…a dapper and distinguished look


Rich in folklore it’s said that wearing a hat brings one good luck. So what better place than to wear a hat then on Derby day.



Lost among all the color, pageantry, ribbons, bows and styles that make up ladies hats, the art of men wearing hats on Oaks and Derby Day has grown steadily grown.

Yet not traditionally worn year-round just what is the perfect headwear to top off the perfect suit.  Generally it’s a fedora or bowler hat and generally solid in color and inspired by the style from the 1920s.

Choosing the best hat comes from the symmetry of the face. All hats make a man look more dapper, but picking the hat that is right for your face shape always gives you a sharper appearance.



The make-up is simply three parts: crown, band and brim. Hat’s taper and this is how narrow the top of the crown is compared to the bottom. Thus your hat selection needs to compliment the shape of your face.


Short full face – A round face tends to look short, so you want a hat that will give you a little height. Pick a medium height crown with a slight taper and narrow band and moderate wide brim. Tilt the hat back from your face to gain height perception.

You might pick – Fedora, Gambler, or Panama.




Long thin face – You need to find a hat that shorten your face so stay away from crown that are too high or full looking. Select a moderate taper and has a wide band to shorten the fast and a contrasting color with a wide brim. Wear it with a slight tilt to the side and back.

You might pick – Fedora, Homberg or Derby.


Top Heavy face – Find a hat that will help balance your face with a medium or short crown and avoid one that is too high or full looking.

Derby Bowler

Derby Bowler

Try to find a medium to narrow band and brim width and one that rolls on the side and back. You have a wide forehead so don’t tilt it too far back.

You might pick – Fedora or Homberg.


Square face – Your hat needs to add some curvature to your face so a medium, full and round crown is better and no taper. A wide brim will help as well and tilt it just slightly backward.

You might pick – Bowler or Homberg




A prominent jaw – You have a strong and distinguished chin so you need balance with a slight taper and medium crown. A medium brim with no tilt and a minimal tilt will keep the focus off your jaw.

You might pick – Fedora.


So what color do you look for – that depends on the suit.

Brown Hat Brown hats look best with brown or green suits or coats.

Gray Hat Gray hats are quite versatile and can be paired with black, blue, and dark gray suits and coats.

Blue Hat Wear a blue hat with a blue or gray suit or coat.

Green Hat Green hats are surprisingly versatile. They look best with tan or light brown suits. But they also accent black, green, and gray suits very nicely.


Now all you have to do find the right fit. Simply measure your head with a tape measure snuggly just above your ears where that hat sits when you wear it.


Inches 21 1/4 21 5/8 22 1/2 23 1/4 24 24 7/8
USA Hat Sizes 6 3/4 6 7/8 7 1/8 7 3/8 7 5/8 7 7/8