4 tips that finally gave me confidence to wear red lipstick at 49


As her 50th birthday approaches, beauty editor Donna Francis finally found the confidence to wear red lipstick thanks to this advice.


Donna has found the confidence to wear red lipstick in her forties
Donna Francis
Donna FrancisUS Beauty Editor At Large, Second Act
November 12, 2025
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For years, I’ve admired red lipstick on other women. From when I was younger, I remember longing to wear it like Madonna in the 'Who's That Girl' video - but being called rubber lips at school put me off.  When I reached my twenties and the grungier more pared-back Kate Moss era was taking hold, red lips felt too bold and bright. I didn’t want to draw too much attention to my lips. Red felt a bit too sexy and so I just stuck to my nude lip pencil and lip balm combo. But something shifted when I hit my forties. I'd made peace with my face and my rubber lips. And age had invited some experimentation into my makeup bag. I felt open to trying brighter makeup. 

In her early 40s, Donna began to wear red lipstick
In her early 40s, Donna began to wear red lipstick

At the same time, I ditched the safe black outfits in my wardrobe and introduced more colour. I suddenly wanted to embrace the confidence I saw in other women who opted for brighter style options and red lipstick was a fast-track way of updating my look. Angelina Jolie, Taylor Swift, Adele - I realised that wearing red lipstick was actually an ageless trend because it provides instant lift to your face. But how should I wear red lipstick as an almost 50-year-old woman? I asked my friend and celebrity makeup artist, Donna May for her advice and she completely changed the way I approach it. "Most women feel nervous about red lips," says Donna. "Not because they don't love the look, but because red can feel bold and a bit intimidating. The idea that red is 'too sexy' is so outdated - I think it looks super sophisticated."

Celebrities like Angelina Jolie and Taylor Swift prove that the red lip is a timeless and ageless © FilmMagic
Celebrities like Angelina Jolie and Taylor Swift prove that the red lip is a timeless and ageless

How to wear red lipstick in midlife 

1. Start with a matte red

Donna's first piece of advice instantly made red lipstick feel more wearable for me. "Start with a matte red," she told me. "It's less glossy, so it feels more subtle and less in your face." And she was absolutely right. Swapping shine for a soft matte finish looks effortless and sophisticated. 

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2. Find the right red for your skin tone

If you've ever tried red lipstick and thought it didn't suit you, you’re probably wearing the wrong shade. Donna broke it down perfectly: "If your veins look green underneath your skin and you tan easily, you have warm-toned skin, so you should go for orange-based reds. Cool-toned skins that burn easily tend to have veins that look blue," Donna added. "These should reach for blue-based reds with pink or berry undertones - think Nicole Kidman." Even though I have a warm, almost olive skin tone, I found that I preferred to wear a more pink, berry-based red shade, even though she insisted the orange tones suit me.  But Donna says that's fine as long as I feel good wearing it. "You have neutral tones, so you’re lucky that you can wear both!" she told me. 

Donna has a neutral skin tone so feels confident wearing red lipsticks with both orange and berry under tones
Donna has a neutral skin tone so feels confident wearing red lipsticks with both orange and berry under tones

3. The pro trick to make red last

The one thing I have noticed since wearing red lipstick is how messy it can get. Especially when you're not used to wearing colour on your face. It smudges. It stains. It bleeds. But Donna has a secret for keeping it looking flawless all day. "Apply a little foundation to your lips with a brush first, then dust it lightly with translucent powder, and then apply your lipstick," she says. It's a simple prep step that makes all the difference, and will help your red stay put through the day.

I'll admit, I still don't wear red lipstick on a daily basis, but when I do, I wear it very simply - with almost no makeup on my eyes - just one coat of black mascara. It definitely helps to give me an extra jolt of confidence before I walk into a room. 

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