Round Face
If you have a lovely round face with a wide forehead and full cheeks with a rounded chin, then you would ideally need to look for a more angular style hat to balance your roundness. You are lucky that you are able to wear asymmetrical shapes with a high crown and peaked or slanted brim. You can accentuate by slanting your hat forward to create attractive angles. Create length to your face by wearing high crowns which will not only give height but will also slim the face. Straight brims add asymmetry. Choose hats with crowns that are at least as wide as your face. The best hats would be: Bakerboy Caps and Medium-Long Brim Fedoras. Hats to avoid would be: Rounded crowns, wide crowns or brims (as they accentuate the roundness). Instead go for height with a pinched crown and avoid low or flat hats.
Oval Face
If you have an oval (egg shaped) face, you are lucky that you have a versatile choice of hats. Your forehead is slightly larger than your jawline. Your face is longer than it is wide and you have a straight line from your slightly wider temple to your narrower jaw with an angled round chin. Ideally, you would want a hat that sits low on your forehead with a wide or flared brim. Hat styles that suit you best are Fedora Hats, Cowboy Hats, Bucket Hats that sit low on the forehead, Newsboy Caps, Fishermen Caps, Boater style with rounded brims. It's best to avoid narrow or flat brims and go for low crowns and wide flared brims.
Oblong Face
Similar to the oval face, again this is a very versatile shape for hats. You have a high forehead and a round chin. Your face has more length than width. The sides of your face go straight down so looking for round shaped hats to counterbalance these straight lines would usually be recommended. Even out the length of your face with low short crowns and flared brims for width and roundness. Sun Hats with low crowns and wide brims are the perfect style as they reduce the length and the roundness of a wide brim, especially if it's a floppy brim. Cloche Hats worn low to the eyebrows helps conceal high foreheads and can create the illusion of a shortened face. Newsboy Caps and Bucket Hats also suit oblong faces with a low crown and wider rounded brim. Ideally, avoid tall crowns which can over-emphasise the length of your face.
Square Face
If you have a square face, you have a lovely angular shape and a strong jawline. You will have a wide forehead and wide cheekbones. The length of your face will be almost equal to the width. As you have an angular face, go for the opposite to soften the angles by going for curves and round hats to provide contrast to your angular jawline. Floppy hats are a good choice as they have a curvy wide brim to counterbalance the angular features. Curvy lines like bowler hats also suit square faces. Round crowns and brims can smooth the angles of a square face by giving height and roundness. Tilting the hat to the side can help break the symmetry and add roundness to your features. Hats to go for would be: Bowler Hats, Pork Pie Hats, Sun Hats, Floppy Hats, Cowboy Hats, Homburg Hats, Cloche Hats. Look for hats which elongate and cushion your facial contours. Hats to avoid would be short brim or no brimmed hats and square hats – go for rounder hats!
Diamond Face
Like a gorgeous diamond, the forehead and chin are narrower and the cheekbones wider. Again, this face shape has angular contours with a tapered chin. Features to go for would be moderate to wide brims and pinched crowns. Again round style hats can counterbalance the angular contours. Round Bowler Hats can give the illusion of a rounder forehead and Trilby Hats have shorter brims with pinched crowns. Moderate brims help reduce the width of the cheekbones whereas wider brims would emphasise the cheekbones more.
Heart Shaped Face
The lovely heart shape face features a broad forehead and wide cheekbones with a pointed chin – the chin being the narrowest part. Choose styles which slim the forehead to make it appear narrower. Balance out the width of your forehead with a medium brim. By slanting the hat to one side, you can slim your face and draw attention to your eyes. Best hats to go for would be medium brim Fedoras, Boaters, Cloche Hats, Homburgs, Beanies and Berets (as they balance out the width of your forehead). Avoid large brims that accentuate your wide forehead.
Triangular/Pear Shaped Face
The versatile triangular shaped face is like the shape of a pear with it's larger jawline and small forehead and small cheekbones. So just like the oval face, there are endless options with this lucky face shape – you can get away with wearing lots of different shapes and styles! Really all you need to do is avoid crowns that are narrower than your cheekbones – which is actually the case with all face shapes. You can bring balance to your shoulder line and have a taller crown to counterbalance your smaller forehead.