Between the leaves falling, the temperature dropping and a transition from Birkenstocks to boots, seasonal shifts are always a good time for change. And this goes double for trying something new with our beauty routines. 

So, as we move from autumn to winter – with darker nights and hot water bottles in tow – may I humbly suggest we commit to trying one new thing. Perhaps, a deep, dark winter lipstick, say?

I know wearing dark lipstick can feel like a bridge too far if you’ve only ever dabbled in natural, nude or light lip colours. Or, if your lip travels have only taken you so far as a pot of Vaseline. Without guidance, it can feel like a complicated blend of vampy purples, dark browns, deep reds and stark blacks. 

For example, did you know that your skin’s undertone can determine the shade of dark lipstick that’s best suited to you? Or, that identifying your undertone is as easy as pinching a sheet of A4 from the printer and holding it up to your face? Well, if you didn’t, don’t worry. That’s what we’re here for.

So, to make your foray into dark lipstick a success story, follow this expert guide to finding, applying and maintaining a dark lip. 

“To identify your undertones all you need to do is hold a white sheet of paper to your face,” explains global makeup artist Sarah-Jane Froom. “If you look more yellow or gold, it means you have an olive/golden undertone. If you look more pink or red, it means you have a cool undertone. If it’s neither, then you have a neutral undertone.”

“Those with olive and gold undertones look better in gold jewellery and cool undertones look better in silver. Have a think about which ones suit you the best to help identify yours.”

“First things first, look at your skin undertones in order to decipher the right dark lipstick tone for you,” advises make-up artist and beauty editor Lauren Patricia Maybank. Then…

If your skin has yellow, olive or gold undertones

“Women with warm (yellow, gold, olive) undertones should look for mauve, raspberry, burgundy colours – something like a summer pudding with a hint of warm undertones. Lip and Cheek stick in Rosy Brown or Chocolate Mocha from Jones Road Beauty is a great way to achieve a lightweight wash of colour.”

If your skin has pink undertones

“Cooler undertones (pink) can use blue-based berries, deep blackberries, coffee, oxberry and plum tones (as demonstrated by Lily Collins). Nude by Nature Lipstick 07 in Deep Plum is a good example of this, too.” 

If your skin has neutral undertones

“If you have neutral undertones or are just unsure – have a play about! I personally think it doesn’t really matter so much on the tone, it’s more ‘go big, go home!’ so intensity plays a big part and wearing the colour with confidence is the other.”

“Grape Vision Flush Multi-Purpose balm from Danessa Myricks is a great way to play with a bold, alternative colour – it’s a rich purple – and if used lightly on lips and cheeks it suits a variety of skin tones.”

“For dark colours, I recommend applying with a brush to give you more control,” says Froom. “I’d suggest the Bobbi Brown Brush for perfect application. When applying your lipstick, make sure to hold your lips taut while you do so. This will ensure that colour is deposited on every part of your lip.

“You don’t want to see creases where the lipstick hasn’t been applied when you talk or smile. The next step is to press with a tissue. This will get off any excess and take any oil out so you get a great stain. Then, reapply lipstick. This will keep it in place all day.”     

Remember, too, that a carefully applied lip liner can also make a huge difference to the appearance of your dark lipstick.

“It keeps the lipstick stop bleeding and provides more dimension to the lips,” explains make-up artist and founder of Vesta London Beauty, Vesta Boateng. “It shapes and carves the lips to prepare for lipstick application.” 

“A modern way and easy way of not feeling intimidated by a darker hue is to treat it as a ‘stain’,” says Maybank. “Use your finger to place into the fleshiest part of the lips and dab so it gives a ‘wine-snogged’ effect. You can then add a similarly toned lip-liner to ensure the colour doesn’t bleed – and to add depth to the outer corners.” 

“Dark lipstick can most certainly feel intimidating. For beginners, I would suggest starting out with shades that are one or two shades darker than your natural lip colour and then gradually working your way up to a dark colour you feel comfortable in,” says Boateng.

“In order to not feel or look washed out, the key is to wear a blusher of the same ‘family’ to marry the look together,” explains Maybank. “If you’re going for a deep berry shade – use something along the same colour line. So, a plum, or a pink erring on the darker raspberry side. Or just daub a small amount of the same lipstick you have used onto the apples of cheeks and blend out towards the temple for a beautiful flush – nothing like a good old multi-task.” 

Of course, at the end of the day, the way you pair (or don’t) your dark lipstick with your look is a completely personal choice. There’s no right way to wear makeup, as Froom reminds us:

“To find the right shade of browns, reds, blacks, purples is just a personal preference. If you have the right undertone, then you can go as vampy as you like. You may just need to add a touch more bronzer or blusher to warm the rest of the face. Keep the balance,” says Froom.

“Exfoliate your lips regularly,” advises Boateng. “Maintaining a smooth, soft application for a dark lip is key. If your lips are not well maintained lipstick can make the lips flaky and dry which we don’t want, especially in the upcoming winter months.”

Now you’re up to speed on how to wear dark lipstick (and how to make the jump if you’re just starting out), let’s find the vampy, winter-appropriate one for you. 

Main image: Getty