How to Choose a Hat to Flatter


Winter over here so finding a flattering winter hat is difficult. Would welcome advice for this. Liz


Firstly you need to know what your face shape is – you don’t need to be overly specific, just about the length to width ratio – for more information on figuring out your faceshape which you can do by reading here.

There are two major points of a hat to consider – the crown and the brim.

  • Tall crowns will make you look taller.
  • Wide brims will make you look smaller.
  • Downturned brims will make you look shorter.
  • Upturned brims will make you look taller.
  • Wide brims will protect you from the sun more.
  • Wide brims and shorter crowns suit longer face shapes.
  • Short Faces need taller crowns.
  • Deep crowns – ones that your head fits right into, rather than the hat being perched on top of your head and full of air, suit long faces and should be avoided by short faces who need shallow crowns (the ones that sit up high on your head).
  • Berets work better on shorter faces shapes than longer ones.
  • Peaked crowns (like in a Fedora style) work well on shorter faces shapes as they give the illusion of more length.

Hats should generally be worn on an angle rather than just plopped straight onto your head.   But try them forward, backwards, angled, to see what suits your face shape and hairstyle.

Many hats are made to be worn angled onto the right side of your head – so if you have a part on the left side you may need to swap your part over as the hat should sit on the side with your part so your hair volume balances the hat.

Hair Tips for Wearing Hats

A quick word on hairstyles – generally hats work better if your long hair is tied back, or with it straight and smooth tucked behind your ears.   Too much volume from long hair can overwhelm.

And how to avoid hat hair?  Make sure your hair is completely dry before you put on your hat.  You will get some indentations, so try wearing a style, whether tied back or smoothed down that doesn’t look odd with a flattened top.  After you take off your hat, turn head upside down and run your fingers through your hair to try and get a little volume back into it.

More Tips on Choosing and Wearing Hats

How to Accessorize in Winter

Tips for Finding a Flattering Sun Hat

Spring Racing Carnival Headwear Tips

What to Wear Spring Racing and Melbourne Cup


How to choose a hat to flatter your face and features


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  • Hi Imogen. Delighted you have brought up the tricky subject of hats. Do you have any suggestions for people with small faces? I usually avoid wearing hats, although I love them, because most styles make me look as if I’m using the hat as a tent rather than an article of clothing. Oh, and since I live in Scotland, warm hats that don’t blow off are an essential accessory in the winter. Many thanks, Anni

  • When I was young I would always go to the hat section and try on hats. I still love hats but no one wears them and what was once considered a normal, every-day thing is now rare. So how to feel comfortable wearing a hat you love would be a good post? No?
    I loved Revolutionary Road with Kate Winslet & Leonardo DiCaprio, there are numerous scenes where everyone wears a hat, to go to town, to go visiting, to go to work. One scene has all the men catching the train to work and it is just a sea of grey flannel and hats. I wish that would return.
    I love the fashion of the late 30’s and 40’s

  • I have a heart shape face and to my surprise a wool turban works well. The front is gathered by a loop so its asymetric. Much better than a beanie or bobble hat. Also as I have short hair a headband is quite flattering as well. I got a bit lost with the hat rules. I am 5’4″. Is a top hat my best option:) ?

    • The turban front works as an asymmetric fringe/bangs on you, which is always balancing the wide forehead of a heart-shaped face and that is why it looks so good on you. Also, a turban does not have a brim, so it does not enhance in width that much.
      To me, turbans have always felt more like playing with the hair than adding volume, as a hat does.
      How do you feel about that?

  • I think I’ve got a shortish but small head but I think cloche hats really suit me. I love the art deco period.


  • With a square face ,my brim needs to be “more” than the crown.
    Yes, beret needs to cover the hair part!!
    Good info!!

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