Our guide to the top 3 best winter hats for men

It’s time for your bucket hats and caps to hibernate to the back of your closet, we’ve rounded up the best hats for men. Don’t say it, don’t say, ah whatever - Winter Is Coming. And like a modern-day Jon Snow it’s time to get wrapped up in your warmest clothes, just swap the fur for some stylish winter headwear and you’re good to go. We’ve rounded up the best winter hats to keep you warm in style.

What is the best winter hat?

So obviously a winter hat should be suitable for winter, meaning it keeps that handsome head of yours warm. But since you’re not the kind of guy to put on any old hat, you want one that suits your style. Are you more of a relaxed beanie guy or a dapper fedora hat man? You’ll figure it out, I’m sure. Besides having it suit your style you want the winter headwear to be versatile and suit both that denim jacket you wear when the temperature is still bearable, your winter coat and if you’re the kind of guy to have multiple winter coats you want it to suit them all. That means they should have a timeless appeal, no huge logos and if you’re wearing logos on your beanie choose more subtle logos at least. You’re a grown man, better start dressing like one.

The Beanie

Why you should go for a beanie:

A beanie works perfectly when you have a relaxed style or when you’re out and about in your off-duty look. It has a cool, casual appeal and it looks like you don’t need much effort to look this good. Beanies are also the hat of choice for streetwear fanatics, blending in well with your OFF-WHITE jumpers and Yeezy Adidas sneakers, replace the beanie with a fedora hat and you’d look like you’re lost in the world of fashion.  

How to style your beanie

Headwear connoisseurs might be judging me now for putting these in the same category, but honestly, you’re a hat connoisseur so not sure I should be worried too much… What I’m trying to say is if you’re totally vibing on that workwear style then roll up your beanie or buy a ready-made fisherman beanie. This goes well with your Carhartt jacket and red wing boots.

The thing about beanies is that they can look a little sloppy, so avoid wearing them with an old jumper and baggy jeans – or just save that look for lazy weekends. Instead, style your beanie with a turtle neck or a denim shirt and some tailored pants. In this outfit go for luxury options that are from cashmere or soft cotton or wool. To really mix things up pair your beanie with your wool winter suit and an overcoat, for an I’m the boss here but still really cool vibe. 

The Flat Cap

Why you should go for a Flat Cap:

The Flat Cap serves instant old school vibes, but it’s working-class heritage also gives it a little bit of a rebellious edge. It has the same level of dapper as the Fedora hat, but it’s not so much of a big step or grand style move to make. Also, the Beckham men are a big fan, so that should be enough reason in itself.

How to style a flat cap

You want to look like a modern dandy, not a full-on peaky blinders character. That means staying away from suspenders and waistcoats to avoid it looking too much like a costume unless you figure out a way of doing this subtly.

A flat cap looks best with a polished winter coat that has a bit of tailored feel to it and comes in a neutral shade. Get super cosy in a wool jumper or wear it with your wool suit and brogues, just make sure the suit has a modern sleek feel, if you need inspiration for this just look up David Gandy – he’s the modern god of flat caps if you ask me (not just because I enjoy looking up his gorgeous face). You can also easily keep wearing it in summer with jeans and a T-shirt.

The Fedora Hat

Why you should go for a Fedora:

I cannot think of a classier hat than the Fedora, put on one of these baby’s and I swear you will feel like a different man. The fedora has earned its place as one of the top 3 best winter hats, by being an easy way to trick people into thinking you’re sartorially well put together while being more versatile than you’d think.

How to style your Fedora hat:

First things first, by fedora hat I mean one of those big classy fedora hats not the ones with a smaller brim, you can leave those to Jason Mraz in his 2008 peak. Then you’ll need to pick one in a neutral shade, but unless you’re shopping in costume stores a colourful fedora will be hard to find anyway. Also good to note is not to wear your brown hat with a brown suit or a black hat with a black denim jacket, mix and match guys!

A fedora hat will add a little oomph to your suit,  throwing on a classic overcoat works best for a sophisticated mad men-esque look. You can also make a more casual look work by matching your fedora hat with a white T-shirt and dark unwashed jeans when it gets warmer, just have to warn you; this look is seriously swoon-worthy.