There is a try.
My wife and I were out for dinner last night for her birthday. I found a restaurant in Salt Lake that had a very private atmosphere and would be a nice place to eat without breaking the bank. I love going to a good restaurant and tasting the difference between a real strip loin steak and the crap you get at Chili’s on an average weekend. We eat out less often so we can get more bang for our buck when we do.
We were tucked into a corner table where we had a decent view of all the other people in the restaurant and it was a nice enough place that the majority of people there were relatively dressed up. No suits and ties on the men, but a lot of dress shoes, dark jeans and sweaters.
Two tables down from us we spotted a relatively young couple who looked to be on a first date. They were probably both 21 or 22. The girl looked as dressed as most of the other women in the place – skirt, tights, boots, hair done, etc. (It really is nice to live in a city where there are so many thin, attractive women who take care of themselves.)
Her date, on the other hand, looked like a complete disaster. The kid was scrawny to the point of looking like he was almost sick. He had on a short-sleeve, button-up shirt that was some muted maroon and he had every single button done up without a tie on. Over that he had a brown vest that was too small and showed his shirt billowing out above his pants; generic leather belt and brown, pleated pants that were twice as baggy as they needed to be.
The funny thing about this kid though is that you could tell he was dressing up better than those around him. He wasn’t trying to be as casual as possible while staying within the acceptable bounds as most of the other men looked to be doing, he was making an honest effort to dress up.
My wife and I both instantly liked him. It got us talking about seeing those same efforts in other aspects of life. A huge example for me is when I work with people who don’t speak English. It frustrates me to no end when I sit down with a customer who knows I speak Spanish and makes zero effort to even address me in English. Every minute with them is irritating. But when I have a customer come in who speaks terrible English and insists on speaking English, I will spend two hours with him making every effort I can to make sure we understand each other. My respect for someone who at least makes the effort to try is so much more than for someone who’s too scared or too arrogant not too.
Dressing well is similar to learning a new language, at first you’re going to make a lot of hilarious and embarrassing mistakes. Then the mistakes will even out with your actual knowledge. If you get over the trepidation and really commit to it, eventually your experience and know-how will outweigh your mistakes and finally you won’t make any at all. Knowing that someone is going to respect a failed effort more than no effort at all should make it even easier to start trying to improve on your outward appearance.