Business suit, waist coat, and tie. That was the business world uniform from time immemorial. But no longer. These days casual wear is the uniform of the entrepreneur. I am of the age when this wasn’t the norm. If you were a business person you wore a suit and that was that. It was just the way it was.

My first recollection of someone breaking this mold was Richard Branson. In a world where a suit and tie were considered compulsory, he emerged in casual attire and the world of the business uniform showed the first chink in its armor.

Nick Alexander (left) sitting in front of computer with Richard Branson wearing pullover sweater
Nick Alexander (left) sitting in front of computer with Richard Branson wearing pullover sweater

Since then, the expectancy of business people to dress like clones has gradually eased and now we have much more freedom to express ourselves in our dress codes. But just what is the modern entrepreneur wearing, apart from masks of course? And does it really matter?

What Should Entrepreneurs Wear?

Well first, let’s put a bit of context in here. If you are going for that high powered meeting with important investors it is probably better to play it safe. Mark Zuckerberg might get away with wearing a hoodie, but you probably wouldn’t.

Entrepreneur wearing blue business suit and tie
Entrepreneur wearing blue business suit and tie

The suit is still an essential piece of kit for any entrepreneur. In the right circumstances it is still the thing to be seen in. There is a certain level of professionalism that it conveys that is difficult to beat. Ties are optional, but don’t be shy, they can still be a key accessory.

However, the range and style of suits mean you are no longer tied to that 3-piece suit with the watch chain and handkerchief. Suits are generally more casual and tighter fitting.

But of course, suits need not be everyday wear. However, that doesn’t mean that baggy t-shirts that have been through a hundred washes are acceptable for your workwear. Maybe if you’re slouching about the office on your own on a Sunday morning, you’d get away with it. But normally this just isn’t the image you want you or your business to portray.

Elon Musk wearing black sports coat over black t-shirt
Elon Musk wearing black sports coat over black t-shirt

There is a balance to be struck. Be as comfortable as you can be in your own wear, but always be aware of the image you are portraying. A great example of someone who dresses smart but keeps it casual is Elon Musk.

Keeping it Casual

Suits are ideal for those important meetings and baggy t-shirts you will get away with on those quiet Sunday Mornings, but what about the rest of the time? Those normal workdays in the office when potential clients or backers could arrive at any time.

Casual but smart is the name of the game here! For a business person, being comfortable in their own skin and clothes is important. Don’t try to be someone you aren’t; it generally doesn’t work. If you’re a polo shirt and khaki pants type person, then stick with it, being comfortable with how you’re dressed is a confidence boost in every situation.

Entrepreneur wearing blazer over dress shirt
Entrepreneur wearing blazer over dress shirt

Dress shirts and sports jackets are another timeless combo, this paring never seems to go out of fashion and the scope to express your individuality is near limitless.

Jeans are also acceptable in most cases, but they need to be good quality jeans. It is not a great image to wander into work in a three-year-old pair of generic jeans that your mother bought for you Christmas. Once again it is all about image, if you want to get taken seriously in business then first you must take yourself seriously.

Nice jeans and a quality open necked shirt or blouse can be an effective look and the scope to stamp your own mark on it is without boundaries. Many top entrepreneurs favor this as their everyday office wear and it’s another thing that never goes out of fashion. (well maybe not that shirt that has lingered in the back of your wardrobe for fifteen years)

The Steve Jobs Look

Everyone knows it and it’s another look that won’t go out of fashion. Any sort of casual sweater is great wear for the entrepreneur going about their daily business. Sweaters or casual tops can be paired with anything and are a versatile and comfortable piece of apparel.

They are also handy in emergencies when the alarm fails to wake you and you don’t have a shirt ironed. Just grab a sweater. Match it with a pair of smart jeans or pants and you’re good to go!

Of course, the type of sweater you wear is pretty crucial. It doesn’t necessarily have to be a black turtleneck, but it probably shouldn’t be the Christmas sweater with the flashing LED’s!



Comfortable and smart and matched with the rest of your apparel. Quality trainers are acceptable in most cases except suits. Or expensive dress shoes for those suit days. It is best not to skimp too much on shoes, both for your own comfort and for those lasting impressions; it is surprising how much your shoes are noticed.


Belts are a fantastic way to add a bit of jazz to your outfit and to pull the whole look together. Once again, quality is what you’re looking for. There is no point in going to all the trouble of putting an expensive outfit together then holding everything up with a piece of string.


It was simpler in the old days when everyone wore a business suit. But nowadays entrepreneur fashion allows you to express yourself and portray the image of your business to the world with a fashion statement.

For entrepreneur wear, keep it simple, keep it smart, keep it casual, and keep it appropriate. Don’t hesitate to get the suit out when required, and on a lazy Sunday morning it’s probably okay to slouch about in a baggy t-shirt.

What other fashion tips do you have for entrepreneurs to dress in 2021? Let us know down in the comments.

This article originally published on GREY Journal.