It’s spring, so it seems like the perfect time to consider wearing a hat—whether for Easter or for some other occasion.

1939 French fashion magazine image, offered by


If you have hats and you love them and feel confident and beautiful in them, hooray! If you feel awkward and afraid you aren’t right for hats, keep reading. I say thehat just isn’t right for you .

Most every modern woman, at some point, has considered her face shape when choosing how to wear her hair. I’ll bet you know how your face compares to oval, round, square, diamond and heart shapes and how your hair interacts with that shape.

Women used to know these same things about hats. I have purchased collections of hats from the estates of women I never glimpsed, but I could tell you things about them, maybe even their height, coloring, face shape and style.

There are some basics.

If you are petite, a small hat will highlight your look without overwhelming you. Cloches, as well as the fitted hat styles of the 1930s, 1940s and 1950s may work best. Also consider small pillbox hats from the 1950s and 60s. If you are more statuesque, the opposite can apply. Too small a hat might be lost on you, and you can balance your features with something on a larger scale. There are choices going back to the Edwardian era as well as wide brim cloches from c1930. Look for picture hats and outgoing shapes from the 1940s, 50s and 60s.

This face shape diagram (grabbed from

this Pinterest board

), seems to date from the early 1940s. Look at the way the face shape is enhanced or altered by the hair style and the hat.

That said, there are so many rules that are better off broken. Do you have wide-set eyes? The conventional wisdom would be to deemphasize the width at that point on your face. But if you love to emphasize this interesting feature, then let a line of your hat be at eye level. 

Eyes in general will be a strong focus with a hat veil or a tilted brim. Slightly hidden, any feature is more alluring, but especially the eyes. Does asymmetry or symmetry work best on your face? Hats can emphasize or deemphasize. Your whole face is in focus with a hat. Don’t be afraid, your hair is already doing this, so a hat just gives you even more options.

Consider a hat in a color to complement your own, and your wardrobe’s. 

Shape, size, angle, symmetry, era, color—does this seem like just too much? 

Don’t we paint miniature scenes on our fingernails in 2015? The effort is all a matter of perspective.

What we have going for us in 2015, hat-wise, is free rein. Many are wearing different eras of clothing and accessories with increasing knowledge and sophistication. Sometimes a vintage hat is part of a single-era costume, at other times it adds some playfulness to a modern style. Allow your taste to answer the question,

does this work?

It sometimes helps to get impressions from famous faces with varying hats. Era aside, which hat do you most like on each of these women? Why?

Brigitte Bardot

Ava Gardner

Marilyn Monroe

Audrey Hepburn

Jackie Kennedy

Gene Tierney

I know what you’re thinking...these women are all so beautiful they could wear anything and look sensational. But look at some “regular” women, would any of them look better without her hat? I don’t think so either.

My collage of photobooth shots

Want to try on some fantastic modern hats in all shapes, sizes and colors?

has a try-on feature where you can upload your own photo and see yourself in millinery by the likes of Gina Foster, Noel Stewart and Philip Treacy. Some look very vintage-y, while others are completely avant-garde It’s both a virtual delight and pretty darn educational about what works on you. I loved this one on myself. (Shall I tell you when my birthday is?)

It’s Spring—almost Easter—why not try on a hat?

P.S. If you are sure you can’t find a hat that works well on you, let me know. I will find you one that I believe is YOU.