Guarantee your hat-iness at the Epsom Derby

By Helena Sheffield - author of The Art of Wearing Hats, March 30, 2016

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.


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…


Fascinator and Hatinator

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.


Pillbox Hats

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.


Wide Brim Hats

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.



Now that you’re well and truly hat-spired, you may be wondering what the key hat trends of 2016 will be. We’ve already seen a movement away from fascinators in recent years as people are gaining confidence and donning more daring headpieces (hurrah!). As we move into racing season now, it’s all about florals: these hats are often in muted pastel colours with subtle layers of flowers incorporated either in the fabric pattern or as embellishments. There is more emphasis on the height and size of the flowers this year, with bolder blooms taking preference over shrinking violets. The contrast between the soft colours and statement blossoms creates a sophisticated balance.


Choose a theme for your outfit. This can be a colour, a fabric, a style (particularly if you want a vintage flair – consider which era you’re going for), and will help you begin your search. You may change your mind once you’ve found The Hat, but it gives you a good place to start.

Determine your face shape. Look at our guide at the bottom of the page to see which hats best suit you: narrowing down your search is key at this point, and knowing what suits you as well as what you like will save time.

Begin with the hat. It’s much easier to match the colours of a dress to the hat than the other way around.

Size matters. If you’re not used to wearing hats, don’t feel pressured into wearing something big. The Derby accepts hats or “substantial fascinators”, and the last thing you want is to be distracted by an overbalanced hat all day. Start looking at pillboxes and sinamay berets. These are small, often simple, and perch on your head without getting in the way.

Try everything on. Or, at least, as much as possible. It’s really the only way to understand what should be avoided at all costs, what makes you look positively magnificent, and everything in between.

Check your sanity. Will there be an outfit that goes with this hat? Chances are there will be, but once you’ve settled on The Hat just ask yourself whether you’ll find a dress that really does match its gorgeous acid green tones. Yes? Then all that’s left to do now is sit and stare at it with pure glee. Congratulations, you’ve finally found your true love. 

What hat to wear at Epsom

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