The best make-up looks to match with occasion headwear

Jennifer Lopez attends the 61st Annual Grammy Awards in 2019
Jennifer Lopez attends the 61st Annual Grammy Awards in 2019 - Getty

Ooh, I love a hat. Straw hats, fedoras, fun vintage numbers (although my husband doesn’t really get my 1950s yellow bucket hat with the nylon daisies). But when it comes to a special occasion, say a wedding or Royal Ascot, not only does your choice of headwear require forethought, so does your make-up. Because it makes a big difference to the overall impression.

For advice, I spoke with make-up artist Amanda Clarke, who has worked with countless celebrities including Dame Judi Dench and Rachel Weisz. She also preps guests for events, including Royal Ascot, which takes place later this month. Who better to give some top tips for three of the most popular occasion-hat shapes?

First up, let’s talk the big brim, one of my faves. It’s a style that has been a winner for decades – think Audrey Hepburn in Breakfast at Tiffany’s and Jennifer Lopez in a huge-brimmed white hat at the 2019 Grammys. Both of these style icons played up their eyes, either by going graphic or smoky.

Audrey Hepburn as Holly Golightly in Breakfast at Tiffany's, 1961
Audrey Hepburn as Holly Golightly in 'Breakfast at Tiffany's', 1961 - Getty

‘A bold eye works beautifully,’ says Clarke. ‘The brim casts a shadow over your eyes, so if you don’t emphasise them, they tend to disappear. You don’t have to go smoky, though that can certainly look alluring, especially if you use lots of mascara or even faux lashes. You can up the drama with jewel-coloured eyeshadow and eyeliner. Have fun with it.’

Whatever approach you take, you’ll need more than one eyeshadow shade (usually lighter for the lid, and darker for definition both above and underneath the eye), so treat yourself to a quad palette – the brand will already have considered how the shades hang together. Guerlain Ombres G Eyeshadow Quads (£65, Guerlain) offer some amazing options.

Guerlain Ombres G Eyeshadow Quads, £65, Guerlain
Guerlain Ombres G Eyeshadow Quads, £65, Guerlain

 Guerlain Ombres G Eyeshadow Quads, £65, Guerlain

‘Remember, keep your eyes as the statement, which means going fairly neutral on your lips,’ advises Clarke.

Next, the pillbox, a super-staple that started turning heads in the 1930s, reaching a pinnacle of pizazz when sported by Jackie Kennedy. Which way to go with this perky little number? ‘Because people’s eyes will be drawn to the hat perched high, bring balance with bling on the lips to anchor the look,’ says Clarke. ‘In terms of colour, there are three schools of thought: simply go for your favourite lipstick shade that suits your skin tone; go matchy–matchy [obviously not if you’re wearing green], with red, pink and purple working well; or go for the clash, so if your hat is scarlet, try zingy tangerine lips.’

Jackie Kennedy was known for her hats
Jackie Kennedy was known for her diverse hat collection - Getty

Finally, there’s the fascinator – sometimes quirky, sometimes coquettish, often with a veil. ‘The veil creates softness over the face, so you want to bring some structure to your features,’ says Clarke. ‘An obvious choice is strong lips, but that can look a bit obvious and outdated. Instead, focus on your brows, fluffing them up and filling them for definition, then go to town with deliciously dewy blusher, targeting the apples of the cheeks. A touch of nude but lush lipstick complements the elegant prettiness of a veil to perfection.’

As for other practicalities, to avoid transferring sweat and make-up from your forehead on to your hat, there are hat-protecting peel-and-stick strips (no, I hadn’t heard of them either, but what a good idea). A number of examples are available on Amazon.

Lastly, as Clarke recommends, for a big event, have a run-through. This way you can experiment and see what works, so on the big day you’re not in panic mode and can place your hat with aplomb. Then sip a glass of something sparkly.