Choosing a Hat For That Special Occasion: 9 Tips From an Expert Milliner

Get your game face on with a hat that’ll turn heads; here’s how to choose the best one for you.


Whether it’s a wedding or a day at the races, you’re probably already trying to figure out what you can wear to look both stylish and within the strict dress code.

Outfit aside, you’ll want to top your look off with a head-piece that screams style.

But if the hat department of your local store has got you scratching your head, fear not – because we’ve got an easy guide to find the top topper for you.

Expert milliner and Experience host Sarah-Jayne, who trained with the masters and has dressed the heads of ladies from London to Paris, has teamed up with Airbnb to guide racegoers through the minefield with her Hat-Etiquette guide.

Here’s what you need to know:


  • Whatever hat you choose, don’t go overboard with accessories; a statement necklace with a detailed headpiece will look too fussy so opt for one or the other.


  • Remember that for the Royal Enclosure at Ascot your hat must also meet the strict dress code. For VIP tickets, fascinators are a no-go and any headpieces must have a solid base of at least 10cm- you have been warned!


  • If you’re looking to turn heads at the races, choosing a brightly coloured fascinator will definitely make you stand out. Go for block colours in a vibrant shade off-set with jet black for real the wow factor.


  • If you have a long face, balance out the length by wearing a hat that sits to the side with a wider brim. A squarer face shape is often softened by rounded styles or a veil – don’t be afraid to try a variety of styles and see which works best for you.


  • It is personal choice which side to wear your fascinator, but try wearing it on the side where your hair parts, with the fullest side of your hair on show.


  • If you’re petite, a delicate feather fascinator or a smaller-sized headpiece tilted to one side, which isn’t wider than your shoulders, will work well.


  • For those with a round face shape, balance your face with a headpiece containing long feather quills or sinamay twists. They add height and elevation, elongating your face.


  • Heart or oval-shaped face? You’re lucky enough to be able to wear almost any shaped hat so be adventurous and go for something OTT and outrageous.


  • Modern disc-style hats, like pill-box fascinators, are soaring in popularity. These are secured in place by a comb or on satin covered hairbands that can easily be disguised in your hair.



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