Gone are the days of the elegant hat for everyday wear: the velvet cloche, the feathered chapeau, the ribboned bonnet, the “fascinator.” (Look it up.)  Unless you’re dressing for the Ascot races, you’ve no doubt noticed that the minimalist direction of fashion has invaded the millinery world. But this doesn’t mean that a hat can’t be part of a fashionable look. In fact, it is a signature for certain style archetypes and often is the anchoring piece for a whole outfit. So how does one determine the best hat to wear?

Well, a lot of the same things we look for in clothing also determine the most flattering style of hat for us:  personal style, height, bone structure. Generally, hats are pretty costume-y. That means that Dramatic and High Spirited Types who can do “costumes” can get away with a lot more hat varieties than other style archetypes, such as Classics, who wouldn’t be caught dead in a costume, and Romantics, who usually like to show off their hair (unless they’re wearing a floppy brimmed style that seductively covers one eye.)

Speaking of which, hair is often the reason we reject any number of styles that might otherwise look great. This is particularly true for those of us with curly hair (and the reason I rarely wear them.) The reality is that most hats look best on flat hair or curly/wavy hair that is partially pulled back slightly away from the face.

Who can Wear What Hat?

Some stylists say that oval-shaped faces can wear any hat. I believe it depends upon your features, size and personal style. You don’t want to put a large, floppy, wide-brimmed hat on a small person.  All you will see is the hat. The taller you are, the more you can get away with a wider brim.

Personally, I think there aren’t a lot of don’ts for who can wear what hat. What matters more is the size and shape of the brim and crown (if there is one) and where the hat is worn on the head. The only exception is for a very long, oval-shaped face which looks more balanced with a medium-wide straight or floppy brim and a fitted crown or an angled beret. Most head/face shapes can wear some form of beanie or beret. A square or round face can handle one with a little more texture and volume. A round face can wear  better something more close-fitting. Someone with a heart shaped, diamond, or oval face can wear fitted cap or one with additional fabric and texture.

Newsboy caps require a broader face, particularly if the cap is flat on top, as with Drew Barrymore’s here. Longer, thinner faces look squashed in a flat cap, unless the crown is a fuller like this one on Kate Middleton.

The Fedora and the Panama hat have had quite a revival the past few years in fashion.The sharp brim of Reece Witherspoon’s short-brimmed Panama here gives a nice counterpoint to her pointed chin and her heart-shaped face. Then there are three women wearing essentially the same Fedora, all with different styles and faces. Jennifer Jennifer Aniston’s would work, but the brim is competing with the top of her glasses. The shorter brim and higher crown on Cameron Diaz’ balances her broad face. And Ann Hathaway’s more Dramatic style caries off a higher crown and tilted brim.

Bowlers are pretty tricky for anyone who isn’t little and doesn’t have a lot of the High Spirited style qualities. Taylor Swift rarely does anything wrong sartorially but imho this little one is a tad small for her head.

Cowboy hats usually require a broader head; the turned up sides will  elongate a face. Anne Hathaway’s rock festival-like floppy straw version is a good compromise for someone who wants the style but not the harder silhouette. And speaking of straw – just about anyone can wear a straw hat, even though it is an element of the Youthful archetype (the fact that the weave is essentially open and loose reads as Youthful.) Almost every type of hat, from floppy sun hats, to fedoras, cloches, bowlers, etc, are available in straw.

And almost everyone has at least one baseball cap in their closet. (Well, maybe not the Queen…) Pay attention to the shape and the width of the brim. A curved brim is more flattering on almost any face than a flat one, particularly for someone with a longer or narrow face. If you have any kind of a poufy hairdo it might stick out from the sides, making you look a little bozo-like.Pull your hair back a bit.

If you’re game, send me a photo of your favorite hat. I’d love to see how you wear it! And to learn more about your personal style archetypes, chapter 3 of my book has a detailed questionnaire that  can help you determine that.

Hat’s off to the Real You!

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