10 Fashionable Vintage Hats You Need In Your Life

We all know how well a hat really caps off an outfit (to pardon the pun).

Sometimes all you need to make that waistcoat match with those cords or that skirt to match that blouse is a really decent vintage hat.

10 Fashionable Vintage Hats You Need In Your Life

However, what hat should you match your outfit? The thing about vintage hats is that there are so many of them (for something more fitted, check out our favorite vintage fitted hats). From baseball caps to fedoras, there are plenty of old skool hats that will match your old skool style.

So, what types of vintage hats are available for you?

What materials are they made from? How do different types of material match? Well, let’s have a look at different types of hats so you can get a better idea of what you’ll need.

Why Does A Hat Make An Outfit?

One of the great things about hats is that they convey authority. If you are wearing a vintage hat, people will automatically think that you know what you’re doing.

Also, sometimes vintage clothing will not match anything modern. If you are wearing cords, then you might not want to wear modern sneakers, for example.

Therefore, having a certain uniformity in your outfit will be very important.

Hats are also a great source of comfort. If you are walking through a cold climate regularly, then you might want a hat to trap all the heat from the top of your head.

So, this might be the reason to wear a vintage hat, but what vintage hat will you need for your outfit? Well, we’ve scoured the internet to look for some of the very best. No doubt you’ll find done that will fit in with your outfit.

Best Vintage Hats

1. Fedoras

Vintage Hats - Fedora

This kind of brimmed hat will make you look like a detective. They are made from a whole host of different materials, from wool to felt.

You’ll definitely be able to find something that will match your clothing choices.

Also, the great thing about this style of hat is that they are not gendered, even though they look like distinctly male hats.

Women can use this accessory to create that vintage David Bowie Young Americans-era look.

2. Newsboy Cap

Vintage Hats - Newsboy Cap

If you have ever watched Peaky Blinders, then you’ll have seen this kind of baggy peaked cap.

This comes made from a whole host of different materials, from herringbone to regular felt. This will work really well with a plain shirt and tie combination.

This type of cap is also very comfortable, especially if you get it in wool.

It is easy to machine wash too, although we would recommend that you hand wash it so that you don’t ruin the fibers.

You could also match this with a wool waistcoat for a great gentleman rascal effect.

3. Trilby

Vintage Hats - Trilby

In a similar vein to the fedora, this has a slightly smaller brim with a much more pronounced bowl. You can wear this one with a suit or go plain white shirt and braces for that pub rocker type of look.

This hat can be worn by men or women and come in many different materials, including felt, wool and even straw. This latter one is usually very cheap to buy and is the perfect accessory for the summer season.

4. Baseball Cap

Vintage Hats - Baseball Cap

If you fancy that much more low-key look, then we would certainly suggest getting a vintage baseball cap.

You can gain the respect of the most die-hard sports aficionados by picking up a baseball cap featuring the insignia of your favorite team.

A baseball cap is usually made for casual wear, so most likely you’ll be wearing a vintage T-shirt with some ripped jeans.

This is great if you are going on a first date and want to appear casual yet, on closer inspection, it’s obvious that you’ve put in a lot of effort.

5. Plaid Newsboy Cap

Vintage Hats - Plaid Newsboy Cap

This is a very distinct category all by itself. These caps project an air of authority and will be great if you want to adopt that formal vintage look.

These caps are extremely durable, which is great if you want something that is going to last.

This type of cap will go very well with combinations of check and plain cotton designs.

We would recommend this type of cap to top off a three-piece suit. This cap goes very well with some plain brown shoes too.

6. Straw Fedoras

Vintage Hats - Straw Fedoras

During the summer season, finding the right vintage hat might be hard to come by.

This is because a lot of the styles that we have listed above are made from thick material like wool or felt, which will be very uncomfortable to wear in warmer weather.

That is where the straw fedora will come in. These usually come in a cream style that will match lighter summer clothes and materials like linen.

These hats are also very breathable, helping you to keep your head cool and sweat-free.

7. Boaters

Vintage Hats - Boaters

This is another hat that is made from straw (although you can get hats that are made from synthetic materials), which makes it very breathable and easy to wear.

This is a classic vintage hat and will cultivate that ‘idling by the river in 1920’s Cambridge’ look.

If you are a fan of sophistication during the summer seasons, then we would certainly recommend that you get a boater. These hats are very durable and stylish, which is great if you want to buy one hat to last you the whole summer.

8. Mushroom Hats

Vintage Hats - Mushroom Hats

This one is mainly for women, coming in a huge brim that hangs down over the shoulders in a way that suggests the wearer is demure and mysterious.

This is a great hat to wear to a gala or an upmarket wine-tasting event.

This hat comes in a wide range of different materials, although the main one is either wicker or felt.

This type of hat is perfect for the winter as it will give you a lot of coverage. This would be ideal for wearing with an off-the-shoulder dress.

9. Pillbox

Vintage Hats - Pillbox

Another one for the ladies, this pillbox hat is great for anyone looking for a subtle look that will still covey an old-fashioned look.

This sits on top of the head and will look especially good for any woman who has a short or bobbed haircut.

You can make the pillbox work with a long flowing ball gown or something much more stripped back.

There are some people who can even make this sort of hat work with more modern clothing like jeans and a T-shirt.

10. Ascot Cap

Vintage Hats - Ascot Cap

Finally, we have a cap that can work on both men and women. This is another no-frills sort of hat, coming with a short brim that sits close to the head. You can get this one in plain colors or with a pattern.

This is another one that would suit that belt-and-braces look. If you are a fan of the show Peaky Blinders, then this cap will undoubtedly be familiar to you.

If you want to cultivate that lovable rogue look, then this is a great cap to tie your outfit together.

Frequently Asked Questions

Why Should I Wear A Vintage Hat?

If you enjoy wearing vintage clothing, then it will be hard to find a hat that matches.

Vintage clothing can be grouped into certain eras, and only hats from a certain era will match the era of clothing you are wearing (there are a few exceptions that can be mixed and matched).

How Much Will A Vintage Hat Cost Me?

There are hats that are made in a vintage style but are mass manufactured and are not actually vintage hats, more vintage-style hats.

These are usually cheap and widely available in most clothing outlets.

However, if you are going for a genuine vintage hat, then you’ll be dealing with much more expensive materials and designs, meaning that you’ll have to pay a lot more money.

You can probably expect to spend nearly $100 for a decent vintage hat.

What Vintage Hat Should I Get For The Summer?

There are plenty of hats that you can wear during the summer, most of which are cream in color and are made from breathable materials such as straw and wicker.

These hats are also less expensive than ones made from thicker materials.

What Hat Should I Wear With My Ball Gown?

There are a few different types of hats that you can wear with a ball gown. It all depends on the cut of the dress as well as the material.

If you have a dress that is flowery, then you might want to match it with a floppy-brimmed hat.


We hope that our guide to vintage hats has given you some inspo for getting the perfect one for your outfit. If you want to go proper vintage, then you might have to do a little bit of hunting on second-hand websites.

Willa Price