How to Sell: Hats

This is a super cute hat that is flat and brimless. The material is gathered on the side with a rhinestone.

Just like vintage purses, there are a lot of different styles of hats, especially if you throw in all of the typical fashions from decades past. Today we’re going to mention a few so you can identify them when you’re out and about at auctions, estate sales, and garage sales!

(Because we don’t have pictures of each type of hat, I’m linking the names of them to their respective Wikipedia article. Looking at pictures is the best way to learn the different styles, so make sure you check them out!)


A. Cloche – This is a very 1920s style hat. It is bell shaped and sits tightly on the head, with the front coming down to pretty much cover your forehead. These could be worn plain or highly decorated, and apparently how you decorated your hat said a lot about you!

B. Pillbox – This style of hat reminds me of Jackie O, so it has a serious 1960s vibe to it. The shape is pretty common (and the name fairly self explanatory) – it’s rounded with vertical side, and sits right on top of your head. Check out this search result, and you’ll see that almost every hat that Mrs. Kennedy wore was a pillbox.

Here’s a fancy pillbox hat with a netted top – it’d be perfect for wearing to the theatre!

C. Wide-brim – This link will actually take you to an article about cowboy hats, which are a type of wide-brim hats. These are pretty easy to figure out – it’s any hat that has (wait for it…) a wide brim!

A very cute vintage wide-brim hat. This style is timeless.

D. Fedora – This hat is probably the most iconic one on this list. It’s defined by a medium-sized brim, and the typical “pinched” look of the crown. These should bring up images of 1930s gangsters holding tommy guns in one hand and a cigarette in another.

E. Bowler – Think of the fedora, minus the “pinch” and with a much rounder crown, and you’ll get the bowler hat. These were worn by the working class in Victorian England, though the style did jump the pond to the Americas where it was eventually referred to as the “Derby.” (The nerd in me is saying, “Think of Cornelius Fudge from Harry Potter! He wore a LIME GREEN bowler hat!!)

F. Bonnet – This is a pretty common and distinctive hat. It’s usually made of cloth and is brimless. This was generally used to keep your hair in place and clean. At first they didn’t cover any part of the forehead, but they eventually began transforming and some of the later styles were quite different from the originals.

G. Newsboy – These are pretty similar to the beret, except that they have a brim (much like a baseball cap would) with a button that attaches it to the main body of the hat. These were typical of the late 1800s and into the early 1920s, and weren’t just worn by newspaper boys. In fact, I often associate these with Scottish/Irish working class men, but maybe that’s just because I’ve seen The Molly Maguires one too many times.

This could probably be described as a fashionable beret.

How to buy and sell:

There are many more styles of hats than the ones that I listed above. Even among each distinct style (ie. the cloche, the bonnet, the fedora, etc.) there are differences that almost warrant their own category. These are pretty popular ones though, so if you can master the looks of these, you should be fine when hunting for vintage treasures.

It’s important to keep in mind that not all vintage-style hats are actually vintage. Whenever you can, try to double check with whomever you’re buying it from that it’s not a reproduction piece. If it has real feathers and real fur, that increases the chances that it’s authentic.

This could probably be considered a women’s fedora, or maybe even just a wide-brim hat.

Condition is always super important. Check for missing feathers. Check for stains. Check for tiny holes where moths may have gotten to the material. If you’ve come across an awesome find and it’s a little beaten up, don’t worry about it too much. There are still plenty of people out there who will take the time to repair vintage hats and restore them to wearable condition.

Always try to pinpoint the era – is it 1920s or 1950s? Many people like to shop by decade, so this might even be more important than knowing what type of hat you have. Wikipedia has a great list of the different fashions of various decades. Skim through them to brush up on your information.

Accessories like hat boxes are always great to ship with your hats – they’ll keep them safe and give the buyer something to store them in. Hat boxes also sell really well on their own!

This is an adorable vintage hat box that features ballerinas!

This is a slightly newer hat box.

Lastly, be very upfront about the material. If it’s made of fur or feathers, don’t skirt the obvious. Tell your buyers this information and – if you can – what kind of fur or which bird the feathers came from. Wearing fur today is generally looked down upon, but in the early 20th century, it was a sign of social status. There’s nothing wrong with selling vintage fur – we’ve done it a million times and we’ve never gotten any hate mail for it. (But also be aware of eBay’s policies. You don’t want your listing to get pulled!)

A gorgeous pillbox covered in tiny feathers.

A beautiful hat – maybe a cloche? – made of fur.

What are your favorite styles of hats? I love the cloche for women and the newsboy for men, though the 1950s in general speak to me pretty loudly when it comes to fashion. If you had to pick an era to live in, which would you choose?