Dressing for Success
Over time, business dress has evolved to the point where how you dress is an extension of your personality and philosophy. With the introduction of business casual and the softening of rules surrounding personal attire, people have a lot more flexibility around what you can wear at work. This is an interesting dynamic because, as we all know, image is arguably the easiest and strongest way with which we, as people, form an opinion of someone.
How does the way you dress reflect you?
Ultimately, you never want to dress beyond the bounds of the office culture – so if you work in a jeans and shirt environment you can’t come to work wearing suits everyday. Conversely, if you work in a suit only environment you can suddenly start wearing jeans to work.
For those of us, and I suspect most who are reading this post, that are looking to move up in our organization and graduate to more stimulating roles and opportunities we need to take some important factors into consideration:
- What do I want my dress to say about me?
- What do I feel comfortable in?
- What do my superiors (or people in the roles I want) dress like?
In my instance, given I am a driven individual with the goal of having roles of growing importance in my company, I take the following approach.
Clean, tidy and focused
Whether its casual dress, business casual, or more formal business attire, I always try to look clean and prepared. If you wear jeans and a polo to work – don’t wear acid wash jeans and a fluorescent coloured polo. Depending on your role, you need to select clothes that reflect that role and fit in with the rest of the organization. If you work in a creative environment, stick to something that showcases your originality. In a more traditional work environment, you want something tidy and focused.
Level of comfort
What do you feel comfortable wearing? Are you working in an environment that’s considered business casual? If so, does that mean you need to wear plain dress pants and dress shirts when you are more comfortable in a colourful shirt? I don’t believe this is true. Your clothing should be a reflection of who you are and what you bring to the organization. For example, if you are working in a banking environment, should you always wear banker blue (ie. a light coloured blue shirt), white, or some other similarly neutral shirt? Not if that isn’t your personality. If you feel comfortable in a pink shirt or a more flashy number - wear it as long as its appropriate to the work environment.
Dressing like your superiors
Arguably one of the most important aspects is how do your superiors dress? At the end of the day, they are in that role because of the way they performed and presented themselves. Thus, you should model yourself after their benchmark – but please do not mimic them. If they wear suits and ties every day while the rest of the office wears dress pants and dress shirts, make a conscious effort to wear a suit once a week or wear a tie every now and then. This is good for two reasons – one it displays your level of awareness in the importance of appearance but as an added bonus it allows you to prep your wardrobe in advance of the big PROMOTION.
My 3 rules of dressing for success
- Be conscious of the work culture and dress appropriately.
- Highlight your personality with your dress within the written/unwritten rules of the organization.
- Dress up on occasion to the level of those in positions where you’d like to be.
Cardinal sins you must never commit
- Wearing clothes that are stained, torn, or smelly.
- Wearing clothes you saw on the members of WHAM!
- Wearing clothes that fit poorly – too tight or too loose. Spend the extra 10$ for a tailor to make a dress shirt fit right.
- Wearing clothes that are identical to your bosses’.
- For women, avoid plunging necklines, high slits and short skirts. Unless you’re planning on moving up in the organization through horizontal maneuvers.
The most important rule of all
Don’t ever think dress does not matter. Although performance and results are important, a promotion might come down to which of the two candidates looks and acts better prepared for the realities of the new job.



(1 votes, average: 4 out of 5)
Great article Nick! I know when I first started my job I was very concious of what I and those around me were wearing.
I was lucky enough to have the opportunity to attend a seminar for women on how to dress for success early on in my career, here is what I learned from the fashion consultant who has worked with most of the major firms on Bay Street.
1. No sleeveless shirts; while this one is borderline be sure to take your cue from other women in the office.
2. No open toe shoes.
3. Nylons are not required so long as you are not sporting stubble and are well moisturized. She also suggested that a little self tanner doesn’t hurt so you don’t look pasty.
The last two can also be contentious, it certainly shocked a female partner in the room. She said that she was fine with open toed shoes, but if a woman showed up on her project in a skirt without nylons she’d send them home to change. Never did point out that open toe shoes look rediculous with nylons…
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