Which Hat to Buy for Your Face Shape

To determine which hat to buy for your face shape, first you need to decide on the shape of your face!

Look in the mirror head on and draw the outline of your face in the mirror with some lipstick (though maybe not your favourite one). This is messy but necessary. When you move away from the mirror, you can see much more clearly the shape of your face, how much wider it is at the top than at the bottom, how much your chin comes to a point, or how long it is.

  • Is your face widest at the cheekbones, with a shorter, more narrow forehead and jaw? You’re a Diamond.
  • Is your face longer than it is wide, with your forehead, cheekbones and jawline all the same width? You’re an Oblong.
  • Do you have a larger jawline, with smaller cheekbones and forehead? You’re a Triangle.
  • Do you have a wider forehead and cheekbones, but a smaller, tapered chin? You’re a Heart.
  • Is your face longer than it is wide, with a narrow forehead, cheekbones and jawline? You’ve got a Long face.
  • Is your face the same in width and length? You’ve got a Round face.
  • Is your face the same width and length, with a strong jawline, wide forehead and wide cheekbones? You’re a Square.
  • Do you have a face whose length is roughly one and a half times greater than the width, with a forehead that is slightly larger than the jawline? You’ve got an Oval face.

So now that we’ve clarified your shape, follow this guide to see which hat you should buy for your face shape.

See also our tips for How to find your Ideal Hat

Main picture, left to right: Beata, straw summer beret, £230 and The Aage Summer Races Hat, £280, both by Maggie Mowbray Hats (Etsy); ‘Jo’ Bumper Coolie with collage print and adorned with coloured pearl balls and tulle pompoms, by Harvy Santos, ‘Fizzy Pop’ collection.


Goals: lengthen face, widen forehead.

Approved: a shallow crown worn further back on the head. A medium brim, with some side detailing to widen the forehead. A pill box style would suit you.

Avoid: wearing a hat that sits lower than your hairline, floppy hats or wide brims.

Try: Joanne Edwards’s Ophelia Pill Box with handmade flowers, £465 from Etsy.


Goals: shorten face, add width, soften jawline.

Approved: a short crown – slightly flat – and a wide or flared brim, such as a fedora, worn low over the forehead.

Avoid: tall hats, or hats with narrow or flat brims.

Try: Saucer hat with Ostrich trim, £160 from Ostentatia on Etsy.


Goals: balance your hat with your shoulder line, add width to your forehead.

Approved: hats that sit across the brow/hairline, high crowns. Details at the side of the crown will widen the forehead.

Avoid: crowns narrower than your cheekbones.

Try: Scale by Laura Aspit Livens, ‘Semi-Construct’ SS17 Collection.


Goal: narrow your forehead, don’t overbear your chin.

Approved: hats with a prominent square or round crown, a medium brim which can be slanted. Fedoras and asymmetric hats such as a cloche work well.

Avoid: wide brims, floppy hats, chunky hats: the brim shouldn’t be wider than your cheekbones.

Try: Cierzo by Laura Aspit Livens.


Goal: shorten your face and add width.

Approved: hats with fitted or square crowns and wide hat bands, worn across the forehead to soften. Try a floppy hat with a deep crown.

Avoid: shallow or tall crowns, short brims, and wearing hats behind the hairline.

Try: Deco by Laura Aspit Livens.


Goals: lengthen, add angles, asymmetrical.

Approved: high but not rounded crowns, something the same width as your face. Go for a peaked medium or small brim, like a fedora. Trimmings such as upright feathers will lengthen your face.

Avoid: round or floppy wide brims, inverted ‘flower pot’ shapes.

Try: Reflections, mirror headpiece on a button base, £980 from Ana Bella Millinery.


Goals: soften, lengthen, and add curves to your face.

Approved: circular hats with rounded brims, such as floppy hats, cloche hats or bowlers. Soft, wide brims and rounded crowns are definite choices. Wear it on a slant.

Avoid: angular hats, hats worn too far back, short brim, square crowns.

Try: Pink Evelyn hat with flower, £290 from Ana Bella Millinery.


Goals: fashion forward, large brims.

Approved: anything and everything! This is the most versatile face shape, so you can’t go too wrong. You can get away with large floppy brims.

Avoid: crowns narrower than your cheekbones, brims wider than your shoulders.

Try: The Lilly Halo Crown, £250 from Maggie Mowbray Hats (Etsy).

For further racing fashion tips, plus advice for men, which hat to choose for your face shape, and summer make-up suggestions, see our Summer  Racing Fashion Guide 2017.

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