I adore lipstick. If you were here, I’d show you my 60-plus tubes of the stuff, along with over 50 shades separated into three compartmentalized plastic containers in my makeup-kit for my professional work.

In my handbag, there are at least nine or ten different tubes of color at all times, which can be a challenge when trying to find my shade to reapply while driving. (Yes, that’s me swerving over the line on the freeway.)

When Covid hit, and masks were required, my penchant for lipstick came to a sad stall. As you are probably aware, lipstick and masks are not friends. Countless times I have applied lipstick, put on my mask, and smudged color around my face and all over the inside of the mask. Oh, joy.

After having had a massive middle-aged-diva temper tantrum, I figured out how to prevent the inevitable messy mask dilemma with a few makeup tricks.

It’s All About Your Eyes

If you are like me and lipstick is your main makeup item, then with a mask, you look, well, cadaverous. This means that you will have to make-up your eyes more and apply lipstick only when needed.

Eye makeup takes a little longer to apply than lipstick but is well worth the energy when you wear a mask. Try waterproof eyeliner like MAC Technakohl in Brown Border in your waterline and between the upper lashes for a more striking appearance.

Beware of using liner underneath your lower lashes if it has a tendency to bleed and make you look like an owl. Because the mask rubs right where your concealer and eye liner sit, you’ll have to either be vigilant about it going south, or don’t put any there at all.

For sure, waterproof liner helps, but if you’re like me, nothing stops the inevitable under eye smudge. The same advice goes for mascara on your lower lashes. Personally, even waterproof mascara bleeds on me, and it’s a pain to remove even with waterproof eye makeup remover.

Goodbye Dewy Concealer and Foundation

Dewy foundations and concealers are a must-have for older women. That being said, dewy anything attaches itself to a face mask like white cat hair to a black sweater. However, the matte look that was so popular in the 90s doesn’t suit mature skin as it looks heavy and can sink into fine lines and wrinkles.

What’s the solution?

If I’m not doing anything too important that day, I’ll just wear a little concealer and add translucent powder on top to set it and leave out foundation. This is tricky, though. Powder can set in lines and age your eye area – not a fun idea.

Choose a quality powder so that this doesn’t happen – or happens much less. Try Diorskin Nude Air loose powder. Apply with a soft powder brush, lightly dusted on top of concealer and foundation, if you wear it, to make it more immobilized.

I do not recommend using a Beauty Blender sponge to set powder unless you have oily skin. If you get oily throughout the day, touch up with MAC Blot Powder, a wonderful oil absorbing powder that doesn’t build up on the skin.

Primers and Setting Sprays

Another wonderful trick is to use a setting spray on top of makeup or blend with foundation to keep it from moving. This can be done after you apply foundation, or you can mist the setting spray on top of the foundation brush and then apply to hydrated skin.

This has the wonderful effect of holding your product in place all day with little to no residue on the mask. It’s an added step, but worth it if you need to look polished. Try Lancome, Fix It Forget It Hydrating Makeup Setting Spray.

Using a facial primer is another sure-fire method to keep your makeup in one spot. Be sure the product you use is for a matte look – not luminescent as that can add a dewy texture. Try Laura Mercier Pure Canvas Primer Blurring either before you apply makeup, or mix with your foundation and then apply using a brush.

Matte Lipstick, Anyone?

Needless to say, lip-gloss is off the table when it comes to masks. We lipstick lovers must turn to matte lipsticks to get our fix in these mask wearing times. To be sure, not all matte lipsticks turn your lips to chalk and most should be worn with some form of lip hydration.

Liquid matte lipsticks have the benefit of staying put for hours, and therefore not smearing all over your facial mask. My favorite matte liquid lipstick is Chanel Rouge Allure Ink Fusion. The colors are brilliant, and it lasts longer than your husband.

If you dislike matte lipsticks, you can also use your regular lipstick and add powder on top of it to make it less creamy. I use this system for my wedding clients: powder lips to make them dry, then fill in lips with lipliner, apply lipstick on top, then more powder, lipstick, then powder again. Trust me, that stuff’s not moving.

Whatever you decide to do to look pretty and un-smudged in these mask-wearing days, my encouragement is to be inspired. May your glass be half full, and your handbag full of lipsticks. Just keep your eyes on the road.

How do you manage to wear makeup under your mask? Have you become good friends with the smudge? What lipstick techniques do you use to make the stuff stay where it’s supposed to? Please share your woes and tips below!

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