Pretty Woman: A Modern Approach

Pineapple Skies.
Kenosha, WI. 2020.

One year, 3,000+ readers, 8,000+ blog views, and half a global pandemic later; I’m pushing myself even harder to stay creative, graceful, and vulnerable. What first began as an outlet for me to find and harness my voice; morphed into a mission to offer confidence and support to those still growing (and laughing) through their pain.

As we continue on our respective journeys, it is important to remember that no one considers your imperfections as frequently, or intensely, as you do. If you’re lucky, most of the people you know don’t quite care what you do or don’t accomplish (or the way in which you do it). There is only a small population of people that act as both judge and jury, feeling the need to label and diminish your radiant light. As Brene Brown would say to those who are not playing in the arena of vulnerability: your feedback isn’t welcome and you may kindly f*ck off now 🙂

Self-Esteem, Confidence & Sex Appeal
Self-esteem is a tricky b*tch. Tied closely to identity, ebbs and flows in confidence, and inward projections of virtue; it serves as the meter reader on your internal operating system. It can be temporarily bolstered in moments of high confidence; typically in familiar situations and via external measures (ie: awards, promotions).

Self-esteem can be vested in virtually any principle at varying depths and intensities: relying heavily on success at work, the approval of friends, esteem-able acts, etc. Confidence subsequently works to establish trust in the self and endorse future tenacity.

Real confidence can be spotted quicker than Joe Exotic can say “Carol F*cking Baskin”. It immediately presents itself as improved posture, sustained eye contact, and conversational reciprocity. It is later revealed through emotional vulnerability, relational stability, and low reactivity. Steamy, I know.

Confidence then feeds the development of sex appeal by encouraging expressions of creativity, intimacy, and the boldness to exchange latent desires. If you’ve seen that gaze, you know.

These mechanisms work together to establish attraction; making appearances themselves nearly obsolete. Even so, most humans require intermittent affirmation of their desirability by their partners. This does not necessarily denote underlying insecurity or narcissism; but rather a healthy need for reinforcement of shared attraction.

I still remember the first time I overheard “oh, I didn’t know Katie was hot“. Call it dramatic, but this blunt observation invited a cascade of changes in my life in the following years. I found myself being drawn to men that didn’t compliment me, with the excuse that they figured I didn’t need it. It began to feel like asking anything more would be either too indulgent on my part, or altogether insincere on theirs.

Somewhere along the way, I since decided to stop ‘playing small’. I decided to stop asking for less than I wanted. I stopped feigning coy. I reclaimed my space. As someone who is generous with adventure, affection, and applause; I’d like the same in return (and without provocation).

Confidence, Cosmetics, & History
Humans have used cosmetics to enhance their physical appearances for thousands of years. Dating back as far as Ancient Egypt and Ancient Greece; we’ve obsessed over freshening our breath, altering the color of our skin, and drawing attention to our eyes. Egyptians even took special care to apply make-up to the dead, in hopes that they’d remain desirable in the afterlife.

Applying kohl to line the eyes, fill the lids, or extend the lashes was a two-fold benefit; welcoming intrigue and concealing identity. If that doesn’t sound like the perfect Saturday night, I don’t know what does.

As rare pigments became available to high society, cosmetics also served to distinguish social classes. While modern culture maintains a harsh prejudice against blue eye shadow as rather ‘trashy’, it was once an indicator of unmatched wealth. (Click here to listen to an impossibly cool Stuff You Should Know podcast on the much coveted Indigo pigment!)

From the end of the Renaissance to the early 1900s, most cosmetics were employed by prostitutes and stage workers alike. Yet, as ingredients became more regulated (and less toxic), marketing began to creatively entice usage by the everyday woman.

During wartime, cosmetic companies began to encourage women to emulate Hollywood glamour; as a show of freedom and unmatched patriotism. Not only was this intended to please those on military leave, it was to offend Hitler himself. This was because he outlawed red lipstick and nail polish during his tours of oppression. And just for that, I’ll now be sure to swipe on some rouge every. single. day. (This also makes Shosanna’s warrior-esque make-up application scene in Inglourious Basterds that much more bad*ss!)

Each decade since has seen a new cosmetic trend related to an underlying social movement. It wasn’t until the 1970s, however, where marketing gurus invented the concept of ‘daytime’ (natural) vs. ‘nighttime’ (smoky) looks.

This prescription for ‘appropriate’ appearances indirectly endorsed specific behaviors and characteristics for females based on time of day and so, their expected audience. For example; stay mild, meek, & pure in daylight, yet inspire intrigue, mystery, & fantasy after sunset. Or, as Ludacris might explain, be a “lady in the streets and a freak in the sheets”. Honestly, why are men in charge?

Beauty & Womanhood
While being initiated into womanhood, it’s almost as if we’re told to pick two: beauty, intelligence, or sexual prowess. While I have the pleasure of knowing many women that possess all three attributes, the historical lens of women’s utility does not allow all to be true at once. I believe each woman has the capacity for all three; and thoroughly enjoy men’s reactions when they recognize this.

Consider Pretty Woman, the tale of a fallen female prostitute saved by the riches of a geriatric patron (not quite, but close). Gorgeous as hell and well versed in promiscuity, she’s dangerously approaching that forbidden triangle of female attributes. So, the writers paint her as half-witted. She literally delivers a line that she liked the opera so much, she ‘almost peed her pants’. Woof.

Thanks to Kylie Jenner, Youtube, and Instagram the cosmetic industry is more accessible than ever. Many women have the tools to completely transform their appearance within the comfort of their own home. Every day offers a new opportunity to celebrate, express, and experiment with our unique features. Each day, we get to decide who we want to be.

History is quick to influence our options: are you a Cleopatra or Hypatia? Marilyn or Jackie? Harley Quinn or Poison Ivy? Veronica or Betty? In other words, are you sexy & unstable OR reasonably beautiful & relatively mild mannered? Take your pick. (Insert two relevant G-Eazy song recommendations: one for Marilyn & one for Harley.)

A recent Instagram poll revealed 60% of my followers prefer ‘natural’ looks. However, free responses indicated that make-up is regularly used as a vehicle for creativity and confidence. This conflicting data, and the fact that most men think Kardashian beauty is natural, leads me to believe women should just do whatever the f*ck they want with their own faces.

One thing is for certain. Men love bare-faced selfies. Maybe it’s the notion that your guard is down, an affirmation that they’re your first thought in the morning, or that they get access to a precious side of you. Surprise your mans and treat him to an extra hit of your love & light!

My Own Take
My beautiful friend Kelly recommended this blog topic. She asked that I review my experience with beauty rituals and it’s impact on my life (career, relationships, self-esteem, etc).

Growing up, I was the quintessential tomboy. I’d leave our apartment in the morning and come back at dusk, coated in dirt and sand. For my fellow Now & Then stans, I identified with Roberta. Unless you were Devon Sawa (fingers crossed), I knew I wasn’t an object of attraction.

My sister is 5 years older and wiser, and grew very interested in make-up early on. Employing Kevin Aucoin’s Face Forward tricks, she’d transform my mother and I into total masterpieces.

As the years passed, my own affinity for the arts continued to grow. I became obsessed with the history of luxury fashion shows, creating edgy collages, and tossing glitter at my face. I began to idolize old Hollywood drama, Parisian style, and advertising culture altogether.

It wasn’t until college that I grew sick of being a freckled cutie. While I treasured my intelligence, kind heart, and sense of humor; I didn’t feel fully actualized or understood. I hadn’t harnessed my grown-ass-woman energy just yet. I was swinging for Gosling’s “perfect combination of sexy and cute”, with a little more 2000s R&B music involved.

I can think of a few pivotal moments that helped me grow closer to this actualized self. Joining a sorority of undeniably bad*ss women, traveling alone, experiencing new relationships, spearheading career developments, relishing in true love, and hella tattoos. But, that was not without equal amounts of pain and strife.

Esther Perel, world-renowned psychologist, argues that failed relationships are often a sign that one has outgrown themselves (and not necessarily the other person). In Western culture, relationships are often tied so closely to our own identities and projected futures that this simple truth can be overlooked. Knowing this would have helped me settle into myself more gracefully in the last decade, helping allow my partners do the same.

While I can’t say my morning KatVonD ritual (the makeup brand, not the vampire sh*t) has a direct impact on my work or my romantic relationships, I can say it’s certainly not hurting. I find that not looking 12 years old is a positive thing in both cases.

I take pride in my unapologetic lust for life. I’m vulnerable, warm, understanding, adventurous, quick-witted, and passionate. But, much like my daily smoky-eye, I’m not without flaw. I’m a little bold, a little loud, a little intense. But, I mean well.

I’m striving for F. Scott Fitzgerald’s hauntingly beautiful, “no, she wasn’t beautiful for something as temporary as her looks. She was beautiful, deep down to her soul”. I want to make a lasting impact on those I’ve known and loved, and I won’t stop trying.


P.S. Click here for the latest bad b*tch playlist. It’s perfect for getting ready (to hang out in your living room)!


“To love someone long term is to attend a thousand funerals of the people they used to be. The people they’re too exhausted to be any longer. The people they don’t recognize in themselves anymore. The people they grew out of, the people they never ended up growing into.”

Heidi Priebe