Guest Post: The Dilemma of the Self-Employed: What to Wear to a Face to Face Meeting?

Elizabeth Friesen  is a Toronto-based image consultant, stylist, speaker, workshop facilitator, performer, writer, and consultant to the hospitality industry. Please feel free to contact her at brightredfirecracker@gmail.com or follow her on Twitter (@EMFriesen).

You work from home or from the coffice (Coffee Shop Office). You’re not tied down to any single employer or bricks and mortar workplace. You pitch ideas over the phone, via email or Skype. You are your own boss and it’s what you’ve always wanted! That’s great! But wait! A potential client wants to meet you in person. As you look down at your stained sweatshirt, torn jeans, and flip flops, you realize that what you’re wearing isn’t exactly appropriate for your upcoming meeting. What do you do? Here are some general guidelines to help you get started.

The first step is to research the culture of the organization for which you hope to work. As much as we all feel that we should be assessed on our skills and merits, the truth is that potential employers take image into consideration as well. If you fit the image of the company you hope to work for, you increase your chances of finding employment within that organization. Whether or not you are employed for a month, a year, or a lifetime, your attire should reflect the stylistic sensibilities of your employer. You are expected to be a visual representation of their ideals, not your own, so be prepared for the possibility that you might not get the job if your appearance is deemed inappropriate.

Like it or not, a corporate culture generally demands conservative conformity. Unless you are specifically told otherwise, if your client is corporate or professional, you will be expected to wear a business suit. It should be classic, tailored, conservative in cut and style, with clean lines and without any embellishment. Traditional colours like navy blue, black, or charcoal grey are the norm. Your footwear should also fall within these same guidelines. Accessories should be minimal and tasteful. This is not the place for visible tattoos, piercings, excessive makeup, or outrageous hair.

Certain companies allow for much more flexibility and individual expression. If your client operates in a more casual or creative environment, I would suggest a smart casual outfit. You still want to look confident and pulled together, but you can have a lot of fun with colour, edgier cuts and styles, great shoes, and bolder accessories. The expectation here is that your clothing is a reflection of your creative abilities.

If your client falls somewhere in between corporate/professional and casual/creative, your best bet is to wear a business casual ensemble. Take your tailored business suit, remove the jacket and tie, and replace it with a pullover, cardigan, or unstructured jacket in a different material. Introduce pattern and texture. Wear chunkier jewelry, more interesting shoes, and creative accessories, but exercise some restraint. In this type of environment, the key is to look current without appearing too trendy.

For an introductory meeting, I always say that it is better to be overdressed than underdressed. You can always remove a jacket and tie, loosen your collar, and roll up your sleeves, but you can never turn sweats into a pin-striped suit. I shouldn’t even have to say this, but I will: never wear anything that is torn, frayed, stained, faded, dated, tight, shapeless, short, sexy, or age inappropriate. Just don’t. I certainly don’t want to quash anyone’s freedom of expression. I just want you to get the job.