and thin faces need a wider, shorter shape, rounder faces need something with more structure (perhaps this is why I fell at the first hurdle with my collapsing mushroom of a hat).

Cashmere beanie, £110, Officine Generale
Cashmere beanie, £110, Officine Generale

Stylistically, despite efforts by Gucci to add a high fashion gloss to the trapper hat, anything that’s too rustically “outdoorsy” can look a tad ‘gap year ski instructor’’; opt for a beanie by all means but forgo the long, floppy shapes for one that’s shorter and more neat, and unless you are attending a festival or under the age of 12, avoid bobbles and buckets. Our Milanese gent would never stand for such sloppy affairs.