Guarantee your Hat-iness at the Epsom Derby – Part 1

Have you ever had that dream when you turn up to an occasion and aren’t comfortable that what you’re wearing will fit in.

We’ve all been there. There is nothing quite so daunting as choosing the right outfit to wear at any party, let alone an event you might not have been to before. If finding a dress was envisaged as a challenge, the hat could be deemed a step too far!

But never fear! We have enlisted the help of hat connoisseur and author of The Art of Wearing Hats, Helena Sheffield, to give us all a helping hand. Read on for her guide to all things hat-related.


Your Epsom Derby Hat Guide

The first hunt for a new hat can be daunting. The options are endless; the styles, colours and variations dazzling yet insurmountable. How to even begin? A breakdown of the key styles worn to the races would be a good place to start…


The lines between the two can blur, but a general rule is that a fascinator is more an ornament that only partially covers the head and is held on by a clip or a small headband. A hatinator is larger and tends to sit more comfortably on the head, although is often supported by a larger headband. A hat-wearing novice may worry that hatinators are too precarious, so look out for compact designs that stay close to your head and have fewer trimmings.


No, not the wool hats traditionally worn by French artists, but intricately-woven and beautifully-decorated head pieces worn at formal occasions. Made of sinamay, they’re an excellent option for those who want almost to forget they’re wearing a hat. There’s a vast amount of choice of colour and style, and if you’re more aux fait with hat-wearing, look out for berets with bigger embellishments – feathers, flowers and veiling in particular.


This really is renowned as the hat for those who don’t like wearing them – Jackie Kennedy admitted her aversion to hat-wearing (unimaginable!), inspiring fashion designer Halston to reintroduce the pillbox as a solution. It sits higher on the head than a beret (especially good for round faces, but may jar with an oblong face), and while often made of felt or velvet, can be found in lighter materials such as straw and sinamay ahead of the summer season.


Depending on the size and shape of a wide brim hat these can come supported by a headband, in which case they sit primly atop your head, or can be worn like a traditional hat. Square- and oblong-shaped faces work particularly well with hats that have the fluid line of a wide brim hat that sits properly on your head, while round faces can benefit from a taller hat, as it helps elongate them. Wide brim hats allow for stunning creativity, but don’t underestimate the beauty of a simply-adorned headpiece: sometimes the quieter are the most breath-taking.

*Illustrator: Sian Tezel


Now you know all about the hat options available, you’re almost ready to become a Furlong Fashionista at the Investec Derby Fesitval this year. Head over to Part 2 to find out what’s hot this season and which hat will best suit your face shape with Helena’s top tips.

The Art of Wearing HatsThe Art of Wearing Hats

Hat connoisseur, Helena Sheffield, boasts a collection of somewhere over 40 hats!

Complete with tips on where to buy them, how to wear them, who wears them best, and the tricks of the trade, The Art of Wearing Hats is the ultimate pocket guide for hat novices and afficionados alike.

Buy it here.

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