eggert fur hat

A reader recently asked me what hat I wear during the winter. It breaks down into three options:

The trilby

A ‘proper hat’, as many people seem to refer to it, a trilby or fedora is the default option with tailoring. I have worn Christy’s, Bates, Lock and Borsalino, but my favourite is the Traveller model from Lock’s.

The Traveller is made of a thin felt and is unlined. This is intended to make it easy to roll up and travel with, which you can certainly do, but the biggest advantage for me is that it makes the hat softer and more casual. The brim is never perfect, never crisp and sharp, and I find that makes it easier to wear with tweed jacket, even leather. Try turning the brim down all the way round for a more casual look too.    


The beanie

Sadly, the default choice for men these days. Scared of a ‘proper hat’ and with few other options, men go uncovered or wear a too-casual beanie with too-formal tailoring.

A beanie can sometimes work, however, particularly with tweed or a big overcoat. It just needs to be the most formal version of a beanie there is: dark, thin and short. Most beanies are too thick, making them warmer but casual. A smarter one would be made of thin cashmere, with light ribbing. Most are also worn too low on the head – roll it up higher, so not all the ear is covered. And navy is obviously the smartest colour, though mid-grey (again, obviously) is a good second.

Elia Caliendo works this look particularly well. I have two of his hats from Milan – I will dig out the details for a future post and take a few photos.

The fur hat

As shown in the top photo. These are from Eggert, the Icelandic furrier stocked at Anderson & Sheppard – a wonderful man, who I was fortunate enough to meet recently and will write more about soon.

This is hat as accessory rather than necessity, but it is very warm and mine has kept my head cosy in Moscow, Scotland and Milan (the coldest of the three). Worn either formally or casually, it is a great option. Mine is deerskin with racoon fur I believe, and cost £450.

Top image: Luke Carby, at Anderson & Sheppard. Middle image: High Snobiety, from Pitti Uomo January 2013

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“Most beanies are too thick, making them warmer but casual…Most are also worn too low on the head – roll it up higher, so not all the ear is covered.”

I think you have sadly missed the point of wearing a hat.


Thanks for this, Simon! I recently started wearing a “proper hat” this winter, and have been loving it. I have noticed that it’s a bit of a social experiment though, to see if anyone says anything about it…but that’s a different story. 🙂

That said, I’d like to add one company to the pile – I ordered my trilby from the fabulous Optimo Fine Hats in Chicago ( I cannot recommend them more highly. The construction is magnificent, and the hat has already taken a beating from both heavy weather and international travel and doesn’t event look a little worse for the wear. Moreover, their customer service was nothing short of awesome – the hat was made-to-order relatively quickly and the staff was incredibly tolerant of my hat-ignorance, answering tons of stupid questions along the way. Not sure if you’re aware of these guys, but wanted to put them on the radar. Happy New Year!

Damian Corley


Thank you so much for referral to Optimo Fine Hats in Chicago. One word to describe their hats, amazing!


Brian Small

A trilby or a short beanie for winter: not wear I live! The fur hat is good though. The idea of “winter” has to be qualified. And I’ve done just that:

Matt Spaiser

The weather is especially cold today in New York! I wore one of my Lock trilbies, and in dark grey felt it looks great with my navy greatcoat. Whilst I love the hat I feel a little self-conscious wearing it. I don’t see anyone under 50 wearing them (I’m 26). I see younger men wearing cheap tweed trilbies, so I’ve been thinking about getting a nice one. What do you think about wearing those in the city? I work in a rather residential area of Manhattan, so I’m not amongst bankers. I also wear jackets and trousers, not suits, to work.


Forget the beanie and get yourself a decent flat cap in a proper harris tweed. Or a baker boy or deerstalker if you’re feeling more jaunty.

As for a formal hat to wear in the coldest weather, there is only one real option – the astrakhan. New, the genuine article is almost impossible to get hold of but they offer an unbeatable combination of elegance and warmth. I have a vintage Persian example that finishes above the ears, but is so warm you hardly notice.

Dan Ashlin

I have hats from Bates, Locke and several others. However, the best hats made in my opinion come from “Optimo Hats” in Chicago.



Do you ever wear the fur hat in London? Bold.


Dear Simon,

Winter is coming and I thought about getting my first real Hat (I just saw that Drakes has new rollable trilbies). Now I wondered: would you advise me to buy a brown one first, or would dark olive be a suitable and versatile colour? Normally I would opt for brown, but I have a brown coat which I wear quite often.

Thank you very much in advance


Simon, do you think that recent calls (in the news again this day) for the banning of fur could effect fur felt hats? If so might it be a good time now to stock up on fedoras?


I don’t like winter hats as they mess up my hair.

Do you know where I could find quality men’s ear warmers? Preferably those that wrap round the back of the head so as to not disturb the hair.

I have been searching for quality ear warmers for men for years now with no luck and am asking myself if I’m the only one having this problem? Would you ever think about wearing something like that or am I the only one?