10 Fashionable Vintage Fitted Hats You Need In Your Life

If you’re looking to stock up on some vintage headwear for your wardrobe, then finding some good vintage fitted hats is an excellent way to ensure that you have plenty of options when it comes to putting an outfit together. 

Vintage Fitted Hats

If you’re unfamiliar with fitted hats, a fitted hat is a type of hat that is designed to fit snugly on the head.

Fitted hats are often made of flexible materials, such as cotton or wool, which allow them to mold to the shape of the wearer’s head for a comfortable and secure fit (if your hat is a little too fitted, read how to stretch a hat out here).

Because they are sometimes not adjustable, fitted hats are typically available in a range of sizes to accommodate different head sizes.

So, if you’re looking for some of the best vintage fitted hats for your wardrobe, then hopefully this list will provide you with plenty of inspiration! 

Best Vintage Fitted Hats

Baseball Cap

The most recognizable fitted hat is definitely the baseball cap, and these hats are a type of fitted hat with a curved brim, which were initially worn by baseball players and fans, however, they soon became a massive fashion accessory! 

Baseball caps are typically made of cotton or another lightweight and breathable fabric, and have a hard, stiff brim that helps to shade the eyes from the sun, which is not only beneficial to the players that actually play, but for you as well.

The front of the baseball cap often bears the logo or emblem of a baseball team, and the back of the cap may have an adjustable strap or other fastening mechanisms that allows the wearer to adjust the fit. 

Baseball caps are one of the most popular forms of vintage fitted cap you will find, and are super popular because of the variety of colors you can find them in! 

Trucker Hat

Another popular vintage style of fitted hat is the trucker hat, which has seen a resurgence in popularity again in recent years.

For those who are unfamiliar with these hats, a trucker hat is a type of fitted hat that is typically made of a lightweight and breathable material, such as mesh or cotton and has a curved brim and a high, rounded crown. 

Although many people note that they tend to be similar in style to a baseball cap, the front of the hat often features a printed design or logo, while the back of the hat has a mesh panel that allows for ventilation. 

Trucker hats became popular in the United States in the 1970s and 1980s, and are often associated with the “trucker” culture of that era. So they make for a great vintage wardrobe accessory! 


If you’re looking for the perfect fitted hat for the colder weather, then a beanie is definitely the way to go. These fitted hats are designed to cover the head and ears for maximum warmth and comfort. 

In comparison to the cotton composition of most other hats, beanies are typically made of a soft and stretchy material, such as wool or acrylic, instead, and have a snug fit that helps to keep the head warm in cold weather. 

Beanies can be worn in a variety of styles, from slouchy and loose to tight and fitted, depending on the wearer’s preference. Some beanies may also feature a pom-pom or other decorative element on the top of the hat too! 

Cowboy Hats 

If you have a western-themed wardrobe, or you’re looking for a truly unique style of fitted hat, then why not opt for a cowboy hat? 

A cowboy hat is a particularly unique type of fitted hat that is typically associated with the cowboy culture of the American West.

These hats tend to be made of felt or straw, and have a wide brim that is designed to shade the face from the sun, which was definitely helpful for cowboys back in that era!

The crown of the cowboy hat is typically high and rounded and may feature a decorative band or other embellishments.

These hats used to be worn as a part of a cowboy’s everyday attire, and nowadays are more often used in rodeos and other western-themed events. 


Although they’re technically a type of baseball cap, many people differentiate snapbacks and baseball caps from one another.

These fitted hats feature a plastic snap closure on the back, allowing the wearer to adjust the fit of the hat, which is where the name “snapback” originates from.

Snapback hats are distinguished thanks to their flat brim and rounded crown, and they are often made from a combination of cotton and polyester.

Unlike other fitted hats, these hats have the ability to be adjusted to different sizes, which makes them more versatile! 

Bucket Hats 

If you’re looking for maximum sun protection from your fitted hat, then you should definitely consider trying to find a bucket hat.

These hats are typically made from a soft, flexible material such as cotton or polyester. 

They’re characterized by their wide, rounded crown and a brim that extends all the way around the hat. The brim is often slightly upturned, giving the hat a more casual appearance. 

Bucket hats are typically worn for casual occasions and are often associated with outdoor activities such as fishing or hiking, although their origins date back to their use in various military forces during the 1940s! 

5-Panel (Dad Hat) Hats 

More commonly known as a dad hat, a 5-panel hat is a type of fitted hat that features a rounded crown that is divided into five panels, rather than the traditional six panels. 

The front panel of these hats are typically made from a thicker, stiffer material, while the back panels are made from a softer, more flexible material. 5-panel hats often have a flat brim, and they are typically worn for casual occasions. 

These hats make up a large portion of the vintage hats you’ll come across, and with a variety of different colors, brands, materials, and designs, you’ll have plenty of options to choose from! 

Camp Hats 

Although they’re technically a form of 5-panel hat, Camp Hats are slightly different from dad hats, as they tend to be made out of a lighter, more breathable material that allows the wearer’s sweat to perspire out of the hat, rather than making their head sweaty.

However, it’s not unusual to see some winter variations of these hats made out of wool, with ear coverings too. 

As the name might suggest, these hats tend to be produced by outdoor clothing companies, but there’s still a chance they could pop up whilst you’re hunting for vintage hats! 


If you’re looking for a slightly more formal hat option, then a fedora might just be the type of fitted hat for you! 

These hats are a type of hat that features a soft, flexible brim and a rounded crown. It is typically made from felt or straw, and it is often adorned with a ribbon or hat band around the base of the crown. 

Although fedora hats were originally designed for men, they have also become popular among women as well.

They are typically worn for formal or semi-formal occasions, and they are often associated with a sophisticated or stylish appearance.

So, if your wardrobe consists of more formalwear than it does streetwear, then a fedora will likely make a much better fit! 

Panama Hats

Panama Hats

Another great vintage fitted hat option that is also suitable for semi-formal occasions is a Panama hat.

These hats were traditionally made from the plaited leaves of the jipijapa palm tree, which is native to Ecuador. 

Panama hats are known for their lightweight and breathable nature, making them a popular choice for hot weather.

They typically have a wide brim that is either rolled or flat, and a rounded crown that is often decorated with a ribbon or hat band.

Panama hats are often associated with a sophisticated or elegant style, and they are typically worn for formal or semi-formal occasions.

Where To Find Vintage Fitted Hats

So, where do you go if you’re looking to find some vintage fitted hats for your wardrobe? 

Well, the best place to look for vintage hats tends to be on online marketplaces, such as eBay, or Etsy, where people will likely have authentic vintage caps with various different details and colorations, which makes it much easier for you to find the exact hat you want. 

However, if you want to try to find your vintage hats in person, then checking through thrift shops and local flea markets is a great way to find some hidden vintage gems! 


We hope this guide to 10 of the most fashionable vintage fitted hats has been useful to you, and hopefully you now have some inspiration on what fitted hats would work for you and your wardrobe!

Willa Price

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