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Men's Style Blog

From Team Member to Manager – How to Dress Like a Boss

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Making the move from being a team member to a management position is one of the most difficult steps to take on the career ladder. It’s a transition that puts you at odds with your former peers and under the scrutiny of c-level executives.

But there is a way to ease the tension in your new-found position, and it’s quite simple; dress like a boss, and here’s how.

Plan your outfit like you would a project

An upgrade in position should mean an upgrade in your wardrobe. People naturally expect something different from you now that you’re management, and the easiest way to meet these expectations is to do so visually.

Before your first day in your new role, sit down and plan what you are going to wear for the entire week. This removes last minute decisions from the equation and means you wake up each day with one less thing to worry about.

Visit a tailor

Even if you wore a suit in your previous role, it’s time to make a change. Take things up a notch and have a suit tailor made rather than purchasing one off the rack. The tailor will choose the best fit for your body and can help you choose fabrics and colours that will suit your industry.


They can also help add a few personal touches to your suit that will set it apart from your team members’ outfits. Coloured lining or even a new lapel style will work well as an understated break from the norm.

Dress like your peers

Take a look at what all the other management level staff wear each day and take this as your starting point for your choice of attire. Aim for the same level of formality and if it is a conservative workplace, don’t stray too far from traditional business wear.

This doesn’t necessarily mean you cannot have your own individual style, but as a new recruit to the ranks of management, you want to earn your sartorial stripes rather than look like a strutting peacock.

Choose subtle accessories

Gone are the days of a tie being the only accessory you knew of or needed. Now that you are a manager, you need a few more items to pad out that suited look.

Pocket square – Remember not to match the square to the tie. Your square can match one element of another component in your outfit such as a stripe in your tie or even a stripe on your shirt.


Tie – Choose power colours such as red, green, or blue and keep it simple. If you are going with a patterned tie, then choose a classic stripe, and for the love of all that is stylish, nothing sports related.


Cufflinks – A nice addition to your outfit and one that adds a touch of class. But as with all other accessories, they should be quite subtle. Avoid club and school cufflinks for the time being.


Watch – Unless you are married to your current timepiece then a new one is a good idea. It’s another one of those visual changes your staff expects to see and is also a nice reminder to yourself that you made it. Choose a dress watch that fits in with your personal tastes, and if you want to show some real sartorial swagger, match the wristband with your belt.


Shoes – Again, this is another one of those noticeable changes that affirms your role in the ranks of management. Oxfords, either brogue or wingtip, will do and make sure they shine like new each morning.


Starting a new role in management is difficult. You want other managers to respect you and your old team members to take you seriously. We’re not going to lie; it’s going to be tough for the first couple of months.

But by following our tips and taking a new approach to how you dress, you offer your colleagues a first impression of you as a manager that is sure to make them sit up and take notice. For more personalised style advice, stop by our Sydney showroom or schedule an appointmentwith our stylists.

Image Credits © Daniel Nagy | Dreamstime.com © Alexei Gridenko | Dreamstime.com © Oleg Tovkach | Dreamstime.com © Dmitriy Shpak | Dreamstime.com© Elnur | Dreamstime.com


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