Wearing hats is hard.
Get it wrong, and wearing a hat can make you look like a wannabe cowboy or reject from the Chicago Town gangsta collective.
But get it right, and you can position yourself as the most stylish guy in the room.
So how do you separate men’s stylish hats from tragic costume pieces? Gents, you’re in luck. In today’s article, I’m breaking out the top 5 styles of hat every man should wear this fall.
- The Flat Cap
- Beanie
- Baseball Cap
- Bowler Hat
- Trapper Hat
#1 The Flat Cap
Peaky Blinders fans will know this one – though I’d leave the deadly razor blades at home if I were you!
The flat cap is a classic headwear option that’s been worn by gents for centuries. Traditionally made from wool, the flat cap can now be found in a variety of materials, including cotton, tweed, and even leather.
But what makes this contender in my list of men’s stylish hats? It’s the versatility. The flat cap can be worn with everything from a pair of jeans and a t-shirt to a three-piece suit – after all, back in the old days, British men would wear this cap with their workwear, casual wear, and best dress suit.
If you’re looking for a men’s hat that will see you through every season, the flat cap is definitely it. Just make sure the brim isn’t too wide; otherwise, you might end up looking like a member of the Addams family! Honestly, the best style inspiration I can recommend here is Thomas Shelby of Peaky Blinders fame. In this show, you can see him sporting this bad boy with everything from a dapper three-piece suit to a more relaxed getup.
#2 A Classic Beanie
As the colder days of fall set in, a classic beanie is my go-to when I want to look stylish and keep warm.
However, let me preface this by saying that I don’t advise wearing a beanie with anything but casual clothing. It’s strictly an informal hat and should never be worn with a suit!
That being said, when it comes to casual wear, the beanie can be a very versatile option. You can wear it slouched over your forehead or pulled down low so that only a hint of your hair is showing.
You can also experiment with different materials. A wool beanie will keep you warm in the winter months, while a cotton beanie is more suited to fall weather.
Whatever style you go for, just make sure that your beanie fits well. The last thing you want is an ill-fitting beanie making you look like a child!
When it comes to men’s stylish hats, the beanie is definitely one of my favorites. It’s comfortable, easy to wear, and can be styled in a variety of ways.
For the gents among you, try wearing your beanie with a pair of dark-wash jeans, a plain t-shirt, and a leather jacket. Trust me; women love the ‘bad boy’ aesthetic.
Attending a more sporty event? Not a problem – a beanie can easily be matched with a pair of sweats and a hoodie. Just make sure that your beanie isn’t too slouchy; otherwise, you might start to look like a teen in his mom’s basement!
Dad-bod style more your sort of thing? When it’s cold, a beanie hat’s your best friend while taking your kids to the park! Pair it with a chunky knit sweater, mid-blue jeans, and a pair of sneakers – you’re good to go!
#3 Baseball Cap
Hey batter, batter! Swing!
The humble baseball cap has fallen out of favor in recent year. For some unknown reason, a lot of guys have taken to wearing those chunky snap-back caps that increase the size of your head ten-fold.
I say ‘enough’. Let’s return to the good ol’ days of baseball cap-wearing dads supporting their kids at the local little league!
A baseball cap can be worn with just about anything – from a pair of shorts and a t-shirt to a tailored suit. However, as this hat has quite a sporty feel to it, I would advise avoiding pairing it with anything too formal.
If you’re attending a more casual event, such as a barbecue or outdoor festival, then the baseball cap is definitely the men’s hat for you. Just make sure that your cap is clean and free from any logos or branding; otherwise, you might end up looking like a walking advertisement!
One of my favorite styling tricks is to wear a baseball cap with an all-black outfit. Using your headwear as a statement piece isn’t conventional but can really make a statement if done correctly.
Alternatively, you can just wear your baseball cap with a casual weekend outfit. Jeans, a nice shirt, and a pair of white trainers might sound understated, but it’s a classic look that’ll never go out of style.
#4 Bowler Hat
I know this one’s a bit controversial, but hear me out.
Unfortunately, the trilby and fedora men’s hat styles have come to be associated with ‘neckbeards.’
In short, it’s a term used to describe a poorly groomed man who attempts to look stylish by wearing ‘classic’ men’s fashion pieces. Unfortunately, it doesn’t matter what you wear atop your head if you’re not looking after yourself, it can be hard to pull off anything remotely ‘stylish.’
As such, I’ve tried experimenting with other styles of men’s hats and came across the classic bowler hat.
In short, a bowler hat is a men’s hat that is typically made from felt or wool. It has a rounded crown and a brim that sits just above the browline.
The great thing about the bowler hat is that it can be worn with just about any smart-casual/formal outfit – whether you’re dressing up for a formal event or keeping things casual for a day out with friends.
If you’re feeling particularly daring, you could even try wearing your bowler hat with a pair of suspenders and a checked shirt. Sure, this might be classed as a bit ‘hipster’, but who’s to say you can’t push the boundaries of personal style once and a while?
A bowler hat is particularly flattering for those of you with epic beards. The soft, rounded shape of the bowler hat contrasts heavily with the facial hair – creating a look that is both stylish and unique.
#5 Trapper Hat
The trapper hat is probably the warmest hat ever invented. So it’s probably not ideal for the warmer side of fall.
However, as we move into the colder months, you can’t go wrong with the hat that originates from the chilled tundra of Siberia.
A trapper hat is easily identifiable by its furry ear-flaps that can be worn up or down, depending on how cold it is.
This men’s winter hat is typically made from a variety of different materials, including wool, leather, and fur. As such, it’s important to choose a trapper hat that is made from high-quality materials – otherwise, you might end up with a men’s hat that starts to fall apart after just a few wears.
When it comes to styling, the trapper hat can be worn with just about anything. However, as this men’s hat is quite bulky, I would suggest balancing the rest of your outfit with slightly chunkier items such as a chunky sweater or a pair of boots.
If you don’t want the rest of your outfit to look too bulky, then you could try wearing your trapper hat with a pair of slim jeans and a simple t-shirt. This men’s hat style is also great for those of you who wear glasses – as the ear-flaps will help to keep your glasses in place, even on the windiest of days!
So there you have it – five men’s hat styles that are sure to keep you looking stylish all autumn and winter long! Just remember to steer clear of any ‘hipster’ traps (see what I did there?) and you’ll be good.