Case Study, Promo, Tips

How Dressing Unprofessionally Can Land You in Jail

On Thursday around 3 p.m. two Caucasian males pulled up to the Ruby, Inc. headquarters. Their Jeep was a deep green 4×4 with tinted windows and a roof rack and ladder. They pulled up the street, waited outside for more than an hour and revved their engine. One male got out of the car wearing a dark, grey hoodie, a beanie, and jeans. He was smoking a cigarette. He walked to the front door and proceeded to jiggle the handle. Then he started pacing back and forth looking in the windows. Our founder, Jasmine, called the police and reported the vehicle, plate and any identifying marks. The next day around 7 a.m. the same behavior repeated itself.

Jasmine, again, called the police.

It turns out that these two gentlemen were “professionals.” The police verified that they were independent contractors.

However, nothing about their demeanor said professional. They didn’t call and say they were coming nor did they e-mail to leave a time that they’d arrive.

Just as important, nothing in the way they presented themselves with their clothing said they were professional.

They were dressed similarly to the image below.


They wore no insignia that led to their identification. Their clothing was nondescript. As a result of their clothing and behavior, they were reported to the police.

This begs the question, how can a professional, contractor or business person who isn’t a budding Silicon Valley CEO under 30 dress in such a way as to appear professional and not scare off women?


Take note of a few simple tips to not only dress appropriately but also to stay out of jail.

  • Stay well groomed.
  • Spit shined shoes help garner a professional image.
  • In most though not all circumstances, cover body art. There are numerous budding businesses that employ hipsters and body art professionals but if it’s unusual for your industry, keep it under wraps. We, at Ruby, Inc. are big fans of body art and we also know that people may make snap judgments regardless of the quality. When in doubt, check with a supervisor or look to other professionals within your industry as a benchmark.
  • Wear identifying insignia.
  • Carry business cards.
  • Wear high quality clothing regardless of where you purchased it or the price point. Fake Rolexes make a person appear unprofessional.
  • For contractors, make sure you’re wearing an ID badge and present it immediately when working with clients.
  • Wear little fragrance. A few small spritz on a pressure point is more than enough to last all day.
  • Avoid clothing that will type-cast you as someone with a negative persona.
  • If your grandma wouldn’t approve, get rid of it.

For positive examples of businesses that send employees out to job sites, check out Two Dudes Painting Company and Lapp Electric.

Want tips to better improve your business or workforce through appearance? Click here to set up a complimentary consultation. 



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