Looking for a winter hat

I am follically challenged and have a huge melon as well. I enjoy wearing hats in all seasons, so I will give you a couple of my staples for winter. I wear a Lite Felt Fedora for the more formal days (try Shushans in New Orleans as they have a huge selection) and I really like the Kangol 504 wool (newsboy style) worn bill forward. If you want to transfer either of those styles to the warmer months, fedoras and newsboys come in different lightweight materials such as straw, cloth, and even paper (surprisingly durable).

My wife likes Stormy Kromer hats with the ear flaps that you can lower. Not my style, but she has converted our kids and several of our friends, both male and female. The Canadian Ski Team donned Kromers at the last winter Olympics. One last bit of advise is that black wool shows every piece of lint and stray hair. I don't know why, but it does. I would choose a strong gray, Loden green, or Brown before choosing black. Just my 2 cents.

Interesting summer traction on this thread.

My favourite winter hat is a Tilley Ivy Cap. Fold away ear warmers. By far the warmest hat I've worn. Would work well in a business sort of environment. I love it!

I work on top of Beacon Hill in Boston and it gets freezing cold and snowy and every type of weather. I also wear a suit to work, so a knit cap or bomber/aviator looks a little out of place. I have two hats, one is a tweed flat cap. The flat cap can be helpful if I need to head out somewhere during the day because it folds up and I can keep it in my overcoat pocket.

The other is a wool fedora. The fedora is great because it allows some air circulation (commuting up the hill can be tiring) but holds the heat and the brim actually keeps the warm air from my head/face from just dissipating and keeps my ears warm (enough). I have a fairly round face so I needed to try on several models in both of these styles. My number one recommendation is to try them on (and I apologize if this is a no-brainer); I had looked at several models that I thought would look good when I saw them online, but when I actually went into a store, they didn't at all. And the fedora I ended up buying was one that I didn't think would look good at all but ended up looking great.

I would go for a winter Tilley hat if you want something that will keep you warm and look conservative. They also have hidden ear flaps for the really cold windy days.
http://www.tilley.com/canada_en/shop_men?cat=44&t_filter_category=641
Outside of that I would suggest a nice fedora. Brim for sun protection. Keeps your head nice and toasty. You can get ear warmers that wrap around the back of your head for those really cold days. It ends up being a three season hat. Maybe a year round hat depending on how hot summer gets.
My two cents worth.
Johnny

I wear this particular Tilley in the occasionally cold, damp weather of North Texas. Good protection from the elements, fold-down ear flaps and warm.

To resurrect this thread, I finally bought a hat today. I selected a Goorin Ski Cabin Flat Cap in black. It's made out of wool-poly and has fold-in ear flaps. I think this is going to work well for me!

Thank you, again, gentlemen, for the feedback!

Random Shaver said:

To resurrect this thread, I finally bought a hat today. I selected a Goorin Ski Cabin Flat Cap in black. It's made out of wool-poly and has fold-in ear flaps. I think this is going to work well for me!

Thank you, again, gentlemen, for the feedback!

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That's sharp.

Every gentleman over a certain age should have a Harris Tweed flat cap for the winter - flat top like this, not the newsboy stye with a button on top.

And as an addition, perhaps a moleskin one like this.

Random Shaver said:

To resurrect this thread, I finally bought a hat today. I selected a Goorin Ski Cabin Flat Cap in black. It's made out of wool-poly and has fold-in ear flaps. I think this is going to work well for me!

Thank you, again, gentlemen, for the feedback!

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Ah, I hadn't realised this was an old thread!

That's a nice-looking cap

Oscroft said:

Ah, I hadn't realised this was an old thread!
That's a nice-looking cap

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No worries, sir! Thank you for the feedback and your kind words.

August West said:

That's sharp.

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Thanks! I'm excited to have it. This is one of those "finishing touch" things that I've been meaning to get around to but haven't. Now that the weather is rapidly cooling, I had every impetus to do so... and thus it was done!