How To Create the Perfect Winged Eyeliner Look + Floating Eyeliner at Critics Choice Awards

Simply follow these professional makeup artist tips and product suggestions for your most wow-worthy wings.

Are you ready to earn your wings? Well, grab your liquid liner, take a deep breath, steady your hand, and channel your inner Dita Von Teese; this article is chock full of tips and product suggestions for executing the perfect winged look!

There’s nothing like learning (or perfecting) a new makeup skill.  And given winged eyeliner is a sultry look that never goes out of style, we’re setting our sights on this enduring trend.

A Hollywood Classic

We have all seen winged eyeliner executed to perfection in magazines, on the runway and gracing the lashlines of many celebs’ perfect lids as they waltz the red carpet. Think Angelina Jolie, Dita Von Deese and Adele; all these ladies rocked a winged look with perceptibly zero effort and maximum impact. Even though it was her amazing pipes that made her a household name in the early 2000’s, most cannot think of Amy Winehouse without picturing the aggressive sweep of kohl that graced the female crooner beauty’s eyes and complemented her extreme beehive hairdo.

The latest twist on winged eyeliner was spotted at the Critics Choice Awards - Peyton List turned heads with her floating eyeliner. And Elle Fanning paired her classic winged eyeliner with bold red lips, while Issa Rae and Selena Gomez also rocked the red carpet trend. 

And more recently, actress Julia Fox, who made headlines for her brief romance with Ye, has been rocking highly exaggerated, graphic winged eyeliner – think Natalie Portman’s iconic  look in Black Swan.

Whichever style you choose, it is a look that takes patience, calm, and dedication, and this year I am setting an intention to snag the skills to get the perfect swoop; I suggest you join me! I reached out to a couple of my favorite makeup artists who have mastered the art of the vintage vixen look, complete with perfectly executed cat eye; so, let’s get into it!

You Do You, Boo

The Cherry Dollface, aka Cherokee Jackson, was living the dream of the late 90’s/early 2000’s in Portland, doing pin-up modeling when she started realizing that many makeup artists in the area were not well versed in vintage makeup looks. So, what was a rockabilly girl to do? She hit the books and got to studying, learning how to style herself (including makeup and hair) for shoots.

When people started asking about looks and application, she shared her skills with the interwebs by starting a YouTube channel devoted to vintage and retro makeup and hair styling. Her following proceeded to explode and now, a decade after debuting her YouTube platform, she has over 300,000 subscribers and an Instagram following of close to 200K.

Cherokee (who is also a published author)also travels the world, teaching classes and styling shoots herself, all while operating a permanent makeup business as well; this beautiful dame is rocking some serious girl boss goals. When I asked Cherokee about liner looks and how we know which one is right for each person, she expressed that it is all about experimentation, and killing the look you like. “I don’t really prescribe to the ‘do blank for your face or body shape’ mentality,” she says.

In other words, if you like it, DO IT.  “For example, for those who have small or hooded eyes, a giant winged liner will make your eyes look smaller and will also be an aggressive look; but if you love it, who cares! I love when people experiment,” she adds.

It’s Prime Time Baby

As a master makeup artist, Ali Rose of the Ali Rose Beauty Team knows that any makeup related work of art needs a clean canvas; that means primer is integral. Primer helps to lock in your work and extend the life of the artistry you have created on your luscious lids.

Ali’s favorites are Tarte’s Base Tape Hydrating Primer, as well as every influencer’s fave, P. Louise’s Eye Base; both create a smooth, matte finish and provide the perfect foundation for Ali’s next pro tip. “Build the look with a base of well-pigmented shadows, either natural toned or dramatic. Just make sure the shadows are saturated with color. My favorite palettes to use for a dramatic winged eye look are from Natasha Denona,” she says. Once you build your eye’s color story, that is when this eyeliner look gets real.

Execution is All in the Wrist

Technique for applying a winged eyeliner look is like a fingerprint; everyone has one, and they are all different. Cherokee states that “a lot of artists will start the liner from the inner corner of the eye, stop halfway and then pull the outer wing in to meet it in the center in one fell swoop. However, I teach beginners to start in the inner corner and make short strokes outward until you hit the end of where you want your wing to be. I also keep my line above the lashes because the lashes will mess you up and make your strokes wobbly; it is easier to fill in under that line once it is perfected.”

Another way to create a clean line is to lay the side of your liner tip against the lash line intermittently, creating a “map” of sorts, connecting the dots, and creating a clean baseline for a knockout wing. Not sure of where to place or create your wing? Ali suggests utilizing a sticky solution. “Eye tapes can be easily applied and help to give you a clean line; if you make a mistake with your winged liner, cleaning up with concealer and pointed cotton applicators is a snap!”

Get the Tools of the Trade

So, you have perfected your technique and application, but you want to utilize products that will extend the life of your look? We got you, kitten. “I like to use waterproof liner on my inner corners because allergies make my liner smudge, but I don’t love the way most waterproof felt liners draw a wing, so I use a regular liquid liner for the rest of my line. This is how I get the sharpest wing! I absolutely love Benefit Roller Liner Eyeliner for the inner corners and The Balm Schwing! Liner Eye Liner for the wing.”

Ali also agrees that the right product makes all the difference in executing a clean look, and once again, pigmentation in product is key. “I love using the Kat Von D Beauty Super Pomade Vegan Eyeliner, Shadow and Brow Pigment Gel Liner, paired with the Sigma Beauty Winged Liner Brush; I get crisp application, and the gel is water proof, very deeply pigmented and the product doesn’t dry out fast like other gel liners.”

Ali also incorporates the dynamic duo of liner pencil and pen for a long-lasting look. “I love the Makeup by Mario-Line and Lock It Set; the pencil is waterproof, heavily pigmented, and really easy to work with; the liquid liner has a very fine tip to get a beautifully precise wing.”

Well, it is official…. you have executed the perfect winged eyeliner! Time to set the intention to learn some maquillage magic, and you did not disappoint! But there is one more step…. you gotta lock it up. A winged eyeliner look can be fickle, and the smallest swipe can annihilate your exquisite example of makeup mastery. Ali suggests the cosmetic version of the CTRL+S shortcut - setting spray. “I love Skindinavia-The Makeup Finishing Spray; it’s a great setting spray that is water-resistant and locks in your look for the long term.”

So, there you have it; mission accomplished.  Time to fly!