(00)7 Ways To Be Well-Dressed


Being well-dressed is not about following a set of rules and customs but about mastering communication through clothing. A well-dressed person is fluent in the language of clothing so they can say exactly what they want to say through their clothes. To truly be a stylish person and look your best in your clothes, you need to be able to speak through your clothes to develop a personal stylistic identity. Here are seven ways to conquer the language of clothing that work for any person and any personal taste.

1. Be aware of your surroundings

Dressing well doesn’t happen in a vacuum; it’s about dressing appropriately for one’s surroundings. It considers the weather, the season and the climate. It considers the activities of the day. It means following dress codes when they exist, and not disrespectfully flouting them. It can also mean dressing in colours that harmonise with your surroundings, or it can mean dressing in ways to stand out from your surroundings. The route you take is up to you, but always be aware of what surround you.

2. Be comfortable in your clothes

Both physical and emotional comfort are necessary to be well-dressed. Men’s clothing is supposed to be physically comfortable. Clothes are not meant to be uncomfortably tight, wool shouldn’t be itchy, and shoes shouldn’t be painful. But if you’re not used to wearing certain kinds of clothes, it may take time to become comfortable them. If the clothes are not comfortable, it could mean the fit is wrong or the materials are subpar.

Emotional comfort is just as important, if not more important. Emotional comfort can mean different things to different people, but it ultimately comes down to having confidence in the clothes we wear. Our clothes should make us feel like our best selves. It means not being concerned about our clothes as we wear them. Don’t fiddle with your cuff links, and don’t worry that your socks were the wrong choice. Being confident with what you’re wearing comes across as being comfortable.

3. Understand the choices you make

Know why are are dressing the way you dress. For each piece of clothing you put on, ask if it suits your surroundings and if it is right for the purpose. When you combine each piece into an outfit, do the colours go well together? Do the textures complement each other?

Learn the history of fashion to make informed style choices. The ‘rules’ exist for a reason, whether they exist to achieve visual balance and harmony in an outfit or to teach about practical clothes for certain situations. A well-dressed person can break the rules breaks, but they break them with purpose, never just because they can.

It is also important to understand why you like what you like. When shopping for new clothes, understanding our preferences can help us make better choices in curating our wardrobes. When you’re drawn to one colour over another, it might be because you subconsciously notice it looks better with your complexion. Or you might be drawn to a piece of clothing because it reminds you of something someone you admire would wear, whether that person is James Bond or your father. There’s no wrong reason, but there is always a reason.

4. Don’t get dressed on autopilot

We all make lazy decisions sometimes, but by putting in our best effort we will be well-dressed. Dressing well isn’t always about dressing a certain way, it’s mostly about trying and caring. Putting in effort is visible to other people. Do the very best you know how to do. Don’t reach for the same clothes every time, but find ways to wear the clothes you bought that aren’t as easy to wear.

5. Pay attention to fit

There’s not only one way clothes can fit, though clean lines are key to a good fit. Pulling or bagging generally signify a poor fit. However, certain trends have attempted to place fashion over fit. This can be seen in 1989’s Licence to Kill with oversized fits and in 2012’s Skyfall with shrunken fits. Neither are successful at flattering the body, but if you have a reason for liking the effect they create, that is reason enough to wear them.

Related to fit is proportion. Proportion can make clothes look more masculine or more feminine. It can make someone look taller or shorter. And it can make someone look fatter or skinnier. Poorly proportioned clothes can look like a poor fit, even if they cleanly fit the body.

Fit and proportion are powerful tools. Anyone can wear any style of clothing so long as it fits and is proportioned properly for the person wearing it.

6. Experiment

Experimentation with our clothes helps our stylistic sense grow. It’s difficult to understand what works and what doesn’t work if we don’t fail sometimes. The easiest way is to try different colour and pattern combinations. Sometimes you can take a chance with new fashions or with clothes you wouldn’t think you ordinarily like, but that can also lead to a waste of money.

7. Know what you like

Confidence in choosing clothes helps one be a better-dressed person. Don’t buy clothes just because James Bond likes them; you need to like them too. If you buy the clothes you don’t genuinely like, it’s a waste of money because you probably won’t wear them. And if you do wear them, you won’t be as confident in them and won’t be wearing them well. A key part of dressing well is knowing what best suits you, but wearing what you most want to wear will make you look good in subtle ways that show through your personality.

When you follow these guidelines, you can wear your clothes with the confidence you need to make them look good. No style of clothing is off-limits for anyone if they know how to wear it. You don’t need the most expensive clothes. You don’t need the same clothes James Bond wears. Dressing well simply comes down to dressing with purpose, intent, awareness and confidence. Following rules can be helpful, but understanding your clothes is the most sophisticated way to wear them.


  1. “A man should look as if he had bought his clothes with intelligence, put them on with care and then forgotten all about them” – Hardy Amies.

    I’m sure you have quoted this elsewhere on the website but it seemed most appropriate here.

    • I actually take exception to this quote; throughout the day a tie will loosen up, a shirt will come slightly untucked, etc. One can check and correct for those things discreetly, without giving the appearance of primping like a peacock.

      • I don’t think that goes against Amies’ quote. As long as your touch-ups during the day are done in the toilet and not in the tinted car window you happen to walk by, I see no issue with it.

  2. Nice advice to anyone on this subject! Wear what you are comfortable with and what you are interested in!

  3. Haven’t been back since a while, so, hello again, Matt!

    All great guidelines, but again, I cannot stress enough – be confident in your clothes, and be comfortable in your own skin!

    One too many times, I have seen people faltered due to their lack of confidence or comfort. It was the one thing I enjoyed in my endless combative debates in my college years. When you lack those qualities, you cannot stand against anything, let alone an adversary. Be confident, and be comfortable. Eyes wide, ears open, but also, remain consistently confident and comfortable.

    Perhaps that’s why I chose to be dressed in a three piece suit, as it is an armor for me to face the world. But maybe because it is a comfortable armor to be in, and a protectively confident armor, that made me rested assured, that I chose the suit to be my outfit. That, thus, would be the reason for my choice.

    Still wearing my suit, even for a virtual meeting.

  4. Excellent article. When I changed careers and went from being a lawyer to a professor I knew that my wardrobe could change. My suits were replaced with blazers , sports jackets and dress pants. Casual office wear was now a polo shirt and casual pants and sometimes a sweater. I kept everything tailored and up to date with the goal of being the best dressed person in the office. Then I saw that my colleagues were dressing in jeans, cargo pants and hoodies and realised I had no competition. However, I still get compliments from the other staff and students and now I keep dressing that way because its how I am comfortable dressing as a professional.


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