Digital Trends: Dress Up or Down?

Updated: Nov 20, 2018



The global FinTech community gathers in Singapore this week for the #SingaporeFinTechFestival. These are bold entrepreneurs who take on financial risks in the hope of a big break with their #startups in today's digital age and digital cash economy.


Call it occupational disease, I do have a tendency to check out the mens' dressing. Most often the guys are seen in sporting casual looks like untucked button-down shirts, faded jeans, sports kicks or slip-ons, which is pretty cool. Surprisingly, i did notice some individuals smartly dressed in sports jackets which is actually very tasteful. So, here I raise a question: how do we dress up in the digital age? Particularly, if you represent an up and coming brand/company, how should you dress up to reflect the times and the "coolness" of owning or working for a startup?


Mark Zuckerberg and the late Steve Jobs were famously known for their simple attire of jeans and tees when they appeared in public. Question is, if one is seeking more than $1 million dollars in funding, do you stroll to a meeting wearing relaxed garb or do you dress appropriately?


There is an industry notion that going into a meeting to seek million-dollar funds and deck out too fiercely, you might look too trying to impressed. However, to some serious investors, appearing unpolished can leave a terrible impression to the middle-age investor. Clothes do maketh the man, and it speaks much about one's self-respect and grooming. Of course, I am not dictating a full suit and tie but a nice crisp long-sleeve textured shirt tucked out over a linen sports jacket with dark jeans and a sports kicks, would probably do the trick to exude a certain kind of ease and confidence. Needless to say, flip flops and bermudas should never be the sartorial dialogue whether you are meeting an important impresario or a private investor.


The thought of starting your own company can inspire people and the sky's the limit in terms of financial aspirations. But somewhere in that list, isn't there the added perk of limitless self-expression, particularly in terms of wardrobe?


Perhaps people have taken the workplace and meetings too casually, or have they taken it for granted, opting out swanky office attire for a relaxed and informal approach? Over the last decade, the workplace and meetings have become a lot more relaxed and informal," says Patty Buccellato, a certified image professional based in Rochester Hills, Mich. "The downside, though, is that many entrepreneurs have stopped making exceptions to this routinely casual style, especially when they are seeking funding. Unfortunately, these miscalculations often don't register until people get negative feedback and the damage has already been done.",


Some individuals feel that they don’t need to dress sharp as a sense of doing business, but i believe there’s some negotiable middle ground for some apparel to be a little relaxed. The point is that whether you dress up or down, you can always look good. I say is it about dressing right and here’s some guidelines.


Dress for the occasion. Your upper management might feel a casual get-up might not be ideal for the brand representation. Always know the situation you’re in. Is it a video filming for a company’s Youtube posting? Then clearly, you’d want to be in something more appropriate than khaki shorts and polo tees.


Do no appear under-dressed. It is better to overdress than underdressed as you never know who you will meet or bump into on the street. Of course, you also don’t want to be in a three-piece suit all the time. The key is to always be neatly dressed and to your style.


Find your style. Whether it’s formal or informal, an eye for detail helps. You don’t have to copy someone's style just to keep up with the Jones. Find your own personality. If you’re in a sales job, why are you not winning clients? What is the persona you want to project with your dressing?


“Break” into the clothes. If you’re not used to wearing a two-piece suit when you’re required, try breaking into the get-up by wearing them at home. Like what you see in the mirror as you dress, before you know it, you would be feeling more comfortable walking around in them.


Being authentic. It may be more about casual versus formal attire or the other way round, it’s more about being authentic. Know your audience – are you pitching to the VP of a client’s brand, or are you giving a TED talk to a bunch of interns? Also know the role you’re in. Clearly, a computer geek/programmer can get away with a T-shirt and jeans, but a VP for partnerships might require a more sophisticated sartorial ensemble.


While self-expression is reserved for one’s personal life, how you dress is what people view you for, after all, first impressions count. The T-shirt and jeans attire for the modern start-up might soon be a thing of the past because when you value what you wear, you start to also respect the person you’re playing host to, and vice versa.

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