Society today seminally has become a sea of homogenous beings. Individualism has given way to mass-produced cookie-cutter thinking in almost every aspect of creative expression. Clothing is probably the best example of my assertion. Almost every culture around the world has given into subscribing to a stringent westernized dress code. Why is their so-much munkey-see, monkey-do when it comes to dressing? - Especially men!
A couple hundred years ago, before the industrial revolution, people dressed with flair and expression. Sure, societal dress codes existed, but they were very localized and seemed to offer much more diversity than today. For instance, why don't men still wear skirted garments like kilts? - Especially in the summer where it's hot. It makes more sense than heavy denim jeans or wool slacks. Think of the energy that could be save in air conditioning costs if men were not compelled to wear a long sleeve shirt, wool jacket and tie when it's 90 degrees Fahrenheit outside.
My point is, that there is less actual laws (mostly to do with decency) that prevent you from dressing how you want than voluntary societal rules. Most people worry excessively about what others might think without giving much thought to the consequences. Fist of all, most of the time you just are not going to know what others think when you break out from the pack. Second, why should you really care? - Actually, I say this because it isn't really about what others think, it is all about your personal confidence that influences more than anything about what others think.
Clothing is but many forms of expression. - But it is an easy area to shed the chains of oppression. Just imagine if you (men or women) could wear what you felt like wearing without consequence. Wouldn't life be a lot more fun? It's fun to be different. It's fun to be recognized and complimented for something unique. And it's even better to be comfortable. Maybe for you it's just going to work with a purple striped tie instead of a navy blue or red one. Or maybe you (men) are just tired of wearing pants or slacks all the time and decide to buy a kilt. - Why not? If your boss cares, then maybe that is a real consequence you need to consider. - But, on the other hand, you are not on the job all of the time. - So why are you compelled to wear a "uniform" off duty?
Even though mass retailers have homogenized so much of what people wear, you can still find different and unusual clothing through small specialty retailers and Internet sources. For instance, log onto Google.com and search "sarongs for men", "men's kilts", or even "men's skirts" and you will find links to a variety of companies selling anything from rugged workman's kilts to comfortable beach sarongs. - Oh, you will find a bunch of weird sub-culture stuff too, but if that's not you, just skip over those links. Even if you do not desire something really different, at least you can see that you don't have to follow the same fashion rules as everyone else. Everyone has a right to develop his or her own personal style.
The most important thing is to learn to be you. Don't let others dictate how you are. Develop the confidence to do what you want. Expressing your freedom of choice through what you wear is a great step in the right direction. You can use the same process to change other aspects of your life as well. Soon you will be telling yourself that you could do anything. - And then you will.