Get a head start on the season’s most stylish hats!
How to find the ideal hat to frame the shape of your face perfectly.
6 July, 2020 by
Get a head start on the season’s
most stylish hats!
Vooma - HealthyLifeCycle

Ah, the elusive but strangely alluring world of hats: most of us think that they are either for royal weddings and other gala occasions (when our invitations don’t get lost in the post) or to cover up  bad hair days – which is actually quite ironic, as hats are often the cause of bad hair days!

Have you ever gazed longingly at photos of hat-clad celebrities,  firmly believed you could carry a fedora off with the same elegance and panache as, say, Beyoncé or Cameron Diaz, rushed off to the store and bought one, designed a whole outfit around it and  boldly sallied forth into the public eye?

I have; first, my teenage son mowed me down with an air machine gun as I walked to my car, while calling me “Al” in his best Mafioso accent. Naturally, I ignored the style Philistine I had bred, though my confidence was slightly dented. “Never mind”, I thought to myself, my lovely bunch of ladies who lunch will admire my flair for headwear and applaud my daring fashion foray.

Fat chance. Sweet, polite Rozanne looked at me and said “Ooh look. You’re wearing a hat.” Non-committal but damning nonetheless; Debbie asked if I had run out of dry shampoo, and Cheryl rolled her eyes wryly and observed that she hadn’t gotten the email about fancy dress.

Chastened, I took it off and tried to ‘bouff’ out my bangs, while kind-hearted Jilly worked on fluffing up the flat bits at the back. Tish, who had remained silent, then proclaimed “Good, now we can eat at last”, as if my fedora had been a huge obstacle to giving our orders to the smirking millennial waiter (waitron? waitperson?).  My BFFs clearly thought I would be better off eating my hat than wearing it on my head!

We have never mentioned my fedora fashion fail again, and it now lives quietly in the back of my closet, minding its own business and keeping out of trouble. Sadly though, my hankering for hats is still as strong as ever, but now I’ve done my research and discovered that there is no such thing as ‘one style suits all’ when it comes to choosing a hat that will turn heads in a good way – and without further ado, I am going to share with you the secret of success: it’s all in the shape of your face!

Basically, face shapes can be divided into 5 different categories:  OVAL, ROUND, OBLONG (or LONG), SQUARE and HEART-shaped:

However, before you think defining your face shape is going to be easy, I have to tell you that even here, it can get complicated, and various beauty pundits even extend these basic categories to include DIAMOND (a sort of angular OVAL) and TRIANGLE (a sharper, more defined HEART).

BUT WAIT, THERE’S MORE: it seems that your face can be a combination of two shapes!
To explain, I will cite some celebrities here, to give you a visual reference: Angelina Jolie is apparently a LONG SQUARE (would that be a RECTANGLE?),  Zooey Deschanel is a ROUND HEART and Sandra Oh a LONG HEART; Rihanna is considered by some to be a SQUARE, and by others to be an OVAL, while Cameron Diaz is deemed to be ROUND when plumper of face, and SQUARE when at her slimmest. Weight fluctuations also affect Beyoncé, who moves between ROUND and OVAL.

No matter: for the benefit of my not-so-famous readers whose face shapes are not going to inspire column inches on the accuracy of the categorization, I will stick to the BIG FIVE, and talk about the hat styles that work best with these…

OVAL                                                                                                                                         This face shape results from the forehead, cheekbones, chin and face height being well-balanced and softly contoured. 

It is the most classically proportioned, and thought to be the ideal hat face, suiting nearly every style of headwear out there – from baseball caps to Stetsons, berets, cloches and wide-brimmed sunhats, the choice really is all yours!

Lucky OVALS share their shape with Kate Middleton (Duchess of Cambridge), Tina Fey, Jamie Lee Curtis, Selma Hayek, Jessica Alba and Oprah Winfrey.

ROUND                                                                                                                                     Here, your low, flat cheekbones are the widest part of your face, which is shorter than it is wide, and gently contoured, with a small, curved jawbone.

High crowns and straight brims can have a slimming effect on round faces, while asymmetric angles add definition and interest. Fedoras and trilbys are good choices (especially when slanted forward), along with baseball and newsboy caps.

Mila Kunis, Queen Latifah, Katy Couric, Drew Barrymore and (surprisingly, I thought) Penelope Cruz all move in the ROUND circle.

OBLONG/LONG                                                                                                                   From hairline to chin, your face, is longer than the widest part of your cheekbones or jawline, and your forehead is higher than most.

Try sunhats or fedoras with low crowns and wide, flared brims to detract from the length of your face. A cloche or beret, worn low on the forehead, close to your eyebrows, can also go a long way to creating the effect of a shorter, even fuller face.

LONG faced ladies include Iman, Courtney Cox, Liv Tyler, Gisele Bundchen and the ageless Meryl Streep.


Your facial bone structure is broad, with your forehead, angular cheekbones and strong, straight jawline all being the same width.

Avoid hats with square crowns, short brims or no brims, they just accentuate your angles; a homburg, cowboy or sunhat, worn at a jaunty angle, will break your facial symmetry.  A cloche or a toque can also look soft and feminine.

Emily Deschanel has SQUARE ‘bones’, along with Keira Knightley, Sandra Bullock, Jennifer Aniston, Katie Holmes, Demi Moore  and Lucy Liu. HEART
The widest part of your face is your forehead, then your cheeks, which taper down to a pointy chin. 
You can really wear any hat without a wide brim, which would only exaggerate your forehead and make your chin look narrower.  A fedora or homburg with a medium or short brim look great worn at an angle, and beanies, berets, caps, cloches and pillbox hats work well too. 

If you have a HEART, you are in good shape, along with Halle Berry, Eva Longoria-Parker, Nicole Ritchie, Scarlett Johansson and Reese Witherspoon. 

I hope this blog helps all you hat-lovers in the Vooma community to work out your own  face shape and choose the hat that suits you best.

Me?  Right now, I’m looking for a wide-brimmed beret with a pointed crown and possibly earflaps, because according to my somewhat dubious calculations, my face shape is a LONG, ROUND SQUARE with HEART shaped accents and an OVAL punchline! 

Wish me luck, I know my hat is out there somewhere.