From Marilyn Monroe to Lupita Nyong'o, Hollywood glamour has always been about that unforgettable red lip. That look is so much more than just a lip color. Rocking red lipstick sends the message that you're the kind of badass woman who is completely unafraid to go bold. Or, okay, maybe you're experimenting with that image! Either way, it's a look we should all feel comfortable trying. We owe it to ourselves!
Of course, one of the reasons red lipstick is considered so brave is that it can be tough to find the right product, get it to go on smoothly, and have it stay put. (Maybe because it's just so in-your-face, red lipstick seems to have a way of getting all over your face!)
Thankfully, beauty experts are happy to share their tricks for pulling off that iconic red lip.
Exfoliate your pout.

Prepping your lips for lipstick (or gloss or stain) application is key when you're wearing any color, but particularly when you're intent on rocking red. "Exfoliation will help with uneven tone, dry skin, and fine lines that become emphasized with bold red tones," explains Cashmere Nicole, makeup artist and the CEO of cosmetics line Beauty Bakerie.
You can buy a lip scrub like Tarte's Maracuja Lip Exfoliant, made with raw sugar and a balm packed with antioxidants, or make your own DIY scrub. Hillary Kline, a freelance makeup artist from Minneapolis, shares her own personal "recipe": "Take honey and sugar, and mix that together and then take a toothbrush and apply it to your lips. Let it sit for a little bit and then scrub, getting rid of any dead skin particles. Top with a lip balm or Vasoline for extra moisture."
Tarte Maracuja Lip Exfoliant, $16; Sephora
Treat your lips at night too.

If your lips are really dry (unfortunately, not an uncommon side effect of winter!), give them a little extra love with a nighttime treatment. Alejandro Falcon, the artistic director for Osmosis Colour Cosmetics and a celebrity makeup artist who's worked with Jennifer Lopez and Christy Turlington, likes Osmosis' Skincare Refresh PM Eye Serum. "It will not only condition and hydrate the eyes but the lips as well," Falcon says. "If it can restore a healthy barrier and plump fine lines around the eyes, why not for your lips too? Just use a small amount before bedtime and awaken with soft smooth lips."
Osmosis Skincare Refresh PM Eye Serum, $68; Dermstore
Prep and prime.

Once you're ready to apply your favorite shade, consider priming your lips with a product like CoverFX Pressed Mineral Foundation. "Pressed base mineral foundations used as a primer can prevent lipsticks from bleeding," explains Falcon. "Apply a small amount gently to just slightly erase the lips." The minerals act like a "base coat" for your lip color, preventing it from budging.
CoverFX Pressed Mineral Foundation, $36; Sephora
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Choose the right liner for the look you're after.

You may have seen or heard of clear/invisible liner (like Sephora Collection Beauty Amplifier Universal Lip Liner), which works with any color lipstick as a barrier to prevent feathering, explains Derek Selby, a makeup artist and global ambassador for Cover FX. But if you want a more defined or voluminous-looking pout, go with a regular liner that matches your lip color.
Another liner tip: "If your red lipstick or liquid lipstick is very saturated with color, I like to line the lips after," Selby shares. "This is easier to do and allows you to get a very precise line to the lips. If you are wearing something more sheer or a lipstick formula that isn't long-wearing, I like to line the lips first and fill in the lips with the lipliner for longer wear." (If you're using an invisible liner, you'll obviously want to line first, as well.)
Sephora Collection Beauty Amplifier Universal Lip Liner, $10; Sephora
If you're a beginner, give yourself a break.

If you're a red lip novice, you can work your way up to using that super-bold lipstick that's more than a little intimidating to wield. "If you are just starting out as a red lip lover, start with a gloss or a stain, then work your way towards a bold matte or bright cream," Falcon advises. One of the most beloved stains is Benefit Cosmetics's Benetint, which can be used on your cheeks, too!
Benefit Cosmetics Benetint, $30; Benefit Cosmetics
Consider how much staying power you want.

If you're not such a beginner, and you're debating what formula to go with, consider how long you want your red lip to last. "Classic lipsticks are the pigmented creams you find in a tube or pot, and offer lots of instant bold color but wear off quickly," Nicole says. "When you're going out for a drink and just need an instant boost of color, a classic lipstick may do the trick. But when you're planning an evening out, or you want to ensure your lip color lasts through every part of your busy day, a matte lipstick will provide the long-lasting color you need!" One of the most beloved matte reds is MAC Cosmetics's Ruby Woo, which has a blue undertone, but is considered universally flattering.
MAC Ruby Woo, $17, MAC Cosmetics
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Figure out what undertone suits you best.

"Red lipstick with a slight orange undertone usually looks great on light skin tones and light hair color," explains Falcon. "It is not overwhelming, and it adds just the right amount of warmth."
If you have a darker skin tone and darker hair, try a red hue with a bluer undertone. "This provides enough intensity for the darker tones on the face," he says. "You can easily hold your red lipstick against a cool or warm background, like a blue scarf or orange sweater, to see if it either complements or clashes. If it complements, then it is cool. If it clashes, it is warm."
If your red doesn't look orange or blue, then it's neutral, points out Selby, who notes, "Everyone looks great in a neutral red, but my favorite is a blue-red that makes your teeth look bright white!"
For foolproof application, go with a creamy formula.

If you want a red you can throw on quickly without a lot of fuss, or you just want a formula that's more forgiving in its application, go with a creamy one, like Urban Decay Vice Lipstick in Rock Steady. "The most user-friendly formula is a creamy texture," confirms Selby.
Urban Decay Vice Lipstick in Rock Steady, $17; Urban Decay
Tone it down or play it up.

Once you've settled on the color that speaks to you, manipulate it with a gloss if you want to tone it down, says Falcon. Selby agrees: If you want to make the color more matte, use a setting powder on top, or if you want to amplify shine, top it with clear gloss, he says. One cool trick: "Add Cover FX Custom Enhancer Drops in the center of a red lip to create an ombre effect," Selby shares.
Cover FX Custom Enhancer Drops, $42, Sephora
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Clean it up with a concealer.

Once your lip color is in place, you may still notice a little bit of feathering; you can perfect the look with a bit of concealer. "If you made mistakes or the color is out of line, use concealer and a small concealer brush to go in and clean up the edges," Kline advises. "The idea with the concealer is for it to almost act like an eraser. Make sure you blend the concealer as well."
Clinique Airbrush Concealer, $20.50; Clinique
"Neutralize" the rest of your look.

Of course, certain times and events call for a full face of dynamic makeup, from faux lashes with fun cat-eye liner to smoky shadow and your red lip. But for the most part, a red lip will really pop if you play down the rest of your look. Selby recommends reaching for a soft, natural blush (like Naked Flushed) to avoid that "literal '80s" look. "Dial back the rest of the makeup and let the red lips be the star," he recommends.
Urban Decay Naked Flushed, $34, Urban Decay