Cover Collection: High-Fashion Hats for the Kentucky Derby

Long before most of us were old enough to know what a horse was (let alone a mint julep), Post ladies were dazzling us with their chapeaus.

A woman wearing a huge hat.
Woman in Huge Hat
by Alonzo Kimball
February 8, 1908

This pretty lady was quite a standout in 1908, with a hat large enough to serve as shade for three. This one must have required several hatpins to secure.


Woman in Plumed Hat, Chin in Hand
by Harrison Fisher
January 18, 1908

Harrison Fisher was an artist who graced many Post covers with lovely ladies. This hat requires a profile view for best effect. One wonders what poor bird(s) suffered for this work of art. Well, they say beauty has its price.


Woman in Paisley Turban
by Harrison Fisher

There are dozens of Post “hat ladies” to choose form, but we couldn’t resist this gorgeous paisley turban. This was also painted by artist Harrison Fisher. We love the color reproduction for 1910.


Women and Dog in Auto
by Harrison Fisher
November 25, 1911

Let’s hope that fancy motor car doesn’t get up too much speed! Somewhere between glamorous and…well, crazy, these hats make a fashion statement…of some kind. Luckily there was still room in the car for the dog.


Coffee and Conversation
by Harrison Fisher
January 20, 1912

Artist Harrison Fisher must have done some serious hat shopping. In “Coffee and Conversation” from 1912, this lady’s headgear is bound to turn some heads. We kind of see Lady Gaga going for this one.


Lady in Wide Brim Hat Holding Tea Cup
by Penrhyn Stanlaws
March 24, 1928

Thank goodness for Derby Ladies! Where else can we drool over these beautiful hats these days? Such as this simply elegant cover from 1928.


A woman looks at horses through a pair of binoculars
Seeing Horses in Binoculars
by Alfred Panepinto
August 21, 1937

It’s Derby Day! Make sure to bring your binoculars so you can watch your favorite pony round the track.

Descriptions courtesy of Diana Denny.