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The Ins and Outs Of Casual Dressing At Work

How we dress is a testament to how we feel about ourselves

casual dressing“If we wear tight or provocative clothes, it might indicate we are seeking attention (in an inappropriate way). Or if we’re reluctant to dress-down, it might mean we’re insecure and think we can only be respected in our fully professional garb,” explains Ann Fry, executive coach and speaker.

Dressing Casual And its Implications

Because attire is so personal, managing casual days at the office is difficult. No one wants to tell you you’re dressed inappropriately for work. But, dressing too casually means that your colleagues could judge you. Even if you’re a stellar employee, crossing the line on a regular basis might indicate to your boss that you have poor judgment and that you aren’t the right person to count on.

Perception is everything. So, when rules are more relaxed at work, you still need to manage your brand and adhere to your company’s culture and values.

Here are some general guidelines to follow for casual dressing:

  • If you put something on and ask: “Can I get away with this?” the answer probably is no.
  • Never show cleavage at work.
  • T-shirts and cargo pants are not business casual.
  • If your company allows capris and sandals, wear them. But stay away from spandex and shorts.
  • Be wary of your skirt length. If it’s too tight or too short, it’s not for the office.
  • If you can comfortably leave work and go to a club or baseball game, it’s likely that you’re underdressed.

Dressing According To Your Position

A good first step is to observe what your colleagues and boss do on casual Fridays. “Like any country and nation that has its own culture and native dress, every industry and company has theirs, so like an anthropologist its important to observe what is the norm, what is unacceptable and the spectrum in between,” says Kristina Leonardi, speaker, coach, and consultant.

If you’re a recent grad struggling with what to wear on a casual day, Leonardi suggests that you err on the side of caution, dress for the position you desire to be promoted to, and constantly take cues from those ahead of you. As a new employee, not drawing attention to anything but the quality of your work will help you progress. Also, don’t be afraid to ask the basic question of what is meant by casual to set your parameters accordingly.

Caroline Ceniza-Levine, career expert at Six Figure Start suggests developing a mentor relationship with someone who knows the company well and can navigate subjective questions like this. “Business casual means pieces can be unmatched (e.g., sweater set with slacks or a skirt). Do not assume that jeans, even expensive designer ones are appropriate. Whatever you choose should be neat, pressed and polished. If you look too casual, it can be interpreted as sloppy, disorganized, unprepared, or just disinterested,” she says.

When it comes to experienced employees, Leonardi believes that you might have more leeway in terms of what you can get away with. “You’ve proved yourself so you should be more confident in your work and track record,” she says. “But you should also be more knowledgeable of what’s appropriate and how far you can push things.”

If you’re a manager or an executive, Leonardi adds that you’re responsible for setting the tone for your employees. Whatever you wear serves as an example for your team to copy. “If you’re wearing jeans and sneakers, it should be okay for your team to wear them as well,” says Leonardi.

Ceniza-Levine recommends that if executives at your company do not dress casually refrain from doing so as well. “If you do dress casually, always have a jacket handy in case a last-minute meeting is called. Business casual at the executive level still means pieces can be unmatched, but the outfit should be pulled together and polished. If you look too casual, you will not be seen as leadership potential,” warns Ceniza-Levine.

Regardless of your position, wearing expensive clothes or jewelry at any level can create problems amongst your peers, your subordinates, and your superiors. When choosing what to wear on casual Fridays, Leonardi recommends using common sense. For example:

  • Stay away from anything that is too revealing or tight (no “see-through” blouses or low cut tops).
  • Do not choose anything that needs to be cleaned or mended, or has wrinkles.
  • T-shirts should not be political or morally offensive. Your best bet is to avoid printed T-shirts entirely.

A great casual Friday outfit for any woman is dark jeans with a blazer and boots. Fry says that a loosely fitted pullover top with flats, and slacks is also a good option.

Revealing Who You Are

It’s important to acknowledge that at some point, you are bound to make a mistake. Maybe you were sick all week and your priority was to make an appearance at the office, even if you look like a mess.  Or it might be that you haven’t done laundry in three weeks because you’ve been working 15-hour days, and you find yourself with the choice of repeating yesterday’s outfit or wearing a shirt that makes you ask: “can I get away with this?”

Colleagues and your boss will forgive you for an off day, and quite possibly, two. But Leonardi warns that if your discrepancies happen on a regular basis, you risk not being taken seriously and possibly not being considered for promotions. “You can be the greatest employee in the world, but beware that people might only see your style, not your substance, especially if it is offensive or a distraction. You should find outfits that frame your personality, not overshadow it.”

Fry adds that you might be seen as a non-conformist, someone who refuses to adhere to the company’s values and norms. This negative perception leads to a lack of respect, and is difficult to overcome.

Like the quality of your work reveals your work ethic, your clothes are a mirror of your personality, and the characteristics that you want to highlight. They show your colleagues how much or how little you care about your presentation. Ultimately, the effort that you put into how you look on casual days correlates to how much you respect your office setting and the people in it.

About Carolina Baker

Carolina Baker has navigated the financial services field in New York City and London for the last eight years. Alongside her banking career, she has launched a freelance writing career, focused on career transitions, human resources, travel, and wellbeing. Visit her site for more information.


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