Find Out How to Wear a Hat the Vintage Way

Evelyn Wood
by Evelyn Wood
5 Materials
10 Minutes

Retro styling is awesome. Really, it’s great, but some things leave us feeling a little gobsmacked on how they can actually be styled. One such accessory in question is how to keep a hat on your head. As we know, vintage hats come in all sorts of crazy shapes and sizes and are not ideal in a practical way. Luckily, I have all the tips and tricks for you on how to wear a hat. Keep on scrolling to see how you can achieve this somewhat daunting task in 4 different ways.

Tools and materials:

  • Assorted hats
  • Hatpin
  • Elastic
  • Bobby pin
  • Hair comb
How to wear a hat


This is a more traditional way that has been used throughout the decades. You can find these in vintage and antique stores. This pin is my favorite! Place your hat on your head, and slowly push through the hatpin so that it slightly scrapes your scalp. Pick up a little bit of hair and push the pin back through on the other side. 

Keep a hat on your head

This hatpin works like magic! If it’s also a windy day, you can add two pins for a better grip. 

How to keep a hat on


Hat elastics are mostly used in tilt hat styles, especially those that were worn in the 1930s. This is a safe, easy method that really does the job! 

How to keep a hat on your head

To wear this correctly, simply wear a hat, pull the elastic from the back, and tuck it under your hair. The elastic should sit right on the nape, around the back. The beauty about this is that your hair will simply cover it all. 

Bobby pin

This is a trusted trick for many. Personally, I feel a hatpin is way better, but if you only have bobby pins lying around, then this will also do. To start, you want to use a hat that has a hatband, as shown. So, slide the bobby pins in and place one on each side. 

Now, slide the hat down onto your head and grab your hair as it goes down. It’s a little tricky to get right, so you may need to perfect the technique.

Hair comb

This is a method that I mostly use as it is so discreet and works like a charm. All you do is attach it at the back by hand stitching it down, as shown. Basically, you want the teeth part to glide down your hair. It’s pretty simple to put, and no one will ever notice the difference.


So, there you have it. Four great tricks to wear a hat and keep it on your head without it falling off. Most of these accessories are available and your local stores; however, the hatpin may be a little harder to find. Now you can safely and elegantly wear any hat you like!

Suggested materials:
  • Hat
  • Hatpin
  • Elastic
See all materials

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Join the conversation
3 of 8 comments
  • Audrey Audrey on Mar 07, 2022

    I love hats wish they would come back in style my granny had dozens of pins I knew what they were for when i was very young.

  • Geraldine Geraldine on Mar 13, 2022

    I love e to wear hats but I wear glasses and I just feel it's to much face wear with a hat and glasses what do you think?

    • Earline Berndt Earline Berndt on Mar 15, 2023

      Just find a hat you really like and go for it. I have glasses and wear hats all the time.

      once you get used to them you'll love it.