Dilemma solved…Get a new hat that goes with your vintage outfit.

I have the problem. She has the problem. And even some he’s have the problem. I love vintage hats and see so many in the stores that I would love to wear, but I run into the same problem as vintage dresses. They are usually too small for my head.

And now it is Fall, perfect hat weather. So I scoured around for cute new hats to go with my vintage that might actually fit over my overgrown noggin.

Leopard Cap

This pillbox leopard hat from Etsy is so chic. It is an attention getter for sure.

Hats with Bows

This first hat from JJ’s House is in a perfect Fall color and is petite enough to wear with just about any hairstyle.

Here’s another hat from JJs House. It has more coverage than the first one and no netting, but it is in my favorite color of black, black, and more black. It also comes in other fall colors like burgundy and navy.

Cloche Hat

This Wool Cloche hat from Etsy is definitely a full coverage hat.

Androgynous Hat Style

I’m really into this fedora on Etsy that is so Annie Hall. I love androgynous 1930s and 1940s looks.


This beret hat from Lana Blu Designs on Etsy comes in a bunch of colors and looks more vintage to me than a lot of the other berets being sold right now. I love the many different ways you can wear berets vintage style. They have a bunch of other designs as well worth checking out.

Knit Hats

Everyone who reads this blog, knows I love turbans. This turban beanie on Etsy is simple and would be great with jeans and a sweater.

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  1. I WANT everyone one of those hats. Maybe not the turbans. I have the opposite problem, I have such a small head, turbans make me look like a pinhead. But all the others. YES! So cute!

    Thanks for the hook-up with so many hat sites!

    That reminds me, I don’t put my fictional characters in enough hats. Must remember to add hats to the next story. Woo hoo! Thanks!


    1. So thrilled to see this article! I am a Massachusetts milliner starting my own business, hoping to make vintage style hats (as well as repairing originals). This article showed me there is really a need and what sort of hats people might be looking for. Cannot thank you enough for some inspiration! – Sarah

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Welcome to the Bobby Pin Blog! I am Lauren Rennells and as a hairstylist, makeup artist, writer, and generally artistic over-achiever, the Bobby Pin Blog is my outlet for thoughts and research about vintage hair and makeup trends and how to recreate them today. Thank you for stopping by!

As an Etsy and Amazon associate I earn from qualifying purchases. As an independent blogger, I link these items because of my own opinions and not because of the commission I may receive.



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