How to Wear a Hat with Style & Confidence – 7 Tips to Look Great in Men’s Hat


While hats were once a requirement for any man in a public setting, societal changes through the 20th and into the 21st century have now made hats entirely optional in all but the most niche of settings. Today, we discuss wearing classic hat styles as a modern man and how to do so confidently and stylishly. 

This post is the first of a two-parter on hats. The second part will cover the surprisingly easy and simple process of reshaping a felt hat at home.

The Fall of the Hat-Wearing Tradition

Many attribute the decline in hat-wearing, particularly in the US, to the presidency of John F. Kennedy–a man who was known for his good looks, including his hair.

The story goes that when JFK went hatless to his presidential inauguration in 1961, sales of hats across the country dropped precipitously. While this story has been repeated in print and elsewhere many times, the fact of the matter is it actually isn’t true. In fact, JFK actually revived a hat-wearing tradition at the inauguration.

JFK in morning dress with a top hat

While President Harry Truman, a former haberdasher himself, wore the customary top hat to his inauguration in 1949, his successor Dwight D. Eisenhower chose to wear the slightly less formal homburg to his inauguration in 1953. When he did so, Truman also wore a homburg that day as a show of good faith.

JFK did have a top hat at his inauguration, and that was well covered. It just so happened that for reporters and cameras to see his face better during the inaugural speech itself, he wasn’t wearing the hat at that time.

When Did the Cultural Shift Against Hats Really Begin?

It can probably be traced to the end of World War II when returning servicemen were so sick of wearing things on their heads like helmets or their uniform headwear that they stopped wearing hats more and more in civilian life as well.

Whatever the historical case for the decline in hats may be, we’ve begun to see a bit of a hat renaissance in the last 15 years or so. This can probably be attributed in part to stylish television shows like Mad Men and Boardwalk Empire, where hats are depicted regularly. More and more modern men are again starting to see the virtues that a classic hat can provide.

Nucky Thompson from Boardwalk Empire (Image credit: HBO)

But if you’ve never worn a traditionally styled hat before, you may be worried that if you try to wear one now, you’d look silly, unconfident, or out of place. We’re happy to say, though, that this doesn’t have to be the case. Let’s run down some tips to stylishly wear hats in this day and age.

7 Tips to Look Great in Classic Men’s Hats

If you’re looking to transition more often from ball caps and beanies to more classically styled hats, we’ve got seven tips today on how you can do so effectively.

1. Find a hat style that complements your face shape

Not all hats are created equal, of course, and as we’ve said, there are many different styles, so you’ll likely want to try on many different shapes and sizes of hats to see which one harmonizes best with your natural proportions. Since a hat naturally sits so close to your face, it will draw the eyes almost immediately.

Find a style that complements your face shape.

Therefore, finding a hat that works well with your face shape is definitely important. Of course, be sure to learn your hat size as well. This is especially important if you’d like to wear a stiffer hat style like a homburg, bowler, or straw boater. These hats aren’t going to stretch and conform to the shape of your head as much, like flat caps and some fedoras will.

2. Make sure that your chosen hat complements your skin tone

Once you’ve found a style or, indeed, styles of hat that you would like to purchase, the next big consideration is probably going to be what colors you want to get. One important consideration when contemplating color is choosing a hue that harmonizes well with your skin tone. Since the hat is, again, closer to your face than some of the other elements of your outfit, this isn’t an insignificant concern.

For men with pale and or lighter skin tones, darker colors like charcoal and medium gray, dark to medium brown, and navy blue are best. In other words, the menswear staples will contrast with your skin and bring warmth and color. For a more adventurous and fashion-forward look, you could try something like burgundy or perhaps dark green.

Best hat colors for pale and lighter skin tone.

If you’ve got a more olive skin tone, your slightly warmer complexion will benefit from colors that are either slightly brighter or darker than the middle ground. For example, you could take a mustard brown trilby. Lighter grays will work here as well, and the bold can experiment with more different types of colors.

If you’ve got a darker skin tone, we’ve got good news here: you can pretty much wear any color you’d like but try to keep some contrast between your skin color and the color of the hat.

Hat colors that are either slightly brighter or darker than the middle ground will work best on someone with an olive skin tone.

One shade that we would advise wearing only sparingly, however, is black. It’s probably going to wash out a lot of skin tones, and it won’t harmonize well with many outfits. Black hats are best worn only with more formal dress codes like black homburgs for Black Tie and black silk top hats for white tie. Even morning dress will often substitute a gray top hat for a black one.

3. The hat color you choose must harmonize with your outfit

After considering your skin tone then, our third tip is to keep in mind how the color of the hat you’ve chosen will harmonize with the other colors in your outfit. For example, if your outfit features browns and blues, a brown hat would be a safe bet, while a blue hat could work but would be perhaps a bit more daring. If you’re wearing an outfit that has many grays, a grey hat is obviously going to work well.

Outfits mostly in blue can work equally well with a brown or a gray hat depending somewhat on the colors of your accessories and leather goods. That is to say, if you’re wearing mostly brown leathers, go for a brown hat, and if you’re wearing black leathers, go for a gray hat.

Choose a hat color that complements the other colors in your outfit.

As a personal example, the two hats in my own collection that I wear most often, at least outside of the summer months, are trilbys in charcoal gray and mustard brown. They pair well with almost any outfit, and they don’t overpower it.

In the winter, don’t forget to consider how your hat will pair together with your outerwear, not just your overcoat but also your gloves and scarves. The techniques for pairing these accessories together well covered in our How To Pair Overcoats with Gloves and Scarves can also be extended to hats. The exception to these points about harmony lies chiefly in the realm of summer hats.

A selection of straw boaters, each with a multicolored, striped band.

Warm weather hat styles, with the partial exception of the straw boater, are generally considered less formal overall and are less of a finishing touch to your outfit as they are a practical accessory. As such, you don’t really have to worry if your summer hat is paired quite so exactly to the rest of your outfit with the possible exception of a straw boater, which, again, is more formal than other summer hat styles. So, in the warmer seasons, have fun and experiment.

4. Pay attention to the weather

Transitioning, then, from seasons, our next tip is to pay attention to the weather. Remember that a hat isn’t a purely stylish accessory. It can also serve a direct function.

In the summer or on any sunny day, a traditional hat style with a brim can help keep the sun out of your eyes. Hats can also keep your head from getting wet in the rain when you’ve forgotten your umbrella, though we wouldn’t really recommend getting them soaked. And they can also help keep snow off in the winter.

A nice straw hat for the summer.

Also, whether it’s a straw hat in spring or summer or a felt hat in fall or winter, hats can work to regulate your body temperature keeping your head cool or warm as desired. With that said then, keep in mind that certain materials look best and perform best in certain seasons.

Felt and other wool hat styles are the safest choices for autumn and winter, where they can also be supplemented with ear warmers in the latter case, and they can also work on cooler days in the spring.

Felt and wool hat styles are best during the winter seasons.

Meanwhile, straw hats are best worn exclusively in summer though they can be worn on warmer and sunnier days in the spring. These aren’t absolute rules, of course, just general guidelines to keep in mind.

5. Be mindful of the overall formality of your outfit

Certain hat styles are more formal than others and thus, can affect your outfit accordingly. Generally speaking then, the stiffer a hat style is, the more formal it is. The prime example of this would be the top hat, which is a quite stiff hat sized specifically to one’s head using a specific machine and is also worn with only the most formal of dress codes–White Tie and morning dress.

Down one step in both stiffness and formality would be the homburg worn with Black Tie and stroller suits, the bowler or derby also worn with strollers and suits, and the straw boater worn with warm-weather black tie and formal summer looks.

A top hat is only worn with morning dress or white tie events.

Next would be fedoras, trilbys, and pork pie hats good for business attire and some smart casual outfits, followed by flat caps and panel caps, which are good for smart casual and casual looks, especially in the fall.

Of course, there are many other hat styles that we didn’t mention here but in general, remember that the stiffness of a hat can be used as an indicator of its formality and make sure that the hat is similarly formal to the rest of the outfit you’re wearing.

6. Be mindful of hat etiquette

This is another point that we won’t spend a great deal of time on today as it has its post, but suffice it to say, if you’re confident in your knowledge of traditional hat etiquette, which should still be observed, at least to some degree when wearing traditional hat styles, then you’ll be that much more confident with the hat in the ensemble.

Be mindful of wearing a hat in public and private places.

As a general rule, your hat should be on in public spaces and off in private spaces, but be sure to read our Hat Etiquette Guide as there’s a lot more nuanced than that.

A Note on Hat Hair

One of the upsides of maintaining a traditional hairstyle as Raphael and I do, or an otherwise close-cropped style like Kyle does, is that you won’t have to worry about a traditional style of hat mussing up your hair. So long as you put on and take off your hat properly using two hands, your hair should never need more than a quick touch-up and often won’t be disturbed at all.

Remove your hat properly with two hands so your hair won’t need a touch-up.

In fact, I sometimes use a battered old trilby, which I refer to as my hair hat, to hold things in place in the middle of styling. Traditional hats can work with more modern, which is to say, longer hairstyles, but the hair will likely have to be swept out of the face or otherwise held back.

7. General Hat Style Tips

Our final tip here is a set of general style pointers. Hopefully, all of our preceding points have been building your confidence.

If you’re still a little bit wary, try to keep all of them in mind, and also, consider wearing a more minimalistic look overall. That is to say, think about keeping the rest of your accessories and outfit details pretty basic. Especially for a new hat wearer, a hat can carry some weight both because you might feel some comments and compliments from others and because you might feel a bit self-conscious, which will be communicated in the way you carry yourself.

A simple yet stylish look.

Going with a simpler look using staple colors, neutrals, and maybe even a monochromatic feel will free up your mental energies to making sure that your hat looks good and you’re following the other considerations we outlined today.

Overall, remember the old saying that “You should wear the hat. The hat shouldn’t wear you.”


Finally, here’s a piece of good news: while the evidence isn’t exactly scientific, history and aesthetics tell us that wearing a hat can actually make you more confident because a hat will often make you look taller.

Wearing a hat adds confidence as it makes you look taller.

It can, therefore, send a subconscious signal of increased strength or power. This is evidenced by the fact that many police and military dress uniforms often feature a hat, as did many other types of uniforms in past centuries. So, let this confidence spur you on to more hat wearing. Combine it with all of the tips that we laid out today, and you’ll be well on your way to making classic hats a staple of your wardrobe.

What’s your favorite classic men’s hat, and how do you style it without looking dated? Let us know your techniques in the comments section!
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