My Mother has never worn makeup. The only exception being the occasional wedding when she will attempt the lightest touch of blush and powder that is nearly indistinguishable from her usual appearance. Fittingly, I believe it was my eldest cousin’s wedding that led my mother to agree I could wear makeup for the first time. I was in middle school, and in the wedding party as a junior bridesmaid. We made a trip to the mall to go to the Clinique counter and had the consultant do my makeup. We left with a bag full of natural look makeup, nearly indistinguishable from my usual appearance.

My makeup routine didn’t change much for twenty years. My signature lipstick – Smashbox Be Legendary Lipstick in Nylon Nude – was basically the only lipstick I owned up until three months ago. It works well with bronze blush and shades of taupe eye shadow. The words natural, neutral, and nude appear a lot in my make up collection, which fit in a tray in a single drawer of my bathroom vanity. It’s all very good for creating a fresh face that does not attract undue attention.

I wouldn’t have expected Halloween to be the catalyst for change. Costumes and accompanying make-up always seemed a lot of pressure. It was really the love of The Rocky Horror Picture Show and the decision to go to a midnight show that started it all. You simply cannot go to a midnight picture show on Halloween weekend and not dress up so I settled on Columbia and went all in. The month of October was filled with makeup video tutorials, weekly trips to Ulta, test runs, and no less than half a dozen not quite right red lipsticks. The winner was Maybelline Vivid Matte Liquid in Rebel Red. It’s a strange feeling to look in the mirror and see yourself in vibrant color for the first time. I saw a rebel. I saw a confident and beautiful woman, unrecognizable but at the same time me. I felt more myself than ever; or maybe it was the pieces of me I wish were louder that were given voice with a touch of Rebel Red.

Last month, I decided on a pixie cut – I’ve always been more adventurous with my hair than anything else, but this is by far the shortest it has ever been. Now I look in the mirror and without makeup I see my brother. If I choose Rebel Red my paternal grandmother is looking back at me – I now share her short, dark hair and she was never without her red lipstick. Maybe Nylon Nude is still the most recognizable as me, but I’m enjoying trying on different shades. Since I’ve met Rebel Red, the lipstick collection is continuously expanding with bold new additions. I was out gallivanting in NYC with a close friend and surprised myself by admitting I wanted a purple lipstick. A Sephora magically appeared before us – Ayesha (Kat Von D Everlasting Liquid Lipstick) was clearly meant to be mine.

There’s still a not so quiet voice in my head that questions whether I can really pull off colorful choices (aren’t I too old for such silliness after all). The more I try new things the easier it is to ignore the doubts and go bold. I still love my Nylon Nude and use it more than any other lipstick but am learning not to take myself so seriously; a new shade of lipstick is a tiny push outside my comfort zone.

Some might say people hide behind makeup but I would argue makeup is a silent expression of self. I am awkward and confident. I am quiet and outspoken. I wish to be invisible but yearn to be seen. Lipstick is a flirt. A hint as to how I’m feeling on any given day. Do I want to blend in with the world as I traverse the crowds of commuters or garner a second glance (I’ve never really considered myself a head turn kind of girl). Don’t be fooled, the days I feel most awkward and desire nothing more than invisibility are often the ones that require Ayesha for a push of fierceness. Is that hiding? I would say no, it’s surviving.