What I Learned Dressing As A Woman

 
The twin sister Sarah Call always wanted.

The twin sister Sarah Call always wanted.

 

Drawing Names
I pulled the small piece of paper out of the bowl and shielded its content from those around me.  “Sarah” it read.  I died.  I thought, "Was I man enough to pull this off?"

At my previous employment, the marketing/finance department was a very diverse crowd.  We thought it’d be fun to draw each other’s names and dress up as that individual for a day.  And me, a man, drew a woman’s name, Sarah Call.  Did I mention she wasn’t a man? 

My coworker, Sarah Call, is very fashionable.  She’s loves dressing vintage and often times scours thrift stores to find original 1960’s pieces of clothing that she dawns with her cat eye glasses.  At first, I didn’t like the idea dressing as a woman, particularly someone as famine as Sarah Call.  You either go big or go home so I went big.  

The day came when we all of us showed up as our fellow coworkers.  Woman as men, men as woman, and everything in between.  And we died laughing.  It turned out much better and funnier than we had anticipated.  To dress up as someone, we had to exaggerate or characterize their unique traits, behaviors and clothing.  And with that, came some realizations:

People started to doubt their own confidence in the presentation of themselves:

  • Do I really dress that weird?
  • Is that what my jewelry looks like to you?
  • Do I look like I dress like I’m stuck in college?
  • Why you doing a lazy eye in the picture?  Do I have a lazy eye?
  • Do I come across to you guys as some meat head?
  • Am I really that boring to dress up as?

People feared others’ responses:

  • Do you think they’ll be offended if I dress with this?  
  • I know she loves this style of clothing, but will she think I’m making fun of her?
  • I hope they realize we love this about them and I’m only exaggerating a little.
 
Everyone dressing as another coworker.

Everyone dressing as another coworker.

 

Focused on the positive:  
It was fun brainstorming with others how to dress as another coworker.  The cool thing was, the conversations ALWAYS focused on the positive, the things and behaviors we loved about that particular person.  Negativity was never part of the conversation.

 
It didn't take long for the creative department to get a hold of these candid shots, airbrush makeup on my face, photoshop me holding a hand bag, and them e-mail it out out to the company.  

It didn't take long for the creative department to get a hold of these candid shots, airbrush makeup on my face, photoshop me holding a hand bag, and them e-mail it out out to the company.  

 
Peder's interpretation of how I dress for work.  Pretty close. 

Peder's interpretation of how I dress for work.  Pretty close. 

Validation:
The best part of this experience was critiquing everyone’s “dress-up” and sharing with the in individual WHY we loved that part of them.  It’s one thing to say, “I really like that shirt you’re wearing today.”  But it goes so much deeper when we took a person and tried to mimic as best we could how we viewed them.  And then to add, “THAT'S what we love about you!”

Conclusion:
I don’t plan on dressing as a woman in the near future.  It was awkward enough trying to pick out “Sarah Call” clothing at Ross.  But I do plan on being more confident of my own uniqueness.  And more appreciating of others' presentation of themselves.