‘Wear what makes you happy’ Trinny Woodall’s ultimate guide to ageless dressing

Fashion rule book? Rip it up, says YOU’s Contributing Editor Trinny Woodall. In her ultimate guide to ageless dressing – with more than 70 brilliant tips – she shows us how to look great and feel amazing every single day.

I’ve been doing makeovers for 30 years, but I’m still surprised when I hear women tell me that they can’t wear certain styles, colours or fabrics after the age of 50. I’m here to tell you to rip up that old-fashioned rule book.

Trinny Woodall
Dan Kennedy

Fashion no longer has age limits – teenagers and their grandmothers wear the same pieces, from the same store, just styled in different ways. Today it’s about embracing ageless dressing: choosing clothes that flatter in sophisticated fabrics, knowing your body shape and what colours suit you best. It’s also about still daring to take risks. You don’t have to look conservative just because you’re in your 60s, 70s and beyond and you can – and should! – still shine at any age.

For decades I was led by style rules, but more recently I’ve followed one mantra when it comes to clothes: ‘Does it make me happy?’ If you feel happy in what you’re wearing, you will radiate happiness to those around you and that’s what dressing should be about. So here, over the following pages, I’ve shared my favourite summer outfits; they’ve brought me that sense of happiness and I hope they’ll do the same for you.

Start with a go-anywhere dress

1. We all have a long dress that we bought for an event but now only wear once a year. Well, it’s time to give it a new lease of life. There’s great freedom in a long, wafty dress in a chic fabric that can be worn casually for day and glammed up for evening. I like a style with a high neck because it frames the face and maximises the colour impact – cornflower blue suits me best, but choose the right hue for you. To take your dress from day to night, add statement jewellery – a long necklace, earrings or a cocktail ring would also look great.

Trinny Woodall
Dan Kennedy

2. I like my arms and am happy showing them off, but if you prefer keeping yours covered pick a dress with sleeves.

3. Choose a maxi dress in a colour that makes you look the most ‘alive’.

4. Team your maxi with a pair of white trainers (if it’s a dress you usually wear with heels, choose platform trainers). It’s an instant moderniser.

5. Dress, £185, essentiel-antwerp.com. Ring, £98, merola.co.uk. Trainers, £80, frenchconnection.com. Necklace, Trinny’s own, for similar try johnlewis.com. Blazer, Trinny’s own, for a powder-blue jacket go to jigsaw-online.com.

Trinny Woodall
Dan Kennedy

6. My blue Zara jacket is 15 years old but goes perfectly with my new blue dress.

7. A crossbody bag or wicker tote keeps the look casual for day time.

8. Bag, £150, raefeather.com 

9. Blazer, £275, reiss.com 

10. Dress, £120, stories.com 

11. For a day look, add a jacket in a slightly paler tone than your maxi.

12. Dress, £150, uterque.com 

13. Dress, £395, LoveShackFancy, beachcafe.com 

14. Dress, £55, weekday.com 

15. If you are an hourglass shape or want to show off your cleavage, choose a maxi with a V-neck and that nips in at the waist.

You’re never too old to wear white

16. Why do people think it’s only for the young and petite? Nonsense. The trick to wearing white well? Think layering and textures. Sheer is also a playful way to add white to your look as it’s not about showing off skin, just creating the illusion of doing so. Here I’ve teamed my favourite Zara gilet with a statement top. Keep your trousers well-cut, but neutral. Finish off with a metallic shoe (a bit of shimmer goes with everything).

Trinny Woodall
Dan Kennedy

17. We all know a red lip rocks with a black dress but it looks fab with white, too.

18. Blouse, £35, oasis-stores.com 

19. Mix fabrics such as broderie anglaise with silk – it will give your outfit definition.

20. Dress, £180, uterque.com

21. Don’t fear sheer! You can always add a cami underneath.

22. Trousers, £34.99, hm.com

23. Clothes, Trinny’s own. For a similar blouse try nastygal.com. For a long waistcoat, go to mango.com. Karenmillen.com sells white wide-legged trousers.

24. Jumper, £85, frenchconnection.com

25. Contrast a flowing top with crisp tailoring to keep it smart.

Update your summer wardrobe with the perfect white shoe

26. Sandals, £30, next.co.uk

27. Flats, £16, tuclothing.sainsburys.co.uk

28. Shoes, £62, office.co.uk

If you’re feeling invisible…

29. Wearing bright colour from top to toe gives you presence when you enter a room. Azingy silk shirt with matching pyjama-style bottoms is one of my staple looks. Not just the more modern way to wear trousers, its forgiving cut skims my legs, while the contrasting waistband and loosely tucked shirt highlights the waist. 

Trinny Woodall
Dan Kennedy

30. When wearing a strong shade, tone down lips but swirl on lots of blusher so your face has colour, too.

31. Clothes, Trinny’s own. For a similar shirt and trousers, try serenabutelondon.com. Superga.co.uk sells white platform trainers.

Top-to-toe colour too much? Try a splash with these

32. Flats, £55, charleskeith.com

33. Sandals, £29, topshop.com

34. Dress, £350, Cefinn, matchesfashion.com 

35. Bag, £8, tuclothing.sainsburys.co.uk 

36. Team different colours together – I’d add neon jewellery to this jumpsuit.

37. Jumpsuit, £298, meandem.com 

38. Top, £45, and skirt, £69, cosstores.com 

39. You may have noticed I’m a huge fan of white trainers – they go with everything and always up the cool factor.

40. Trainers, £130, Michael Kors, houseoffraser.co.uk 

41. Dress, £229, tedbaker.com 

42. Dress, £139, baukjen.com 

43. Blouse, £165, reiss.com 

44. Dress, £625, delavali.com 

45. If you prefer separates, try tailored trousers with a flattering silk top for a sleek, chic look.

46. Trousers, £625, Stella McCartney, net-a-porter.com

Ageless elegance for any occasion

47. This is the ultimate summer dress. Both pretty and chic, it will look the part at every formal event in the diary, from weddings to the races. For outdoor dos, wear with platform heels as stilettos will sink into grass. The broderie anglaise fabric also makes it a winner – far more forgiving than lace, this gives the impression of being sheer but doesn’t reveal so much skin.

Trinny Woodall
Dan Kennedy

48. A strong lip will hold its own against a colourful print.

49. For timeless chic, an occasion dress should fall to just above the ankle, which is the most flattering length for any woman.

50. Dress, £740, Zimmermann, net-a-porter.com. Shoes, £620, aquazzura.com  

The accessories

51. Every woman needs a metallic shoe in her life, as it will go with every look.

52. Shoes, £60, aldoshoes.com

53. Hat, £20, monsoon.co.uk

54. Don’t be afraid of wearing statement jewellery with a print dress. Go for dazzling earrings or a dramatic ring.

55. Earrings, £48, butlerandwilson.com 

56. Ring, £105, monicavinader.com 

57. Hat, £13.99, hm.com 

58. Top, £95, reiss.com

59. A long shimmery skirt is the foundation for my summer capsule wardrobe.

60. Dress, £230, Bec & Bridge, harveynichols.com 

61. Skirt, £59.99, mango.com 

62. Wedges, £35, Office, houseoffraser.co.uk

63. Dress, £38, dorothyperkins.com 

64. Add statement jewellery to up the drama – just make sure it’s of the same tonal palette.

65. Necklace, £50, anthropologie.com 

Shimmer flatters everyone

66. And sparkle is not just for the party season. Shimmer lifts every outfit and will make a casual ensemble look sophisticated. This skirt is my summer friend – I can wear it anywhere, from running errands to going on holiday. Add a white jacket for a meeting or smart dinner, but make sure it’s short-waisted and has one button. Finish off the look with a statement lip for a modern ‘undone’ look. 

Trinny Woodall
Dan Kennedy

67. Vest, Trinny’s own, for similar try reiss.com. Skirt, around £600, mariefrancevandamme.com. Trainers, £80, frenchconnection.com. Necklace, Trinny’s own, jcrew.com sells similar designs 

…and sequins really add edge to your basics

68. When wearing long jackets, choose one that extends to your trouser hem for a polished finish.

Trinny Woodall
Dan Kennedy

69. Clothes, Trinny’s own. For a sequined jacket, try zara.com. For a white T-shirt, visit michaelstars.com. Reiss.com sells black tailored trousers. Wedges, £425, clergerieparis.com 

70. Instead of a tailored jacket, throw a sequined kimono or gilet over your outfit.

71. Kimono, £89.99, zara.com

72. Shirt, £45, riverisland.com

For a beauty reboot

Time to rethink your routine? Here are my tips for shaking things up.

Skincare

73. I swear by this holy trinity of ingredients: SPF, vitamin C and retinol. Heliocare 360 Gel Oil-free SPF 50 (£27, skincity.co.uk) is my sunscreen hero as it is very light and non-greasy.


For the collagen-boosting, skin-brightening benefits of vitamin C, try Garden of Wisdom Vitamin C 23% Serum and Ferulic Acid (£10, victoriahealth.com), or invest in my favourite, SkinCeuticals C E Ferulic (£135, skinceuticals.co.uk).
For retinol, which resurfaces the skin by accelerating cell turnover, Indeed Labs Retinol Reface (£19.99, boots.com) is a great starter product. I also like AesthetiCare Retriderm Vitamin A 0.5% Retinol Skin Serum (£43, facethefuture.co.uk).

Hair

74. Rejuvenating hair can be as simple as changing your parting. If you dye your hair, does your colour still suit you? Would lowlights soften your style?


If you don’t want the cost of constant visits to the salon, try Color Wow Root Cover Up (£28.50, colorwowhair.com) for a quick fix. But giving your hair a refresh doesn’t have to mean dyeing it.

There are some great products for brightening grey hair: Redken Color Extend Graydiant range (from £15.50, lookfantastic.com) reduces brassy tones and Philip Kingsley Pure Silver Conditioner (£22.50, johnlewis.com) boosts shine.

Make-up

75. Base-wise consider using lighter cream-based formulations instead of foundation and powder, which can be unflattering. I’m never without my own Trinny London BFFCream SPF30/Skin Perfector (£35, trinnylondon.com), which brightens skin but also gives coverage.

To update your look further: swap bronzer for blusher, which looks fresher, ditch eyeliner, which is too harsh as we get older, and smudge a cream-based eyeshadow along the lash line.


Lip liner can also be put aside – instead use cream lip colours applied with a fingertip to create a softer, more ‘undone’ mouth, as I’ve done in my sequin look, using Trinny London Lip Luxe in Eugenie, £22.