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Corporate Conundrum: What Should I Wear to Work?

10/03/2013 04:37 EDT | Updated 01/23/2014 06:58 EST

Have you ever agonized over what to wear to work or a meeting? You're not alone. This week I heard from David Wald, a social media guru and solopreneur who meets all kinds of people in his day-to-day business. He wonders whether he should dress differently for each occasion or wear the "uniform" he feels most comfortable in (jeans and a t-shirt). David's question is, "Do I have to morph my image to suit the circumstances, or is it okay to show up as the "real" me? What should I wear to work?"

This is an age-old question, David. There are no hardcore rules anymore. Ask ten people what business casual means and you're sure to get ten different answers. While some advisers will suggest that you always represent the dress code of the client, industry, or culture you are engaging with, my stance is different. After all, what's the point of squeezing yourself into a suit if doing so makes you feel and look uncomfortable? You'll just run the risk of coming across as disingenuous and underconfident.

That said, it's a fact that people will size you up within seconds of laying eyes on you. Which is why it's a good idea to do some research on the dress standards of the company or person you may be meeting or working with. But more critical, I believe, is to develop your own appearance policy. Whether you work alone or for a global conglomerate, you need to know what your personal brand looks like. Always strive to represent yourself, your profession, and your business with pride.

Here are 6 recommendations that will help you stand out and fit in:

1. Build a flexible wardrobe. Choose a variety of pieces that (a) you feel comfortable wearing, (b) mix and match, and (c) will take you into any business situation with an air of professionalism.

2. Go for quality over quantity. Invest in classic, standard pieces. Include a few trendy items, but don't spend too much money them because they will quickly fall out of fashion.

3. Be yourself. If, like David, jeans and a t-shirt describes your daily work outfit, update your ensemble with dark-wash denim, a variety of solid-colored t-shirts, and a blazer or jacket to dress things up. You'll never go wrong by adding fabulous footwear (and a dazzling smile!).

4. Experiment with different looks. Whether out of habit or laziness, many of us end up in an image rut. Stretch your limits by trying some different choices. Wear dressier (or, in my case, more casual) clothes now and again to enhance your comfort level with various styles.

5. Know where you belong. If, for example, you are interviewing for a position at a company that has a strict dress code and you're not comfortable dressing that way, you may want to reconsider applying for the position. It's likely not a good fit.

6. There's a time and a place for everything. A confident professional knows when it's appropriate to dress down or dress up. If you're not sure what to wear, ask.

Finding the right professional look is a balancing act. Set your own standards and set 'em high! Aim for authenticity and alignment with your brand, and keep in mind there's a current trend toward dressing more formally in corporate Canada. Need proof? I was at a bank the other day, and everyone - from the tellers to the receptionist - was wearing a suit. When was the last time you saw that?

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Corporate Conundrums is a weekly column providing practical advice for readers who need help dealing with workplace challenges. From incivility and unprofessionalism to learning how to how to respectfully work with a jerk, no topic is off-limits. Send your corporate conundrum to conundrums@TheCivilityCEO.com. Your question could be featured in an upcoming column!