Do you need to navigate the world of ‘political dressing’? Jackie O’Fee asks if you should dress down in order for your boss to shine.

All of us have things in life that specifically interest us. There are the things we love, the things we enjoy or the things we simply exercise a greater degree of attentiveness toward. 

Perhaps you love cars and what you drive is important to you, meaning you will opt for a special model while many others will happily drive something that gets them from A to B. Maybe you can literally spend hours sourcing the ‘perfect’ lamp for your living space, while others among us are just as happy with a basic ‘light’ bought from a chain store.

Clothing affects us the same way. Within any larger organisation there will be those who love fashion and clothing and will always make an extra effort with their ‘look’ each day. Within the same organisation there will also be those for whom choosing what to wear every morning is more a matter or what’s clean or what’s easy.   

This is why you’ll find the hapless, ill-fitting suit wearer at the desk beside the perfectly turned-out team member. This is also why the interpretation of your company dress code appears to have so many variables, with those who just appear to ‘get it’ and those who simply don’t.  

What do you do when your boss isn’t interested when it comes to matters of fashion and style, but you adore the whole process of getting dressed for work?  Can this be career limiting? 

The good news in this situation is that many people who aren’t ‘into’ clothes are often blissfully unaware of how well or otherwise those around them dress, leaving you free to dress how you like. Some bosses actually enjoy the reflected glory of having a stylish employee in their team.

What can be more complicated though is when it is political for you to be a supporting actor to your boss’s leading role. If your clothing choices and grooming garners you publicly spoken compliments and additional positive attention when attending events or meetings with your boss, is it a problem?   It is, if you feel that your boss may be feeling a little resentful of the attention. 

Do you need to navigate the world of ‘political dressing’? Should you dress down in order for your boss to shine? 

Interestingly, given your boss has an influence on your career progression it would seem the answer here could be yes. Mirroring those we wish to influence is a well-known non-verbal communication method to make others feel comfortable and to trust us. The manager/subordinate relationship is, if nothing else, one of trust. With that in mind, it may pay you to dress more like them than not. 

Although I’m not suggesting you ever dress like a scruff at work, it may be a good idea for you to ‘play down’ some elements of personal flair. In this circumstance perhaps choose a more understated guise rather than a flamboyant one and eschew strong fashion-forward looks for those that are more conservative. 

While you should never be poorly groomed, if your female boss chooses not to wear make-up and you are a make-up wearer, perhaps choose a more understated lipstick and softer eye shadow tones. 

In a perfect world, we would all applaud our differences, however reality suggests what sets you apart in a positive way with many people may set you apart in a negative way with others. Like that passion for cars or interior design, it’s all down to our personal points of view.   


Jackie O’Fee is the owner of personal style consultancy Signature Style. She works with both individuals and organisations.

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