How do you define "well-dressed"?

Last week, my sister-in-law Jill sent me a link of The 40 Worst-Dressed Cities in America. This led me to think how we define "well-dressed" in our society. Is it money? Is it brand? Or is it just how you feel yourself? I have my own take on this.

First of all, I think if you are OK with what you wear, labels such as best-dressed or worst-dressed simply do not matter.  Looking at the photos from the link above, to me these people appear comfortable and happy. There is nothing wrong with it! And some of them clearly don't care what other people think of them! Good for you! There is nothing wrong with wearing clothes to express yourself.

Second, I think it is quite important to dress for the occasion, whatever that occasion might be. Imagine if you are the only person who wears an evening gown to a football tailgate party, or if you wear your football jersey to your son’s graduation. Don't get me wrong, if you are happy with yourself, it is OK. But if you are not intending to express your unique personality through your wardrobe, following a common sense dress code is not a bad idea. There are exceptions too. I heard this story from my husband. A famous billionaire property investor wore jeans and an open-necked shirt to speak at an investment conference where suits and ties were the dominant style. Clearly, he is not concerned with being underdressed, and that is OK too.

All that said, most of us still live in a world where we deal with people, and those people’s opinions matter to us and may well directly determine our success, whether we get the business, the promotion or the date. If we are not where we wish to be in life, part of trying hard may well mean presenting your best possible appearance. A salesperson, to take one example, needs to project professionalism and credibility. In an ideal world, a potential buyer would see past appearances and judge objectively and solely on the merits of a given proposal. However, there is plenty of evidence that shows that people’s initial impressions come from the first five to ten seconds of meeting someone, and that these are extremely difficult to change once established.

What type of image do we want to represent ourselves? That may well depend not only on oneself, but also on who is in the group with whom you are interacting. A salesperson approaching a law firm, for example, may well dress differently than one approaching a musician or an internet startup. There are still some general guidelines one can follow - it is generally a good idea to be no less dressy than the customers you plan to call on. Here are three basic key guidelines for looking good in general:

1. Fit! Sleeves, hem, waist, inseam etc are all very important. If they are too loose, you appear to sink yourself into the clothes; if they are too tight, you could look like you have “sausage rolls” on your back - this is clearly not a good look! Reasonable balance, and the right type of camouflage and accent for your individual body type are the keys to the ideal fit.

2. Color. Color is the essence of dressing well - it affects how you feel and how people respond to you. Color attracts the eye first. It is the first thing that others see about you and probably will remember about you. The right color will light your face up, and make you look bright and energetic. The wrong color will emphasize more of your wrinkles and dark circles. Understanding and using the magic of your individual color palette to express yourself will empower you to look and feel better and healthier, and evoke a positive energy around you that will make a good impression on those you meet.

3. Style. This is the most challenging to discover and manage. Many of us go through stages with our style and it is OK. Don't be overly self-critical. Our personal style usually evolves over the course of our lives. As we shift priorities from ourselves, to our career, to our families, and sometimes back and forth among these, how we express ourselves and our style may well change too. If you feel more comfortable with a timeless, classic look, go for it! If that bores you, you can try for a more creative look. You need to learn through your own experimentation and experience what is best for you - no store salesperson or magazine can decide this for you. The only way you can wear clothes comfortably and confidently is to find your own style.

Readers, I’d love to know what you think! Please share your ideas in the comment section.