The art of stylishly covering pates is a delicate one. Less formal hats, those that sit between the topper and the cap, can be troublesome. The trilby and the fedora fit the bill. Both were named after fictional females at he end of the 19th century and swiftly adopted by gentlemen looking for more relaxed style. Edward VIII took to wearing a trilby on the golf course.

“The majority of those who come into the shop have never bought or worn a hat before,” reveals Michael Hagon, Senior Manager of Lock & Co Hatters of St James. “People can be nervous about hats. They know about suits and shoes but hats can be a disconcerting experience.”

Get ahead in the style stakes

Lock & Co was founded in 1676 and is a Royal Warrant holder. “We take great care in ensuring that we never over hat people and find the perfect proportions for the individual. The aim is to feel comfortable with the process but also have fun!” believes Hagon.

Sporting tip top titfers at Aintree

The Wetherby (£365) is the quintessential racing felt, and is hard to best. It is made from top-quality, stiff fur felt and is unlined. The hat features a leather headband and narrow grosgrain band. Although it is available in green or brown, the latter is the big favourite. “About eight of 10 choose brown,” reveals Hagon. The Sandown (£325), as worn by Sean Connery in Dr No, has a narrower brim, while the York (£325) a wider brim but the same racing specifications.

Hats that are odds-on winners

For something that sits easily at the races and in town,  Hagon suggest the Haydock (£225) in green. “It is a fantastically versatile, midweight felt, easily at home in town or city,” he says. “Green is a very understated colour, but in my opinion it goes equally well with brown, camel or tweed.”

And for those who feel that their hat-wearing is ready for the next stage, the Homburg (£345) flits between the traditional and the fashion-conscious with remarkable ease, “although it is quite a lot of hat to wear,” advises Hagon.

A heads-up on what to wear

Christys is another behemoth of the hatting world. The firm was established in 1773 and is famous for its red boxes. It could be described as the ‘Godfather of British hatmaking’ on account of Marlon Brando wearing one of the company’s Homburg hats when he played Don Corleone. Other famous Christys’ wearers include Brad Pitt and Winston Churchill.

The Kent trilby (£190) comes in eight colours, and the silver sits particularly well with a casual look. Anyone wishing to tick traditional boxes, should consider the County (£190), with its drooping brim.

Hats on sale during the Cheltenham Festival

A head start in the comfort stakes

Gamble & Gunn is a British maker based in Devon. It makes hats for both men and women. According to Nicky Cowper from the company, the most important thing when choosing a hat is that the fit is right. “Comfort is so important,” she claims. “You need to be able to wear it all day and hopefully for seasons to come.”

Two sisters are behind Hicks & Brown. It stocks a wide range of hats. The Wingfield Trilby (£149) comes in navy and brown, and features antique brass detailing on the ribbon. A firm favourite is the Suffolk Fedora (from £89) that the Princess of Wales has been photographed wearing.

Ladies’ Day

Another name sure to be in the running at Cheltenham is Holland Cooper. It offers a number of trilby hats to choose from, all £129 and handcrafted in England in one of the UK’s oldest factories. A sporting hat requires confidence, so when looking for a lid make sure it is top drawer.

A Holland Cooper grey trilby

However, sometimes the weather can dampen spirits. Fear not if a deluge is forecast: there are some very smart waterproof hats about. Walker and Hawkes waxed Thelma hat is available in a wide range of colours and features a pretty knot and a tartan bow.

Click here to find out more about stretching favourite hats or read our history of the topper.