How to Highlight Your Favorite Features

I have a big gap between my teeth, and I’m very into it. At 15, when my braces came off, my teeth (which had been forced together in a cage for 2.5 years) sprang apart again during their very first night of freedom, as if to cry, “You can’t contain my spirit!” The orthodontist sighed and told me she could fix the gap if we put the braces back on, but I refused. The gap, I thought, looked cool. Years later, it has become my favorite feature. It defines my smile—and I make sure to highlight it as much as I can. When I whiten my teeth and put on some ultra-bright, blue-based red lipstick, I might as well be wearing a sign that says, “Hi, look at my mouth.”

Now think about your favorite thing about your face. Is it your pouty lips? Your big, soulful eyes? Maybe it’s the dainty smattering of freckles on your nose, your defined eyebrows, or the fact that you never break out (if you have all of these things, don’t talk to me). Whatever your favorite feature is, the easiest way to play it up is with makeup. A few simple tricks can draw someone’s eye right where you want it to go.

To really play up your best features, David Klasfeld, the founder, CEO, and creative director of Obsessive Compulsive Cosmetics says you first have to think outside the box. “Many people have one feature that they’re more comfortable playing up than anything else, but I would challenge those people to experiment and focus on features they don’t usually consider. The results can be surprising,” he says. Very diplomatic, David. Challenge accepted. Here, his hints for adding drama to different areas of the face.

Eyes: layer similar shadows in different textures

How do we get “look into the depths of my soul” eyes? “It isn’t always about packing as many different colors on to the lid as you can,” says Klasfeld. “Some of the boldest eye makeup looks can also be the simplest monochromatic, one-color statements.” One of Klasfeld’s favorite techniques involves layering a loose pigment color over a coordinating cream color “to not only create depth of color but to ensure longevity.” One combo we love: OCC Loose Colour Concentrate in Static over Anna Sui Cream Eye Shadow in 250 Metallic Purple.

Lips: conceal around the lips for crisp application

Sometimes, you just want your lip color to...KABOOM. “To really make lips pop, liner is an absolute necessity, whether you’re working with a matching or contrasting color,” says Klasfeld. Prep is also crucial. “Beyond products like lip primer and anti-feathering pencils to prevent bleeding, it’s always a good idea to use concealer around the lips to make sure the application looks crisp.” OCC Lip Tars—universally loved for both the insanely high pigment level and color selection—are a safe bet when you want to go “big.” A few of Klasfeld’s favorite shades: NSFW, “a truly balanced red. I have yet to find someone who doesn’t look fantastic in it,” and, on the bolder end of the spectrum, RX and Traffic. “Even slightly ‘out there’ shades like the latter two, when applied precisely and worn with confidence, can be real show-stoppers,” he says. (Inglot Cosmetics AMC Cream Concealer is excellent for cleaning up edges.)

Skin: lighten up and use a good brush

How I wish that my skin was my best feature. If you’re blessed with flawless skin and want to play it up, Klasfeld says to play it down. “When it comes to skin, less truly is more. Nobody wants to be perceived as wearing dramatic foundation. Most people can get away with less coverage than they think they need on a daily basis. Cell phone cameras capture so much detail now, and heavy foundation will always look just like heavy foundation,” he explains. When doing your base, use a good foundation brush (try the OCC #002 or the Cover FX Liquid Foundation Brush) and a light hand.

Bone structure: try highlighting and contouring

What about your bone structure? Can really good cheekbones or a sculpted jawline be the feature you play up? Klasfeld was emphatically in the YES camp. “Absolutely! Highlighting and contouring can be achieved in simple wearable ways,” he says. And it doesn’t take anything more than what you probably already have in your bag—a good neutral blush and versatile highlighter, or two concealer shades, one lighter than your skin tone and one darker. “Buff them onto the high and low planes of the cheek, respectively. It’s a makeup artist trick accessible to the everyday wearer,” explains Klasfeld. To learn more about contouring basics, read this and this.  

And no matter what: be confident

At some point, my mother told me that if you were planning to play up a feature on your face, the rest of your makeup should be quiet (i.e. the old maxim “either eyes or lips, but not both”). When I asked Klasfeld if he follows that rule, he said, “Absolutely not! It all comes down to your personal style and comfort zone. If you can wear a dramatic eye and a bold lip together and feel confident doing so, that is all it takes. Confidence is what makes or breaks the application.”

And there is the lesson: if you’ve got it, flaunt it. And, most of all, play up your confidence—that’s the real best feature there is.