Men’s Guide On Looking Great Wearing A Hat

Men's Guide On Looking Great Wearing A Hat

According to Gentleman’s Gazette, hats were a common sight until the 1920s.

There is no doubt that the practice of wearing hats has declined considerably over the years, especially in America. Many people attribute this phenomenon to John F. Kennedy, a former president of America who was so good-looking that he even went without a hat to his presidential inauguration, causing the sales of hats to plummet.

However, despite this story becoming immensely popular in the media, it is unfortunately not true as the president did wear a hat on that famous occasion like many other presidents before him.

The story perhaps did the rounds because Kennedy delivered his address without his hat on so the photographers could get better shots of his face.

According to many historians, the cultural shift against the practice of wearing hats began after World War II ended because the soldiers were fed up with their headgear as part of their uniforms, and discarded it in their civilian lives.

The Return Of The Hat 

However, on a heartening note to many gentlemen of refinement, hats have been making a comeback in the last decade and a half, possibly due to the influence of several popular shows on TV.

However, in the meantime, many men had forgotten the art of wearing a hat stylishly, while others had never worn one. As a result, they fear that they would look out of place, silly, or gauche wearing a hat on formal occasions.

However, the good thing is that looking fashionable in a hat is not rocket science as long as you keep a few tips in mind.

How To Look Confident & Stylish Wearing A Classic Hat

picture of a beige colored hat lying on the grass in a garden with flowers on it as decoration.

1. Identify a hat style that complements your face:

The good and the bad thing about hats is you get them in many shapes and styles, and it is easy to be overwhelmed when choosing a hat. The best way is to try on as many as you can find to find one that you like the look of and one you look the best in. Seeking the advice of an experienced hatter or a friend can help.

A hat draws the eyes to it immediately because it sits very close to your face, which is the reason, you must take the trouble to find a hat that goes well with your face.

Another important factor you must get right is the hat size, especially when buying a stiff hat style like a bowler, homburg, or straw boater because stiff hats do not stretch and adjust to the size of your head like fedoras and flat caps.

2. Pick a color that matches your skin tone:

The next step after you have found a hat style you look good in is to choose the color. While you can nowadays get hats in varied colors, you must get one that goes well with your skin tone.

Remember your face is closer to the hat than your clothes. Colors like dark to medium brown, charcoal, medium gray, navy blue, etc., generally work best if your skin tone is light or pale. The point is to choose a color that will provide a good contrast with skin tone and lend it color and warmth, says an owner of a business dealing in wholesale fedora hats.

If your skin tone is warmer, you will benefit from darker or brighter colors, like mustard or light gray. You can wear a hat in any color you like if you have a dark skin tone as long as there is sufficient contrast between the hat color and the skin tone.

Even though black is a common color, you should probably avoid it unless you are going to an occasion with a strict and formal dress code since black tends to wash out many skin tones.

3. Harmonize the hat color with your outfit:

You must also pay attention to the outfit color to ensure the hat harmonizes well with it and adds to the total impact. If you want to play it safe, you can choose a complementary color, for example, a brown hat with a brown suit, but if you want to be bolder, you can opt for blue instead.

If you are wearing a blue outfit, you can safely wear a gray or a brown hat, depending on the color of your accessories like shoes and belt. A gray hat goes well if your suit is predominantly gray. You may need to buy two hats, one in gray and the other in brown, for more flexibility with your outfits.

For hats you want to wear in winter, you need to consider the color of your overcoat, scarf, and gloves for the best result. Generally, you can be more adventurous with colors when wearing summer hats.

4. Consider the weather:

One of the biggest factors in choosing a hat is the weather. You must remember while a hat is a great style accessory and one of the best men’s fashion trends, it also has a more direct function of keeping you protected from the sun or the cold.

When stepping out on a sunny day, you will do well to wear a wide-brim straw hat to keep your head cooler and lighter, while a felt or fur hat will work wonders to keep you warm on a cold winter day. In some places, it never gets so cold that you need to wear a warm hat.


In addition to the considerations discussed above, one of the main factors in choosing a hat is how formal or casual the occasion is. You would not want to look out of place wearing a casual summer hat at a funeral or a church service while wearing a bowler hat at the beach would raise eyebrows.

Generally, stiff hats do better on formal occasions, while those with soft crowns and floppy brims suit casual occasions better.

For example, you will do well to wear a top hat, a homburg, or a bowler hat with a suit, while a straw boater or a cowboy hat can look great with a pair of jeans and a check shirt. Flat and panel caps suit casual occasions better.


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