The Top 37 Best Men’s Hat Styles

Men’s hats are practical, functional, stylish, and a fantastic addition to your wardrobe. A hat not only looks good but it can also protect you from the elements such as sun, rain, and wind. They’re also great for hiding imperfections such as a bad hair day (or a no-hair day).

Just remember to not rely too much on your hat to make or break your outfit just in case you’re going somewhere that requires hats to be removed when inside. Keep reading for the best hat styles and outfit ideas sure to make your next “hat day” a smashing success!

1. Bucket

What goes around comes around… and apparently, bucket hats are no exception. First gaining popularity in the 90s and into the early 00s, the bucket hat is a way for the wearer to appear relaxed and chill (even if you are anything but) and add ease to any outfit. The flexible structure, easygoing aesthetic, and vast range of colors, prints, and textures also allow you to create your own individual statement.

2. Cap

Perhaps the most standard and basic of all the hats, this is one that will NEVER go out of style. I know they say ”never say never” but honestly, this is the most confident I have ever felt making such a bold statement. Whether you rock a dad hat, a vintage style, or one representing your favorite sports team, baseball caps are an easy, non-threatening way to top off any outfit, casual or dressy.

3. Classic

A classic hat can mean many things – baseball cap, fedora, and traveler’s hat to name a few – but what makes it classic is that they have been in style for decades. Sure, there are trends within these categories of hats but the basics are always classic and can be worn with almost anything. Daytime casual, dressed up for evening or even as a sun protector on the weekend. However you decide to rock these classic styles is up to you. 

4. Fedora

Oh, fedoras… This hat style is not for everyone, unlike most of the other hats on this list. A fedora definitely takes a special type of gentleman and wardrobe choice to be able to pull it off. First gaining popularity in the 20s by being worn on the heads of gangsters, detectives, and journalists, they tend to be seen on men who fancy themselves to be a “hipster” or “old-fashioned,” but don’t let that stop you. Just know that if you want to venture into the world of fedoras, I will support you (even if no one else will…)

5. Flat

The flat cap goes by many other names: ivy cap, gatsby, driving cap, newsboy, and duckbill to name a few. Despite what you decide to call it, the flat cap is easier to pull off than a fedora and tends to look better with a suit. They still have an old-fashioned feel but seem to be more widely seen than the classic fedora.

6. Leather

Leather is a great material for hats because not only is it breathable but it’s also extremely durable. Available in an array of styles, leather can be worn and pulled off by everyone, including, but not limited to Indiana Jones; and he’s obviously a badass so you’re in good hands with leather, regardless of the style.

More good news! Leather tends to work with just about every outfit and colorway so feel free to get dressed for the day and just throw your new hat on your head as you walk out the door. No forethought required.

7. Panama

Throughout history, people from all walks of life, including presidents, artists, politicians, and celebrities have worn, and continue to wear, Panama hats. Fun Fact: Panama hats are not actually made in Panama but are actually hand-woven in Ecuador. 

Creating a Panama hat includes over 30 steps, from the selection and harvest of the toquilla straw to the tightness of the weave. They became known as Panama hats due to their massive export from Ecuador to Panama during the construction of the Panama Canal during the 19th century. Styling-wise, my two favorite looks are Riviera style with a linen suit as well as a more casual beach look complete with shorts and a Hawaiian shirt.

8. Safari

From a practical and literal perspective, there are three requirements for a proper safari hat: One – a safari hat must provide complete coverage from the sun including all-around shielding, especially in the back of the neck area, which tends to be left out of most hats. Second, the hat should allow your heat to breathe and not trap heat. And last but not least, they should be water-absorbent on the inside and waterproof on the outside. 

Styling a safari hat tends to work better with a casual outfit. Think of a long day outside at the park or hiking through the woods. A safari hat is more practical than stylish, per se, but with all the various fabrics and patterns, I will freely take back that last statement if you can prove me wrong.

9. Vintage

Many of the hat styles above are considered vintage, such as the fedora, flat hats, and even Panama hats. Technically a hat is vintage when it is at least 15 years old but you can get away with a new hat in a vintage style.

Fabrics also play into a hat being vintage such as being faded, perhaps with a little wear and tear and even certain colorways. That being said, hold on to your hats and pass them down so the next generation can relive your glory days just as you are with someone else’s classic vintage cap.

Hopefully, you now have a better understanding of different hats and ways to style them. The biggest advice I have is to just do what feels right and be you, regardless of what is considered “trendy” or “fashionable.” Being yourself and being confident is your biggest advantage to pulling off any of these looks.

10. Western

Surprisingly (to me anyway) there is a variety of western hat styles – the derby, the pinched front, the gambler, and the cattleman – each with their own unique features. The best way to decide which one is right for you? Try them all! And don’t worry if you’re a city boy. Did you know that John Stetson (the originator of the famous Stetson cowboy hat) was born in New Jersey, not out on the farms in Oklahoma or in Texas, which would have been my guess. 

These hats are available in different fabrics, embellishments, and sizes. As far as styling goes, you can’t go wrong with a plain white t-shirt and jeans. Solids, plaids, flannels, and sweaters also work. Just try to avoid anything that screams “COWBOY!” Unless that’s what you are going for or are headed to a costume party.

11. Winter

Beanies, also called stocking caps or sock hats, are the most common winter hats because they are the most casual, practical, and versatile. Made for colder weather, beanies are also a favorite amongst anyone looking to just throw on an easy hat. I wouldn’t suggest throwing one on in the heat of summer but I’ve seen it before and didn’t bat an eye. 

Flat caps are also a great winter hat option because they tend to be made from wool and felt and help keep your head warm. Along that same theory, as long as a hat is made of a material with a tighter weave and protects your ears from the harsh realities of the cold, you may refer to it as a winter hat.

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