Winters Past

20th Century Fashion from Deco to Disco

Tip Your Hat

I watch lots of people try on vintage hats. Here is something I’ve learned: if you take a few minutes to find the right tilt, you will be much more satisfied with how it looks and feels on your head.

Frank Sinatra said it best: “Cock your hat – angles are attitudes”.

Frank Sinatra hat

Frank Sinatra crooning in a hat

Take a tip from Frank-play around and experiment with how you wear each hat.

First, look at the tag placement-this is always the back.

Then angle it forward, backward and to each side.

Keep in mind that hats these days tend to be worn lower on the head, whereas you’ll notice in vintage photos that hats were often placed on the head and not pulled down. Give this a try.

wear a vintage hat

Thirties ladies tipped their hats

Smaller hats and fascinators were made to be worn more on the side of the head.

If you’re wearing your hat high or far to one side, consider using a hat pin.

Berets shouldn’t be too neat or symmetrical; they look best worn slouched to one side or to the back. It creates a look that is relaxed but still stylish and polished.

Here are some photos of modern ladies in vintage hats:

Author: Winters Past

I am a vintage clothing shop owner living and working in rural north Florida. I believe in adding a little vinegar and molasses to my greens, having my coffee outside whenever possible, and mixing something vintage into every room and every outfit.

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