4 Ways to Overcome Your Fear of Wearing Bold Lipstick


All my life, I’ve loved lipstick. Preferably red, preferably matte as hell, preferably expensive and velvety. My mom showed me how to put it on properly when I was 13 years old, and since then, not a week has gone by where I haven’t creeped into the bathroom and put on some really bright shade, just to see how it completely changes my face. I have, literally, boxes full of lippies, separated by color. There’s a “pinks” box, a “reds” box, a box full of glosses and liquid tubes, and an “I’m sure I’ll need orange and purple at some point” box. 

But until recently, you’d never have known it. For a long time, I never wore lipstick outside my house. Never. The most I would do was a bright stain for serious makeup occasions like New Year’s Eve. The really chic, glamorous shades stayed at home, with me, where I’d try them on only to sashay around my house. I was too shy to go bright out in public. I felt like, on me, those colors were “too much.” Like everyone would think I was trying too hard. When you put serious lipstick on, it’s like a beam of light aimed directly at your mouth, and I wasn’t ready for that kind of attention, especially not on the train, or at my job! Who was I trying to impress, anyway?

Then, last year, as I was painstakingly layering different shades of OCC Lip Tar in my bathroom late one night, it suddenly hit me: you know who I should be trying to impress? Myself, dammit. My habit of not wearing lipstick out in public, either at work or when going out, when I actually look great in lipstick, was a symbol of something scarier for me: I didn’t want to draw attention to myself...ever.

There’s nothing wrong with getting a little attention, for wanting to look great for yourself or others. I set out to change my attitude pronto. And I’m happy to report that, a year after I had my come-to-Jesus moment in front of the mirror, I have zero problems wearing my brightest, most obnoxious lipsticks out in the world. I even ran out of one, and for the first time, had to replace it. It’s like: LOOK AT MY MOUTH, Y’ALL. I put this on for me, but you can look, too, and what’s more: I want you to look at me.

Are you like me? I know this is a beauty site, so I might be the total weirdo here. But if you’ve ever felt a little too shy, or not quite confident enough to rock some seriously visible makeup, you can get over your fear, too. All you need to do is:

1. Pick a patron makeup saint

You need guidance from a higher power! My patron makeup saint is Mimi from the Drew Carey Show, which I used to watch as a kid. She wears whatever she likes and doesn’t care what anyone else thinks. Brilliant colors? Bring it on. Insane eye shadow? LET’S DO THIS. Your patron makeup saint could be anyone who radiates confidence and makeup artistry, from Jessica Rabbit to Effie Trinket to RuPaul. When you feel nervous about wearing a bright color, think to yourself, “Would RuPaul bat an eyelash over neon pink lipstick? I THINK NOT.” Then sashay away into the world.

2. Practice at home

Wish you could wear a shiny, scarlet red lip to work? Give it a trial run at home a few times before taking your act on the road! And you’re not alone in this. There’s lipstick advice everywhere (ahem!). You can read all about how to get the perfect red or the ideal matte orange, or whatever you want. I highly suggest doing some homework. (Currently the best technique I’ve seen is to apply red lip stain BEFORE you apply red lipstick—try it, it’s amazing).

3. Take baby steps

Wear your neon coral lipstick to, say, the supermarket. GASP. If no one faints from shock, try wearing it on the bus. I know. You might feel silly, as if everyone is staring at you, but trust: everyone has seen far more shocking things on the bus than a confident person rocking an almost-glow-in-the-dark lip.

4. Just do it!

Bring your “crazy” makeup to work, and into your life! When you first start wearing bright colors at work, act casual—kind of an “oh, this old thing?” scenario. You can always wipe off your color in the bathroom if you must. But why would you? You look confident, great, and so colorful! Have fun!