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Hat collage copySome people look good in anything. Really anything. The rest of us have some remarkable feature––our best, our worst or the average of both––that becomes a force to be reckoned with, especially when we’re choosing a hat. In any case, we can’t just plop any old hat on our heads and hope for the best.

I’ve been going though my hat wardrobe, looking for one to wear to a very special event. What a riot that has been. After a lifetime of collecting hats, it reminded me of the Kurt Vonnegut short story, “Who Am I This Time?” Or rather, “What was I thinking?”

For best results, choosing a hat is like picking a bra: it should be done with intimate knowledge of your unique situation at a particular moment in time. All I can say for some of the hats in my collection is that I was a different girl when I chose them. Others are still good because they so obviously follow the hat wisdom I found while researching ideas to share with you.

Here are a few good tips to help you choose a hat perfectly suited to you.

Small faces: Choose something proportionate to the size of your face. No large brims or crowns. Of course, the opposite is true for large faces: avoid face-hugging styles.

Long faces: Choose a hat that sets lower on the forehead. Circular brims help widen the face. Avoid crowns that are too high or too shallow, which can accentuate length. (This is my face shape, and I am happy to show you several instances when I failed to apply this principle.)

Round faces: Choose hats with angles. Don’t wear anything too far down on forehead. Hats with round shapes mimic the face and are less complementary. Fedoras: yes!

Square faces: Choose hats with round features and curves. Floppy hats are generally flattering for all, but they are especially good for square faces.

Heart-shaped faces: Avoid hats with wide brims because they accentuate the narrowness of the chin. Short brims are perfect for you.

What to do with your hair? Tuck your hair behind your ears. If your hair is short, a small amount of hair can (and should) frame the face beneath your hat.

What about color?

  • Pale complexions look good in warm colors.
  • Dark skins should avoid dark hats, unless they have bright colors or flowers for contrast.
  • Consider your eye color. Whatever accentuates your eyes in clothing will be dynamite next to your face. Choose trims that accent eye color.
  • Do match lipsticks with hat colors–warm lips with warm colors, cool lips with cool colors.
  • Think about making some contrast with your hair color.

What are you wearing it with?
Hats do not need to match your outfit. In fact, it’s better if they provide contrast. Wear a brilliant green hat with a beige suit, or a purple hat with navy.

What about fit?
A hat shouldn’t squeeze your forehead or fall over your ears.

The final word.
If you aren’t sure whether a hat flatters you, try tilting it to see if the change makes it more interesting and flattering to your face. Rules shouldn’t be hard and fast. If you feel terrific in a hat, consider breaking all the rules!

Finally, if you can’t handle attention, don’t wear a hat. People love hats! They may not feel comfortable in them, but they will admire you for wearing one.

Hat collage 2 copy

In my next post, I’ll share some of the best hat resources on the web. Meanwhile, ask me anything you want about my hats. I’ll not only answer; I’ll enter you in a drawing for A Vintage Novel, a new book recently reviewed by my blogger friend Jody DeFord.

Can you guess which of my hat(s):

  • Helped end an already unhappy roommate relationship?
  • Kept the sun off my face in Italy?
  • Seemed perfect at 30, but unimaginable at 53?
  • Is a direct violation of the hat rules for my long face?
  • I bought in New Orleans?
  • Is too tall? Is too shallow for my face shape?

Life is short. Wear the good stuff.