I’ve been staying with my friend Helena while I’ve been in NYC, and it’s been everything that you would hope a week with one of your closest friends would be. It’s like a slumber party every night of the week, and I feel so lucky to have such awesome friends who are willing to watch Reign with me and get way too into talking about it afterwards.
I’ve been teaching Helena about makeup while we’ve been hanging out, and it’s been so much fun. I really love playing with makeup, and I REALLY love teaching people new things, so this works out really well for both of us.
One of her biggest questions was about red lipstick. As a natural redhead, Helena was always pretty sure that red lips were a makeup look she was just eternally banned from trying out. But I say that is nonsense! Redheads look totally awesome in red lipstick, but as with everything, one just has to get the right shade.
So I decided that we were going to haul ourselves into Manhattan (I KNOW, MY LIFE IS SUCH A TRIAL) and find her some totally beautiful red lipsticks. After we talked a little, we determined we'd find her a light, semi-sheer red that she could wear every day, and a darker red good for parties and being fabulously vampy.
So we set out to find her Magical Reds--those lipsticks that make you look and feel like the hottest babe who ever lived.
If you have red hair and would like some red lipstick pointers, read on! And if you don’t have red hair but are looking for some general guidance, read on anyway, because these tips are useful for everyone!
Consider the finish.
Helena already told me that she wanted a red that was a little lighter and good for daytime, and a heavier red that is good for going out at night. This gave me an excellent starting point for finding lipsticks, because I knew what she needed the products to DO.
Ask yourself what you’re looking for. Do you want a lipstick for special occasions? Do you want a red that will work for every day? What is your general makeup style? Are you serving bare-faced minimalism or retro burlesque-inspired realness? All of these things will affect the TYPE of lipstick you are looking for.
Here are a selection of lipsticks that I have with me, arranged from lightest (basically a tinted lipbalm) to heaviest (a totally matte lip pencil).

These are all reds, but they're all very different intensities and will all look totally different on one’s face. So you can see that it’s really important to think about the finish of the lipstick that you’re looking for!
Consider the wear.
Think about your life. Do you want a lipstick that lasts all day without touchups, or are you cool with taking a break every few hours to reapply? Just remember that very sheer and super-long-wear products BOTH come with downsides: very sheer lip colours come off quickly, and very long-wear lip colours can be extremely drying. So if you’re down for either, just be prepared.
Helena’s lips get dry, especially in the winter, so she nixed all discussion of very long-wear lip colours. We tried on some very sheer red lipstick, but even though it looked adorable, it didn’t give her the amount of colour that she was looking for.
Warm or cool?
This is a crucial question for everyone, but especially for redheads. Getting the temperature of the lipstick wrong can result in hair and lips competing, rather than complementing one another, and we don't want that!
I wish there was a blanket rule I could issue here, but there isn’t; there is so much variation between red hair colour, skin tone and number of freckles, personal preference, and ALL of this affects whether you pick a warm or cool-toned red.
A refresher: Warm reds are those with orange or yellow tones in them, and cool reds are those with blue or purple tones in them. This can be hard to picture, so here is a visual:
Both of these colours are about the same shade, they just have different amounts of yellow and blue in them. I strongly prefer cool colours, whereas Helena prefers warmer ones.
I find that a lot of the advice about who should wear cool versus warm colours is kind of not very good. There are no hard and fast rules about skin tones that MUST BE FOREVER LIMITED to warm reds or cool reds. It mostly has to do with what you like best. And there is only one way to find out which general category you like best, and that is...
Try everything on!
No shortcuts! Once you’ve decided what you're looking for and you have a general idea of the finish you want, try on a bunch of colours by multiple brands. Sometimes the ones that look the best on you might surprise you. Do not judge until you see it on your face!
So now let’s talk about Helena’s lipstick journey…
After we’d tried the Clinique Almost Lipstick and she’d vetoed it, I suggested we check out the Dior Addict Lipsticks, because they are totally some of my favourites. They're lightweight but pigmented, sometimes with a bit of shimmer in them, and come in a wide range of colours. They always look really fun, but also sophisticated, and I knew this was something Helena wanted. She teaches, and therefore likes to look pulled-together but also relatable.
Here she is wearing Rock N Roll, which is a warm, sheer red with a little sparkle.
This almost never happens, guys, but she decided right there and then that this was the red she wanted for her daily wear. It was the first colour I picked for her. Talk about awesome!
For a more dramatic lip colour, we skipped over to MAC where she tried out a satin-finish lipstick. Russian Red, which is a warm-toned brick red, looked totally fantastic.
It was a LITTLE too drying for her lips, though, so we hopped back to Sephora and I pointed her to my ride-or-die favourite lip colours, NARS Velvet Matte Lip Pencils. I made her try on Dragon Girl, which looked totally STUNNING on her…
…but when she tried on Cruella, it was all over. The depth of the red made her blue eyes look even bluer and her fair skin look like freaking porcelain. When you find that magical lipstick, you just KNOW. And this was totally Helena’s magical colour.
Seriously, how great is this?
We returned to Brooklyn, victorious and happy, and so of course we took photos to commemorate the occasion.
I asked Helena if she had learned anything from this experience that she’d be willing to share with other redheads looking for their perfect red lipsticks. She said, "Don't let anyone tell you that you can't wear certain colours! Be sure you wear some makeup, because lipstick can look weird on bare faces, try EVERY COLOUR on your face--not just your hand--and listen to Alle if she tells you something will look good, because she is right."
I never get sick of hearing that I'm right, guys. And I'd like to thank Helena for sharing her story with me and posing like a champion for all these pictures! Truly she is the best.
What are your best red lipstick-hunting tips, or have you never been? What are your magical reds?