Tattoos in the Corporate World

Over the past decade or two, the stigma around tattoos has gone from taboo to becoming mainstream. What some people do not know is that during the daytime, I am a manager in the Corporate World who clearly does not fit into that traditional mold. Working for the same company for over 15 years, it has allowed me to see first hand how the stereotypes have slowly started evolving and what it means to be different in this very traditional environment .

The stereotypes of what people “should” look like working in the Corporate World.

When I began working for my employer in 2002, I was a 20 year old College student that had a couple small tattoos and wore fitted clothing (aka booty pants & slinky tops). Looking back now, I seriously cringe at the thought of my younger self but it was a stepping stone to developing my confidence and discovering how to refine my own personal style. At that time, it was necessary to cover your tattoos if they were larger (aka not a little ankle tattoo) or have them in places that didn’t attract any attention. I remember asking my manager what the Corporate policy was on tattoos and they just said it was frowned upon so make sure to not cause any attention to the matter.

Many people are forced to live two lives: work vs their true selves.

As the years progressed I slowly started collecting more tattoos, always making sure they were placed in areas that could easily be covered in the workplace. By 2008, I had 6 tattoos that were all still considered small in size but my fascination with the artistry had evolved into a passion. I quickly became immersed into learning more about the different tattooing styles and artists. My love of the art really became a part of who I was but how could I start using my body as a canvas knowing my professional career was taking off? The last thing I wanted was to hinder my opportunities due to the old fashioned stigmas that still existed in the Corporate World.

Tattoos from my earlier years.

In 2010, I met my wonderful husband who admittedly had a thing for women with a tattooed arm sleeve. We both admired the beautiful artwork on other women but I knew it was out of the question for me because of the workplace. This was around the time that I decided I wanted my body to become a canvas to showcase my interests and passions in life. In 2012, when the opportunity of a lifetime of being tattooed by one of the best artists in the industry, we jumped on a train to Chicago to meet Hannah Aitchison for my 30th birthday. The plan was to get a tattoo of a beautiful pinup on my back to commemorate my lifestyle of all things pinup. Apparently Hannah had BIG plans, she had designed a piece that would cover my entire back. It was in that moment that I made a decision that changed my life forever and needless to say, I struggled with a lot of self doubt and feeling of regret in the weeks that followed.

Stephanie Castro pinup by Hannah Aitchison.

When I returned home, I now had to tell my parents who are very traditional about this massive tattoo and more importantly, my boss. They all knew about why we were going to Chicago so it wasn’t like I could hide it for very long. The moment my boss excitedly said “well, can I see it?”, I knew the stigmas might actually be changing thanks to open minded people like him. This opened the lines of communication and we talked regularly about tattoos in the Corporate World but he felt that the individuals in senior leadership still frowned upon them. He cautioned me to keep mine in areas that would not be seen, aka do not get your arms tattooed. That thought stuck with me for years, I shied away from doing it and started using my upper legs as my canvas.

Fluff Susy Sailor by Hannah Aitchison.

By 2013, I had my full back tattooed along with the two front of my upper thighs. When I was out in public, I received endless compliments from strangers and what was often said was “I don’t usually like tattoos, but yours are so nicely done…they are beautiful!” When the little old ladies starting paying me compliments, it was in that moment that I knew the world was changing for the better. I was dressing pinup full time while at work and stopped shying away from covering up my back 100%, which undoubtedly opened the lines of discussion with my coworkers and management. Employees felt more at ease to not cover up and tattoos became the norm, not the exception.

Inspired by my love of vintage by Malibu Budd.

It was not until late 2014 that I finally decided it was time to break the old Corporate mentality…I got my right upper arm sleeve tattooed. I can say this, it was a decision that I struggled with for a very long time even knowing society had changed for the better…would this decision hinder my career advancement? In the end, I felt that what I had chosen had deep emotional meaning to me and it was a risk worth taking at this stage in my life. Still, I knew it could be covered with a cute cardigan when in mixed company. No matter how inclusive people are, I think the deeply ingrained years of tattoos being taboo never truly leave us.

A tribute to my parents by Malibu Budd.

After that life changing decision, I truly believe the years that followed was when we began to see the Corporate World finally adapting with its employees. Eventually I got my left arm tattooed as well as continuing down my legs most recently. Everyone in my workplace doesn’t even blink an eye now that I leave them uncovered regularly and are pretty excited to see when I get new artwork.

Tropical Floral Sleeve by Luis Puedmag.

My love of Disney by Miss Mae LaRoux.

Cover up due to a terrible burn by Malibu Budd.

I know the stereotypes still exist and people are instinctively quick to judge when they see a vibrant redhead covered in tattoos wearing bright 1950s dresses, but what they do not know is that I am a manager that has over 15+ years of hard work and dedication that has earned me that title. Never judge a book by its cover, we define ourselves by our accomplishments and perseverance.

This is the everyday me! No more living two lives.











We All Love Cherry Dollface

Recently, you the readers were asked who you would love to see interviewed on Pin Up Persuasion and the overwhelming response was the lovely Cherry Dollface! Many of you may know Cherry from her incredibly informative YouTube Pin Up tutorials. It is with great pleasure we have this opportunity to get to know a little bit more about the gal behind the camera…


-Tell us a about the gal “Cherry Dollface”, what do you enjoy outside of your work…

  • Work takes up so much of my time! But my work is also my hobby so it goes hand in hand. I love doing hair! I also love spending time with my new husband. We have a pretty mellow life. We love movies and making dinner and going for walks and visiting museums. I am a pretty normal gal.
– When did “Cherry Dollface” begin, how did it come to be?
  • In 2004 I was at a car show and a photographer snapped a photo of me that later ended up on the cover of a magazine. From there it just kind of took off!
– What is the meaning behind the name Cherry Dollface?
  • My real name is Cherokee so Cherry was a nickname growing up. And my email forever was CherryDollface– so it just kind of stuck.
– What/who inspires you as an artist/model?
  • I find inspiration everywhere. But mostly what inspires me is happiness. I love feeling whole and happy when I go to sleep at night so I am always searching for the things in my life that make me feel that way. I love when I get emails and messages from people saying that my videos have somehow changed or improved their lives. That gives me motivation to keep going on the days when things get tough.
– When did you get your first tattoo and what was it? Which one(s) is(are) your favorite?
  • I was 19 and I got the cherries on my chest. And it is hard to pick a favorite but right now it is my back piece because it took so long and was so painful and I am just glad it is done!
– Have you always loved the pinup/rockabilly lifestyle? When did you start embracing your love of the culture?
  • When I was 14 I learned how to swing dance and that started my obsession with vintage culture.

– If you could meet anyone living or deceased, who would it be and why?

  • I would meet Homer Simpson and share a donut and a mug of Duff beer.
– What vintage look would you like to see make a comeback with women today?

  • I think a lot of vintage looks are already making a comeback. But I would love to see modesty come back. The trend of butt cheeks hanging out all over the place is appalling.
– Have you taken any formal beauty or hair stylist training? 
  • Nope! Self taught. 🙂
– Did you ever imagine that Cherry Dollface would become what it has today? 
  • Absolutely not. It started as a fun hobby when I was in college working on a business degree. But now that degree has helped me turn my hobby into my career. I thank my lucky stars every day that I get to live the life that I do.
– Where do you see yourself in 5 years?
  • Perhaps pregnant! Oh man I am going to look ridiculous. Ha! I hope that in 5 years I am dominating the world and living a happy life with my husband and loved ones
– Do you have any new and exciting projects coming up that you can share?
  • I just designed the “Cherry Dollface” dress with Steady Clothing- it should be available by the end of the year. I am also working on doing a tour of my pinup hair and makeup classes next year. So far I am doing the mid west but I am open to other cities that want to sponsor me. And I have a really big announcement coming at the end of the year but I can’t talk about it yet!
– As a role model for women and girls around the world, what would like to share with them?
  • Just be yourself. Don’t cave to the pressures of what society tells you is beautiful or “normal.” It’s ok to feel a bit weird and out of place, especially when you are a teenager. But the more true to yourself you stay when you are young, the happier you will be as you get older.

Now let’s go with some randoms questions totally not related to switch things up…

– If you could only choose one species to save on Noah’s Ark…what would it be?
  • Koala bears. They’re so darn cute!
– Would you rather trade some intelligence for looks or looks for intelligence?
  • Looks for intelligence for sure. There is nothing less attractive than an airhead.
– What is the most unusual conversation you’ve ever had?
  • Oh man– I don’t think I can answer this one without incriminating people. My two best friends are the biggest weirdos I know, so we have lots of really random all-over-the-map conversations.
– If snakes could talk, what would they say?
  • More mice.
– What is your biggest pet peeve (what do would wish you could do to retaliate)?
  • CALIFORNIA DRIVERS!!! I wish I could teach them all how to merge. Zipper method, people!
– If you could select one person to give a million dollars but it couldn’t be someone you know…who would you choose?
  • I would go into a fire station and randomly pick a fireman. Those guys deserve it.
– Who would be more beneficial during a Zombie apocalypse – Batman or Superman? Why?
  • I have always had an insane crush on Batman, but I think Superman would take the cake. He can fly!
– If you were a vintage car, what would you be and why?
  • A 1953 Buick Skylark. Convertible. Because I look good all sparkly and topless. 🙂
– What is your favorite Barry Manilow song?
  • Mandy? Is that Barry Manilow? I’ll go with that one.


A very big thank you to Cherry Dollface for everything & I hope you all enjoyed getting to know her as much as I did! xo