There was once a time when it was considered the height of vulgarity for a lady to be seen in public without her hat; it was a symbol of status and propriety. And, oh boy, didn’t they look grand, with their hair swept up and a dash of rouge. Things may be different now, save for a few bona fide hat fans — Roisin Murphy, Grace Jones, Anna Piaggi — but with Ascot and wedding season on the way, hats are having their annual moment in the spotlight.

“When I first started making hats, young people had given up wearing them because they felt they were too conformist. They are no longer symbols of conformity, but highly individual acts of rebellion,” argues the virtuoso milliner Philip Treacy. That goes for the make-up, too. A brim, a veil, a bejewelled fascinator — all require you doing something different with your make-up and even your hair. So, here’s your guide to foolproofing what lies beneath.

THE PILLBOX

The pillbox hat has a quirkiness that allows you to go all out with hairstyling. “You can let your hair go wild. Either go really big, or tie it back for a super-sophisticated look,” says Grant. To achieve this style, above, Cave made two ponytails, one above the other. “Plait the lower pony, then attach the hat with its elastic band. Plait the other one, twist them both together and pin to the side of the head,” she says.

“The trick is not to give up; if it doesn’t look right, try again.” If your hair is the main draw, go easy on the make-up. “Add Dermalogica Sheer Tint Moisture SPF15 [£23] to cheekbones. The glow reflects the hat’s sparkle,” says Cave.

Hat, £497, by Victoria Grant; victoriagrant.co.uk. Face and Body foundation, £22.50, Pigment in Polished Ivory, £15, Mineralize Skinfinish in Dark and Gold Deposit, £17 each, Eye Shadows in Print and Orange, £10 each, Technakohl Liner in Graphblack, £11, Lipstick in Pink Cabana (limited edition), £11, all by Mac

THE BOATER

“Wear the boater cocked at an angle, perched high on a mountain of hair. Concentrate on creating an interesting silhouette,” says the milliner Victoria Grant. “Keep make-up clean and eyebrows groomed. Spray hairspray on an old toothbrush and brush through the brows, then go over with eyebrow powder by Laura Mercier to enhance the natural shape,” says Charlotte Cave, who styled the hair and make-up for this shoot. “With a shorter-brimmed hat, you can pull off a feline eye. It doesn’t have to be a heavy graphic: a smoky hint of lovely blue-grey would balance it out,” adds Terry Barber, head of make-up artistry at Mac. “This hat is also great if you are a hair-down kind of girl,” says Cave. “It’s shabby chic with edge. To get this look, dry hair upside-down, set it in heated rollers or finish with tongs. Then go Elnett mad.”

Red Boater, £250, by Marc Jacobs. Tinted Moisturiser, £32, Bronzing Powder, £25, Matt Eye Colour in Fresco, £18, Brow Powder Duo in Ash, £20, all by Laura Mercier; 0800 123 4000

THE WIDE-BRIMMED HAT

“You have to think about the whole package. If you’re wearing a wide-brimmed boho hat, the look should be softer,” says Barber. “Focus on the lower half of your face. Sculpt the cheekbones so the light catches them and add bright lips if it feels right. Highlight the centre of the chin and bring out the jaw a little using a translucent powder or Mac Strobe Cream [£20].” Here, Cave set the drama around the eyes. “Romantic doesn’t mean boring. Use bold colours on the eyes against a backdrop of soft grey for definition. Bronzed cheeks add a 1970s touch, and soft pink lips keep it kissable. Keep hair loose and carefree for a modern edge.”

Hat, £99, by Whiteley, from Fenwick. Eye Shadows in Orange and Print, £10 each, Pigment in Polished Ivory, £15, Face and Body foundation, £22.50, Mineralize Skinfinish in Dark and Gold Deposit, £17 each, Lipstick in Pink Cabana (limited edition), £11, all by Mac

THE FASCINATOR

“This look is all about the lips. Keep them matt for a classic vintage face in keeping with the 1940s-style hat,” says Cave. “Cheeks should be bare — just apply a little foundation. To make the lips pop, add a touch of foundation first, then use lip liner to outline and fill them in. For a flawless finish, go over with a deep red lipstick. Bring the look up to date with individual false lashes on the outer edges of the eyes and create strong brows to carry through the veil.” For hair, simple, clean lines work best. “Balance your hair with your fascinator. Wear it to the opposite side or sculpt it into a beautiful, tidy up-do,” says Grant.

Fascinator, £720, by Chanel. Lift Lumière foundation, £34, Ombre d’Eau shadow in Source, £21, Sculpte Sourcils in Brun, £15.50, Le Crayon Lèvres in Praline d’Or, £15.50, Rouge Allure lipstick in Passion, £21.50, all by Chanel. Carmex, £2.50. False eyelashes, £12, by Shu Uemura

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