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The Entrepreneur’s Code to Dress for Success

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Section: Dressing for the Occasion - Blog

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There was a time when the word entrepreneur evoked images of men in tailored suits running to and from business meetings briefcase in hand. These days, though, it’s more likely to bring to mind thoughts of men dressed in imitation of Mark Zuckerberg looking to sell their latest dot com venture.

In a world that’s not quite as cut and dry as it once was with regards to style, there are more questions than answers. Should you dress like you don’t care, or should you dress to impress?

Well, this all depends on the nature of your business and the people you are meeting with, so to cover all the angles we’ve come up with a list of wardrobe essentials and the occasion they are suitable for.

A blazer

Whether it’s navy or black, the blazer is a must have item in any entrepreneur’s style arsenal. Ideal for business or social meetings, the blazer is your get out of jail card when you arrive to find you’re at a jacket and tie affair.

You can dress it up or dress it down or wear it with chinos or a pair of jeans. Just make sure you have a tie stowed in your briefcase should you need it.


Perfect for – casual client meetings.

A good pair of jeans

Forget those once fashionable distressed jeans you love so much and invest in a pair of stylish, heavily dyed jeans in a darker colour. These are an ideal way to appear more casual and relaxed yet still smart enough to give you a more refined dressed down appearance.

Perfect for – casual client meetings, conferences, exhibitions.

A tailored shirt

The ideal companion for those jeans is a custom made business shirt. It adds an air of elegance to a casual look and is quite the professional-on-a-day-off look.

Pale hues are the way to go, and we’d even go so far as to suggest at least 5 or 6 of various shades in your wardrobe. After all, you’ll likely wear them with your suit.


Perfect for – casual settings, formal meetings.

A tailored suit

The world of the entrepreneur is one of meeting after meeting with potential clients, investors, and business partners. And in this world, impressions count. A tailored suit that fits you perfectly gives off the right air of professionalism, which is especially useful when trying to convince people to part with their money.


Perfect for – presentations, meetings with your bank manager and investors.

A quality briefcase

We’ll assume that you already understand the importance of having enough space to carry around your daily essentials and move straight to the appearance of your briefcase. Make sure it is in good condition and if it is leather, that you treat it regularly with wax. Try to purchase one that has more than a modicum of style, and if using an old one, make sure that there are no scuffs or scratches on display.


Perfect for – every meeting you will ever attend.

A versatile pair of shoes

A pair of shoes that are both comfortable and stylish aren’t always the easiest to find but find them you will. As an entrepreneur, you will most likely spend a lot of time on your feet, and a pair of shoes that pinch your toes or heels will only make you irritable.

But try to buy shoes that will look just as good with your suit as they will with your jeans. A dress boot is a good option but so too are low heeled wingtips and brogues. And keep them shined.


Perfect for – all occasions.

An entrepreneur’s life is full of decisions with each one, no matter how small, playing a significant role in your day. But there are certain decisions that you can free your mind of, such as what to wear to a meeting. Add these items to your wardrobe, wear them as we suggested, and you will have one less thing to worry about as you navigate your way to success.

You can always count on us to offer you one-on-one styling advice. Just stop in our Sydney showroom or schedule an appointment at your convenience.

Image credit: © Ifeelstock | Dreamstime.com © Elnur | Dreamstime.com


We tailor make mens suits, jackets and shirts for all occasions. Each garment is custom designed, precisely made-to-measure and is guaranteed to fit you perfectly. Unlike others, we offer you end-to-end service and a personalised styling session where we take the time to understand your needs to ensure you get the colour, style and fit you want.

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Named in GQ Magazine's "Best Tailors" list, and the highest reviewed tailor on Google, Montagio has paved the way for discerning men to get suited up with style. We offer a truly personalised experience, specialising in custom designed, perfectly fitted suits, shirts, coats, and shoes for for business, weddings, formal and casual events. Our showrooms are visually packed with designs that inspire plus thousands of fabric options, making it easy for you to get the look you want. Our expert stylists will advise and professionally fit you and frankly won’t let you walk out until we’ve tailored your perfect garment. Since 2010, we have custom tailored looks for thousands of happy customers. To experience the same red-carpet service, book your personal appointment today.

Steve Fambo

Hats off to the team at Montagio Custom Tailoring Sydney. I was immediately impressed once I stepped into their boutique showroom... more »

Scott Lasak

The suit and shirts I received were terrific and much better quality than ones I've found in stores off the rack. I would absolutely recommend them... more »

Yun Zhi Lin

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