Written by Rakelle Maurici in Tips & Advice on the 16th July 2015

Photography by Craig Landale

In recent years we have seen an increase in hats of different styles that were once popular. With the rise of musicians, actors and other celebrities influencing headwear, we take a look at which styles we should be wearing. We’ve now moved on from the regular baseball cap and with the return of the fedora and panama, there is a hat for almost any occasion.

Fedora 

The gangster hat. The fedora was a popular hat in the 1920s and 1950s and made popular by the likes of Al Pacino, Frank Sinatra and the mafia gangs - hence it’s thug like stigma. Generally fedoras are felt or straw and dented lengthwise and pinched at the front with a sturdy and flexible brim so it can be snapped up or down. Typically they are worn at a slight tilt and askew. A fedora looks good with a three piece suit and typically double breasted during winter with an overcoat. Brands such as Borsalino make the best of the best Fedoras in a range of colours and sizes.

Pork Pie 

The name really comes from the shape of the hat; it looks like a pork pie dish. The brim is narrower than a fedora and turned up at the edges the whole way around and flat on the top. The stiffer the hat for this style the better. Generally speaking, this style hat has been named as the "hipster hat" in recent years - with the rise of the beard, it has been a common sight to see a tattooed guy with a leather jacket wondering the streets of Shoreditch in a pork pie hat. Needless to say they are still great to wear for a formal affair with a slim fitting suit and monk strap shoes for a modern twist.

Homburg 

Often described as the dressiest hat of all, made in either felt or straw. The brim is generally stiffer than a fedora as it is not made to be snapped up or down as the edge is upturned the whole way round which makes the style dressier as it cannot be moulded. So this is the perfect hat for an evening event or a wedding if you want to go the extra mile on accessorising.

Trilby 

A slightly more casual side of smart hats - they have a short and narrow brim which is angled down at the front and turned up at the back with a slightly shorter crown so it’s smaller overall. These can be felt and straw again, and are more commonly worn during the summer months (something we saw a lot of at festivals a few years back). These were really popular back in the 1960s and 70s until they became seen as a nerdy look during the 80s and 90s. Nonetheless this stigma has since gone and now they look a little more preppy - so this style looks great with casual shirts and shorts with boat shoes.

Boater 

A summer formal hat. You will only see a boater made from stiff straw (the name is kind of a giveaway) and the top is flat with a wide brim and wide band; usually coloured. It’s the kind of hat you once saw at summer weddings and boating regattas. The perfect style to wear with a summer blazer and smart three-piece suit.

Newsboy 

The newsboy or sometimes called the "working man’s hat" as they were once commonly worn by lower class citizens, bandits and artist... think Oliver Twist! It's a casual style hat to be worn with jeans, boots, an oxford shirt and a casual blazer. However, recent trends would allow you to incorporate casual styles with smarter ones, so you could style this type of hat with a slim fitting suit if you want a modern tailored look.

Baseball 

Sometimes seen as a little "immature" or a hat for just teenagers but baseball caps are just as much stylish as they are practical. For casual days when you want to cover your hair or if you're heading to the gym, this hat will look cool and effortless - just leave the snapback with the stickers at home.

Beanie 

The simplest of hats, it’s there to keep you warm and it actually does. Usually made from wool or cashmere to keep the warmth in and the cold air out. Again, like the more casual styles of hats we are seeing them styled with tailored outfits - just remember to keep your outfit simple so it doesn't look like you're trying to be different. It's simple to decorate hats with patches and add a personal touch. A custom embroidered patch is an extremely popular choice because it is easy to apply and comes in a wide variety of styles. The best way to find something you will love is to come up with your own design or have a patch made exclusively for you. You can make the custom embroidered patches that feature teams, sports, logos, animals, symbols, and more. It’s a great way to show your personality and what you love. 

Panama 

A popular Ecuadorian brimmed straw hat we see during summer. There are lots of variations in terms of colour but the most popular is your regular white/beige straw made from a palm like plant. To own a decent Panama hat you'll need to invest in a good one, simply for the fact that if the straw is not of good quality they are stiff and uncomfortable. The style is similar to that of a trilby; the brim comes down at the front and it curls up at the back. Unfortunately, authentic Panama hats are almost becoming extinct in Ecuador, but there are many brands out there that make quality Panama hats such as Nick Fouquet and Borsalino.

We list many of the different types of men's hat designs in this Guide to Men’s Hats with street style photography examples.