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

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 with 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

If you feel a little too sassy in a full leopard print outfit, this pillbox leopard hat from Etsy is so chic. It is an attention getter for sure.

Disclosure: Bear in mind that some of the links in this post are affiliate links and if you go through them to make a purchase I may earn a commission.

Hats with Bows

This first hat with the cute bow at the back is in a perfect Fall color and is in a size to wear with just about any hairstyle.

Here’s another hat with a cute bow, but in front. It has more coverage than the first one, but it is in my favorite color of black, black, and more black. It also comes in other fall colors like burgundy, camel, and navy.

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Cloche Hat

Cloche hats are often bell shaped and are designed to fit close around a classic bob hairstyle or finger waves. This Wool Cloche hat from Etsy is such a cute option and comes in other colors.

Androgynous Hat Style

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

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Classic Beret

This beret hat from ReneDream 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.