The World of Vintage Mens Hats: How To Choose THE ONE

Updated on January 17, 2023 by

Man Wearing Vintage Mens Hats For Photoshoot

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Vintage mens hats are a timeless fashion accessory that can instantly elevate any look. Not only do they add an element of style and sophistication to any outfit, but they also offer protection from the elements and a unique vintage charm that can’t be found with modern hat designs.

Whether you’re looking for a classic fedora or more modern styles like trucker caps and baseball caps, there’s something for everyone when it comes to vintage mens hats.

In this article, we’ll explore why men’s vintage hats remain popular today, as well as some tips on how to choose the right one for your style.

We’ll also provide our top picks of some of the most iconic vintage mens hats available so you can get started on your journey to timeless style.


Benefits of Vintage Mens Hats


One of the most attractive aspects of vintage mens hats is their versatility. Whether you’re going for a classic, sophisticated look or something more contemporary and edgy, there’s sure to be a vintage hat that matches your style.

They also offer protection from the sun, wind, rain and snow, making them perfect for all kinds of weather conditions.

Finally, they can add an element of sophistication to any outfit and make it stand out in a crowd.


Tips on Choosing the Right Hat


When selecting a vintage mens hat, it’s important to consider its shape and size. The brim size should fit comfortably around your head, and the hat should be neither too tight nor too loose. You also want to make sure that the fabric or material of the hat matches with other items you’re wearing. For example, if you’re wearing a shirt and tie combo, then go for a more tailored hat look with a wool fedora.

Finally, consider choosing a vintage mens hat in a classic color like black or grey as these are timeless options that will look great no matter what season it is.

Whether you’re looking for the perfect finishing touch for your vintage look or just want to add a hint of timeless style to your everyday wardrobe, the world of vintage men’s hats can provide an array of options. From classic fedoras and flat caps to more daring pork pies and bowler hats, there is something out there for everyone.


Different Types of Vintage Mens Hats

Let’s explore some of the most popular types of vintage mens hats as well.




This iconic hat is often associated with old-fashioned charm and sophistication. The fedora has been a style staple since the 1880s and is still a popular choice today. Characterized by its wide brim and flat top, the fedora can be worn with a variety of looks from casual to formal.

Vintage Mens Hats - Fedora


Flat Cap


The flat cap, also known as a newsboy cap or driver’s cap, is another classic hat style that has been around for centuries. This style features a flat top with a short brim and often comes in tweed material. The flat cap is perfect for adding an old-world feel to your look and can be easily dressed up or down depending on the occasion.

Vintage Mens Hats - Flap Cap


Bowler Hat


The bowler hat is an iconic piece of menswear known for its distinctive round shape. Originally designed for British gamekeepers in the 1840s, this hat has since become a symbol of dandyism and rebelliousness. The bowler is perfect for adding a sophisticated edge to any look and can be worn both formally and casually.

Vintage Mens Hats - Bowler Hat


Pork Pie


The pork pie hat is a classic style with a unique rounded shape that sits low on the head. This hat looks great with casual attire like jeans and a t-shirt or paired with a dressier ensemble. It’s an excellent choice if you want to add some texture and interest to your outfit.

Vintage Mens Hats - Pork Pie




Whether you’re looking for something classic or something bold, vintage mens hats are sure to provide the perfect finishing touch for any look. From the timeless fedora to the daring pork pie, there is something out there for everyone.

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