A great hat is a functional and potentially very stylish summer accessory to have, but is likely to be one of those things you may not quite get round to updating or you choose the first one you find that's practical, without a thought as to whether or not it suits you.
Obviously the most important aspect is for it to suit your face shape, but other things to take into consideration are your overall proportions and your colouring. Keep the hat in proportion to your size (ie: no tiny brims on a very large man or very big hats on a small guy) and in keeping with your colouring eg: if you have warm tones in your skin and hair look for sandy colours, browns and khakis. If your skin is more pinky or blue toned then look for stone, navy and pale blues.
To help give a starting point to your search, here's my guide to choosing a hat to suit your face shape.
In order to elongate a round face shape you need to choose hats with a taller, dented crown and a more angular shape. Choose a medium sized brim which is wide enough to be in proportion with your face but narrow enough not to create more width rather than height.
Look for a skinny or toning hatband if possible, which will give the illusion of extra height to the hat and therefore your face.
A linen or cotton flat cap is a more casual alternative. Ensure the one you choose has flat sides rather than an eight piece style, and wear it slightly back so some of your forehead is still visible and you don't "squash" your face.
"Maverick" straw Trilby hat - French Connection
"Classic" Panama hat - Lock & Co
Herringbone linen flat cap - Borsalino at Mr Porter
A square face shape also needs to be elongated a little and softened with curves and rounded edges which helps to offset the angularity of your face.
Look for hats made of softer, pliable fabric to flatter your face and choose taller styles rather than very wide and flat. A medium sized brim with a curve to it will help and if you wear it tilted at a slight angle it will further soften the square-ness of your face.
Although it doesn't have much height to it, a baker boy or eight piece cap will slice off the corners of a square face with it's curved peak and frame your face well.
Linen and seersucker cotton eight piece cap - Lock & Co
Dip dye braid hat - Paul Smith at Coggles
Superfino folder Panama hat - Christys'
If your face is a rectangular shape it will need to be visually shortened a little. Look for hats with wide brims, and shallower crowns. A deep, contrasting band will help to break up the height of the hat.
For a casual look, a bucket hat will suit your face shape with it's downturned brim giving the illusion of a shorter face, or you could also wear an eight piece baker boy cap in linen or cotton who's width will suit and curves will soften.
Reversible cotton bucket hat - Lock & Co at Mr Porter
Wide brim Panama hat - Lock & Co
Eight piece Baker boy linen cap - Christys'
The heart shaped face needs a hat with a small to medium brim in order not to widen the forehead area any further. Opt for a style with an obviously dented crown and sides which will bring the eye in rather than adding more width. The darker shade of the brim on the hat below will have the flattering effect of minimising the width of the forehead. Avoid hats with flat wide crowns.
Carnaby snap brim bleached hat - Christys'
Beige linen Seville hat - Lock & Co
Crochet raffia Truro trilby - Christys'
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