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When is it Good to Wear a Fedora Hat? What Events/Occasions?

August 5, 2021February 25, 2025 Accessories
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A woman wearing gray clothes and a gray fedora at the park.

I went to a pub with my friends last weekend. Now, I’m not used to seeing people wear hats indoors for the most part, especially since I rarely went anyplace fancy and my family had an old-fashioned view when it came to taking hats off indoors. There were several men around the place wearing a certain type of hat with a short brim that I could recall from movies but didn’t know what it was called.

I asked the buddy closest to me, “What is this hat that all these guys have on? Is this some kind of trend I don’t know about?”

She smirked, laughed a bit, then answered, “It’s known as a fedora! I would think you being such a cultured person, you’d be familiar with them.”

No, sorry, I guess I’m not as hip as I previously thought. I decided that when I got home, I’d immediately do some research to find out more about this type of medium brim hat. I sure learned a lot in my research! 

Anyway, here is some of what I’ve learned about this fascinating head adornment. 

FYI, thanks to AI imagery software, we’re able to create very specific fashion examples to illustrate the points being made.

What is a fedora? 

A fedora, simply put, is a hat that features a flexible design and a short or medium brim that can protect its wearer from rain. It also has three “dimples” on it, with two on the sides and one on top. Another way that people describe it is that it has an “indented crown.”

Some of them come with a ribbon surrounding the base of the hat, which is thought to be quite fashionable. 

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When is it good to wear a fedora hat?

This is a woman staying at the al fresco section of the restaurant wearing a fedora.

You’ll find that a fedora tends to be more of formal use. Regardless, many cultural niches have made use of this and adapted it with their own versions. For instance, there are great designers of urban wear who have designed fedoras. 

Fedoras are best when worn during the slightly cooler months, as well as on days in which the weather is a bit cooler. If you’d like to keep with this style when it’s hot out, opt for a Panama hat. This way, you can get the feel of having one on while having more ventilation and wearing something that’s more lightweight. 

The occasions where you’d include a fedora hat in your outfit are numerous. For instance, you might wear one while attending a wedding. This makes for a snappy accessory while you’re wearing formal slacks and a dress shirt.

The same is true when you’re attending an upscale dance/ball. There’s a certain mystique to an individual who wears a fedora hat and it’s an ideal way to dress up your ordinary suit or dress clothes with a tie. Many people wear fedoras to black-tie events for a bit of a unique look.

You can play up a more casual outfit when you’re in an outdoor setting if you opt for a straw fedora. If you’ll be going to the Kentucky Derby, you may be in good company if you wear this hat. 

What is the history of the fedora hat? 

A close look at a man wearing a fedora and trench coat.

This medium brim type of hat started out as a part of men’s fashion in the first half of the 20th century. They only grew in popularity when they were used often in the gangster scene, particularly with people who were involved in going against the prohibition movement. 

The fedora stopped being as popular in the middle of the 20th century. However, when the artistic and cultural movement came about later in the century, there was a revival of people who wanted to wear this hat. Stars such as Humphrey Bogart and Frank Sinatra could be seen with these hats on frequently.

It also was a staple of Indiana Jones’s costume in the famous movies named after this main character. 

In the late 20th century, we saw a resurgence of fame with Michael Jackson and other well-known musicians and other famous people wearing fedoras. In the general public, not only men made it a part of their wardrobe! It’s truly become a part of gender-bending fashion to put one of these hats on. It’s no longer considered just a “men’s hat.”

This type of hat is especially popular in indie, bohemian, and urban scenes.

Where can you buy fedoras? 

A close look at a bunch of fedoras for sale.

Fedoras can not only be purchased at hat shops, they also can be found at department stores, boutiques, and from a variety of online stores. You’d be pleased to see just how many places are selling these stylish hats today. From bargain shops to more upscale outfitters, you definitely have your wide pick of options from which you can shop for a fedora hat.

Some of the more commonly known places to buy them include Target, Kohl’s, Macy’s, Walmart, and the Stetson company. 

FAQs About Fedoras 

How do the fedora get its name? 

Even though the fedora was originally a hat worn by predominantly men, the name derives from the princess “Fedora” in the 1882 play written by Victorien Sardou. Its lead character wears this felt accessory, which then was noticed by the audience, who were mostly male. 

You may come across another name when looking up this hat – Borsalino. Giuseppe Borsalino, who ran an Italian luxury hat company, included the hat in a number of his lines and turned it into one of his star accessories. 

Should you wear a fedora with casual clothing? 

Typically, no it’s not a good idea to do this. That’s because fedoras have become famous for their use in certain settings and seen on gangsters in the old movies. They lend a polished look to a suit or other types of dress clothes. 

However, you should know that this is a rule that can be broken. Pair this short brim hat with the right pair of jeans, nice shirt, and a blazer, and you’re golden. You might even set a trend in your area if this isn’t something that happens often.

All in all, it’s a stylish piece that can work well with many types of clothing as long as you put care into the other aspects of the outfit. 

How do you wear a fedora in the correct way? 

First, you need to make sure that your hat fits on your head properly. Make sure that it’s not too large and that it doesn’t droop onto your forehead at all. The best fit is when it rests just about the center of your forehead and above your ears comfortably.

You might tilt it to the side a little if you like this look. This doesn’t suit everyone, and the most common way to wear this hat is to have it centered and straight. As long as you’re comfortable and confident with how you’re donning your fedora hat, that’s the most important thing.

What types of fedoras are there? How can you choose the right one for you? 

There are a ton of varieties of fedoras. Materials that they’re made out of include felt hat, straw hat, and wool. The kind you should buy and wear depends on what you’ll be wearing, what your hat style is, the climate where you live or where you’ll use it, the occasion, and several other factors.

Consider what will have you feeling and looking your best. If you only plan on buying one, it’s crucial that you get something you can use in different settings and for different types of events. 

When you’re in a warmer climate or if it’s an especially hot summer, it’s ideal to have a straw fedora hat to prevent yourself from overheating. Conversely, the colder climates and months require that you wear a wool fedora to ward off the chill. 

Another option that might not be so common is a leather fedora. This is typically worn with urban styles of clothing. It’s definitely a bold choice so it’s not really the best choice for everyday wear. 

A great way to decide which fedora you should go with is to search reviews, look up their pros and cons, and think about the instances when you’d most likely put on your fedora hat. You also could visit a store (or a few) and try on some of the collection that’s available if the staff allows you to do so. Most have mirrors and dressing rooms for this very purpose, and a knowledgeable salesperson can even assist you since they are certain to have a great deal of experience with fedoras. 

Would you do well with something that is more like a cowboy hat or Panama hat? Fedoras are a similar style of hat and they are well-suited to all kinds of settings and occasions. You’ll want to think about how much you’re willing to spend, the color of hat that most will accentuate your wardrobe as well as what may be requested of you if there’s a particular color scheme at the wedding, dance, or other event you plan to attend. 

Do you tend to like shopping with other people? It may help to bring along a friend who can assess the choices and give you feedback on what looks great on you and which are duds. You’ll love having another set of eyes to make this process a little easier and it even can be fun to shop from these fashionable hats with someone you trust to be honest and helpful.

Is it common to wear a fedora if you’re a woman? 

Today, the fedora has its place among women’s hats. Though it historically was worn by men, women now love this accessory and there are specific fedoras that have been designed for women’s wear. Regardless of who you are and what your background is, it’s possible for you to bring this hat into your wardrobe and use it to accentuate your own unique style. 

How does wearing a fedora make you feel?

Whether you wear a black fedora, cocktail hat, boater hat, bowler hat, or some other variation on this style, it’s a way to boost your image a bit and show more confidence. There’s a saying that you should dress how you feel, but the opposite is just as true – if you’re feeling down or need something to improve your confidence level, a designer hat in the form of a fedora is sure to be a worthy choice.

You can pair it with jeans, formal slacks, a maxi dress, or a jumpsuit, among other clothing options. Stay true to yourself and try out a wide brim hat to see if it is to your liking.

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