Dressing Well Matters

“It is both delusional and stupid to think that clothes don’t really matter and we should all wear whatever we want. Most people don’t take clothing seriously enough, but whether we should or not, clothes do talk to us and we make decisions based on people’s appearances.” – G. Bruce Boyer

It would be startling to live in a world where people met you for the first time and reserved judgment till they knew you well enough. Imagine a world where success in your profession was based solely on your competency. However, the world we live in is defined by perceptions. We are bombarded with information, time is limited and people need to make a judgement on the little information they have. Its therefore important to pay attention to the factors which build up our image, both real and perceived. Dressing well is one of the factors that require further exploration.

The psychology behind dressing well

The girl looking at you from across the cafe, the interview panel seeing you walk into the room and the CEO that is riding in the elevator with you all have something in common. They are making conscious and unconscious judgments about you. Their brain is combining experiences, knowledge and other subconscious factors in trying to build a basic picture of you. In a short span of time, they may or may not find you to be an attractive person. This becomes especially important when we consider that a number of research articles have shown that attractive people are more successful in life. When it comes to securing a job, a life partner, greater wealth, or success in general, there tends to be a positive correlation between attractiveness and success. Most of us won’t have the genetic make up of Adonis and are probably unable to afford an extreme makeover. There are however aspects of our life that we could look at to improve our attractiveness. These include areas such as our character, fitness and how we conduct ourselves in our day to day lives. How we dress is another area to consider.

Those first impressions people have of us are difficult to undo, especially when we make a negative impression. When I first got to know my wife, I did not make a great first impression especially in terms how I dress. Luckily my dressing sense improved with time and there were other aspects that contributed towards my attractiveness that she stuck with me! However, the longer we don’t do anything about our appearance, the longer we are neglecting an aspect of our attractiveness, the more likely we are to lose out on something that is important to us.

The inward benefits

The purpose of dressing better is not limited to only looking good for others. In my article on values, I mentioned that certain things will be of importance to us. Some of us try cultivate a habit of being particular about certain things. Whether its the way we ensure our car is in good working order, our finances are healthy or how we are not wasteful with food.  Dressing well is perhaps an extension of this ‘caring’ habit that makes us feel more positive and satisfied with how we are living our daily lives.

Another important association with dressing well is confidence. In her book Mind What You Wear: The Psychology of FashionProf. Karen J. Pine mentions that “When we put on a piece of clothing we cannot help but adopt some of the characteristics associated with it, even if we are unaware of it.” This in turn can affect how we feel in a situation. If I’m attending an interview or meeting, I like to be dressed well. I feel better about the way I look and that positive feeling increases my confidence tackling whatever situation may come up. At the same time, the people I am meeting are more likely to have a positive perception of me.

Whats stopping you?

We have identified several reasons to dress well. So what is stopping everyone from dressing better? There are a few things holding most of us back. Firstly, we don’t know where to start. Since we don’t know where to start, we begin to make assumptions about what dressing better entails. The best dressed people on TV and other mass media usually represent big brands and are often celebrities. This may create the impression that we need to buy expensive suits, the latest fashion items and basically spend a massive amount before getting anywhere. Lets say we buy all those expensive clothes, its still going to be quite a pain to discard all our old clothes and have to think properly about what to wear in different situations. Is it not far less stressful and less effort to continue wearing what we always do?

Secondly, some of us begin to experience feelings of anxiety and shame if we start to dress better. This happens because to an extent all of us are conditioned to behave in a certain way. What we eat, who we date, the job we hold and our other attributes (including how we dress) elicit different responses from society. These positive and negative responses will affect each of us differently but they will to a large extent shape our identity. Our behaviour will support this identity because it allows us to stay in a comfort zone. Sean Cooper from Shyness Social Anxiety provides a simple example of this behaviour within the context of clothing: “Imagine if an unpopular guy suddenly got an attractive shirt that made him stand out. He’s been conditioned that he has low social value, so the shirt makes him feel like he’s going against what other people really think of him.” Again we are perhaps more comfortable not making any change at all.

Lastly, we perhaps just don’t care. This could be because we don’t fully appreciate the benefits of dressing better. Or perhaps the circumstances we live in mean that dressing well is not a priority for us. My parents grew up in families that sometimes used to struggle financially. The focus was more on basic necessities rather then dressing well. Similarly I have memories of speaking to people and even relatives in rural India. I remember an old gentleman looking so satisfied with life on a farm with a big family. Perhaps he was living according to his values and was completely happy. Dressing better in his situation would not make him any more successful or happier.

Start the change

Each of us will have different reasons on why we want to dress better and different obstacles on this journey.  Keeping certain things in mind make this journey possible and easier. Firstly, there is no point in trying to dress better if you don’t have a good motivation to. All of us need to have a reason to do something. There must be something we are trying to achieve?  My driving motivation is the need to make a positive first impression on people and reinforce this every time I encounter them again. I also find that dressing better is one of the factors which increase my confidence.

Secondly, start with smaller changes. This eases us away from the social conditioning we are used to (in terms of how we dress) and places a lesser burden on our wallets. A simple way for men to easily improve their look is to wear a polo shirt as opposed to a t-shirt. My wife improved her image at work by switching from a jeans and top combination to trousers a blouse and blazer. This was done through a combination of smart purchases and reusing existing clothes. These incremental changes allow us to ease into the process of dressing better and at the same time we are able to experiment in terms of what looks good on us.

Thirdly, purchase clothing with a view of them as investments. Yes, you might spend more upfront but these clothing items should look great on you and last for a long time. Antonio Centeno suggests using a style pyramid when deciding on what clothes to buy. “If something doesn’t fit, stop there. If it fits, but it seems cheaply made, skip it. And if it fits and is of good quality, but doesn’t feel right for your style, wait for something more suited to your tastes. When all three intersect — then it’s time to buy.”

Lastly, be aware of the situation and adapt your dressing accordingly. When going to a fancy restaurant, on a hike or to work, we need to dress appropriately. There are numerous articles, books and videos that can help with improving your dressing sense (some of these links are provided below under references). In fact there is more information and support available over the internet then ever before. Depending on your perspective dressing well is not a complicated process. Its about adhering to certain principles over a period of time.


Alpert, J. (2013, Oct). Fearless Self Image: How You Dress Matters

Centeno, A. (2013, April). Save Money and Shop Smart: Know the Style Pyramid

Centeno, A. (2016, Sep). Why Give a Damn About Appearance

Cooper, S. (2012, Jan). Why Shy People Are Afraid To Wear Cool Clothes

Dion, E. (2013, Aug). Dressing Well and Why it Should Matter to You

Ferguson, JL. (2016, Feb). How Clothing Choices Affect and Reflect Your Self-Image

Pine, KJ. (2014, May). Mind What You Wear: The Psychology of Fashion

Tervooren, T. (2014, Mar). The Psychology of Dressing Well (And Why You Must To Get Anywhere In Life)

Williams, DK. (2013, Aug). First Impressions Count: The Business Value Of Dressing For Success