Three Summer Hats


Following on from the introductory article on the summer hat, I thought it only sensible to explore the topic a little further with some discussion on the summer hats themselves. This is by no means an exhaustive review. There are so many types of light summer hat available in classic and contemporary styles and colours and the examples of hat examined below will not appeal to everyone; however they are distinct enough to merit individual discussion.

The Straw Boater

First up for examination is the straw boater. The Henley classic, the boater is a style of hat rarely seen. It has a flat top and a flat brim and is made from a thick straw. To some it looks a little dated; the heyday for this youthful creation was the early half of the 20th century and since then it has been relegated to ‘ceremonial’ wear at regattas, Harrow School and by barbershop singers. It would take a brave and rather dandy-ish chap to adopt the boater for non-ceremonious occasions. Perhaps a man who favours the elegant clothing of the high-collared Edwardians would consider this a serious piece of headgear; it is a little out of sync with modern fashions.

Having said that it is a very natty design and a proper boater will have a large enough brim to keep you cool on rather too sunny a day. And if you are off to the polo, or the racetrack, the tennis championships or even a wedding, a boater is an excellent item to wear. The best way to wear it is a little jauntily in the spirit of Maurice Chevalier; a little smile and a good deal of bonhomie are the best accessories.

The Pork Pie

The ‘porky’ has experienced something of a renaissance recently. It was one of the designs that seemed to match so very well the avant garde collections of Dior Homme. It was famously worn by jazz musicians of the 1950s and ever since it has had those connotations. Jude Law wore one as jazz-loving Dickie Greenleaf in The Talented Mr Ripley and Pete Doherty, though not exactly a jazz fiend himself has often worn one in the same cocksure manner. Though some wear the pork pie hat like a boater, and others flat across the head, one of the most charming methods is to push the hat back on the head like an errant schoolboy, exposing your forehead and some locks of hair. This does, however, have the disadvantage of exposing your face to the sun.

The Summer ‘Bogart’

The summer ‘Bogart’ is rather a generalist term for any hat that happens to look rather Bogart-esque; like the summer version of something from one of his classic gumshoe films. Panamas would count in this category, particularly the Monte Cristi wide brims, Savannahs and Trilbies. This is the grandest and particularly the most user-friendly of the summer hats available to gentlemen. The Trilby is a little less grand than the wide brim, which in certain tones like berry red and black almost looks like an elegant cavalier chapeau; sans feather of course. The ‘folders’ – panamas that fold up, suitable for travel – are certainly practical but their conservative shape would probably appeal more to older men. The Savannah has a flatter brim and though created as a hat for gentlemen has good popularity among women but the timeless colonial design still looks marvellous on gentlemen of all ages. This style of hat is appropriate with anything from casual cardigans and shorts to three-piece linen suits. I wear a wide brim slightly cocked to the side for a little brushstroke of ‘character.’


Winston Chesterfield is an amateur composer, fashion blogger, trained lawyer and style aficionado. He lives in Westminster, London and blogs at


  1. Hahaha such a unique hat! Guys must look really cool with this kind of hat 😀