Should I wear makeup?

I don’t wear makeup currently, and I’m starting to wonder if I should.

I didn’t start wearing makeup along with the rest of my friends because I didn’t want to buy non-vegan makeup. If it had mattered enough to me in high school, I would have found vegan makeup, but it didn’t. I didn’t have acne then, so I had nothing to hide. I had my morning routine down to 20 minutes, and I didn’t want to lengthen it. Most of all, though, I liked the simplicity of being barefaced. It broke my heart as child to see my mom panicking when we were running late and she had to put on makeup in the car at red lights. I thought she was the most beautiful person in the world, and I wished I could convince her that she didn’t make herself beautiful by applying cosmetics.

Not wearing makeup was just one of many exercises in mortification that used to obsess me. I once had a policy of never untagging myself from facebook photos, no matter how unflattering. I drew ugly self-portraits. It wasn’t that I didn’t like the way I looked– it was that I wanted to ensure I didn’t get uppity and want to look better. Freedom, I felt, came from never wanting more than you could have. (An irrational part of me also believed that I would be rewarded for this virtuous attitude with random fortune. I was cultivating true beauty through self-denial, after all.)

But now I’m 25 and sorely lacking in beauty skills. I have a basic set of vegan cosmetics (from ELF; it’s both vegan and affordable!), but any time I experiment with it, I think I look like a clown. I wasn’t crazy about the professionally done makeup at my wedding, either. I think it made my eyes look smaller. (Side note: I also wasn’t crazy about my hair. If I had known more about doing hair and makeup, this probably could been avoided). I think I look better in the barefaced photo on the right than I do gussied up for my wedding on left:

Does it just look silly to me because I’m used to my normal face? Would I get used to my new appearance over years of wearing make-up and gasp at the bare face underneath? I like that same wedding portrait a lot more in black and white. Does this mean that the makeup was bad because I only had a few colors to provide the stylist? Or is the B&W just higher contrast?

The real question here is strategy. I like the way I look now, but I’m not getting any younger, and I may want to wear makeup sometimes in the future. This  will entail an awkward phase of experimentation that’s most excusable in teenagers. It’s too late for that, but looking like a kid who got into Mommy’s makeup bag is probably easier to pull off in your 20s than your 30s.

I like the freedom of not being expected to wear make-up. Most days I just roll out of bed, wash my face, brush my teeth, and I’m ready to go. A lot of women give that up when they start thinking of their make-up regime as “putting on their face.” I swore as a child in my car seat watching my mom frantically apply mascara in traffic that I would never give up the prerogative to show up bare-faced. But I’m afraid my stance has robbed me of the power to show up a little prettier, or a little less concerned about the state of my acne. There are days when I waste far more time with unproductive worry about zits than I would have applying makeup. Am I free when I don’t really have a choice?

In the spirit of Critch‘s Axiom of Choice (hat tip Ruby Bloom), I am planning to learn this great feminine art form so that I have the power to make a meaningful choice. At the very least, it promises to be a fun diversion. Tips from make-up veterans would be welcome.

Having resolved to learn the ways of make-up, I am left the ponder the other reasons I have avoided the lipstick tube and compact for so long. I suspect I have been applying ace-in-the-hole reasoning. Never really trying to look better left me with the comforting fantasy that I would look amazing if I put in the effort. I have rejected this reasoning almost everywhere else in my life– professionally, in dealing with my mental health— so why would I continue to uphold it here? What matters is results, and if I want to look beautiful, why not go for broke sometimes? I think the good just won another small battle against the perfect in my mind.