Winter Is Coming, What Hat Is Going To Flatter Your Face?

My personal style changes more than it should. Every week I have an obsession with something different; whether it be bracelets, earrings, rings, scarves, or literally anything else you can think to put on your body that provides some self-expression. This week it is all about hats!

I only own a few hats mostly because my permanent obsession is high heels. However, this week I found an extremely chic hat at, you will never guess: Wal-Mart!

I have 3 hats total: a black wool fedora, a black wool beret (bought in Paris, so it is authentic), and yesterday I bought a black wool cloche hat. (see picture below)

Wool Cloche Hat

Those are the only three hats that I own currently however my hat collection with be expanding drastically because I was able to find out what best flatters my face. Luckily I am able to pull off a multitude of different hats. Unfortunately, some people look good in any hat they put on, and some people were just not made to wear hats…but it all has to do with your face shape, head shape and the proportions of your facial features.

Small Faces:

If you have a smaller face you are going to need something proportional to your face. Do not go for large hats or hats with a large brim (like beach hats). You are able to wear beanies; beanies sit snug on your head allowing your face to not look like it is being attacked by a wooly animal. My suggestion for hats are either beanies or a small pillbox hat. I have been obsessed with pillbox hats for about a month now…pillbox hats come in a range of sizes so try to find a small/medium size pillbox hat. Kate Middleton and Victoria Beckham can rock pillbox hats because they have petite facial features.

Victoria Beckham – Pillbox Hat

Long Faces: Long faces like Sarah Jessica Parker or Kate Beckinsdale require a little coverage of the forehead. Look for a floppy hats with a medium flared brim or a cloche. Avoid narrow brim hats because they will only elongate your face.

Flaired Brim Floppy Hat

Round Faces: If you are anything like me, you have a round face. What people need to remember when wearing hats with a round face, make sure the crown of your hat is no wider than your cheek bones. When the crown is wider than your cheek bones it will make your face look wider than it actually is. Look for hats with asymmetrical lines and angles. Look for conductor hats or a fedora. Disclaimer: I have a rounder face, however I wear a cloche hat and I can pull it off. If you have a face that is in the in between the definitions of the face shapes in this blog, then try a multitude of hats, you may be pleasantly surprised to find what might flatter you!

Conductor Hat

Square Faces: Think Angelina Jolie or Sandra Bullock.  So what you are looking for is opposite of your face shape, meaning a larger brim and a rounded crown, like a great big beach hat! The roundness of the crown will help reduce the harshness of points on your face. Don’t be afraid to tilt your hat to give the hat more definition. Look for bowler hats or a large floppy hat.

Bowler Hat

Heart Shape Faces: Jennifer Love Hewitt and Reese Whitherspoon have heart shaped faces. Do not get a hat with a narrow brim, this will only accentuate your forehead making it look bigger and wider. Look for a medium brim hat, if you go for a wide brim hat it will make your already pointed chin look even pointer. You also are able to wear a cloche, however make sure the brim is not too narrow and not too large!

Cloche Hat


I usually say the best thing a woman can wear is her confidence. I you find a hat that you think flatters your unique face shape, that you feel confident in, rock it until the wheels fall off. If you have more confidence in a hat that is contrary to what this blog says, you go! Confidence is a womans best asset and if you can exude confidence, all the more power to you!




About Rachel

My name is Rachel Boudreau. I am 24 years old and have been blogging for the Bangor Daily News for almost a year. I am a Certified Personal Shopper and a Certified Fashion Stylist. I have always had a complete love and desire for anything fashion. I have recently started studying French fashion, (Dior, Chanel, Louis Vuitton, etc.) I watch all of the high fashion runway shows every spring and fall. I love shopping for people and picking out clothes for them because I like when people try things they normally would not, that, after all, is how you find new things you like! Happy reading!!!