If you are going out on a date you dress to impress. If you are going to a business function you dress to look the part. If you went to a business function wearing tight leather pants and a leather vest you would probably not be well received, that is, unless you are Channing Tatum. You would attract a lot of attention, but not the right kind of attention.
Fashion also changes all the time. It used to be fashionable to wear powdered wigs. Fortunately, that fashion statement ended over a century ago. I do not consider myself to be an expert on fashion but I am at least able to wear the right colors together. I know that socks and sandals are considered a fashion faux pas. Most people accept these unwritten fashion norms as law. What surprises me, however, is the unwillingness of people to invest the same amount of time and energy into their website as they would their clothes or haircut.
Your website is a virtual extension of you or your business. In today’s modern world people will often visit an individual or business online before they visit them in person. Your website will often be the first thing someone sees before they physically visit your store. If you do not have a brick and mortar store than it is even more important that your website looks impeccable. People are going to make their initial judgments about you or your company based off of what they see online. Just like fashion, web design changes as well. What used to be a good looking website in 1999 is probably not a good looking website today. So, unless you want to get the awkward stares and bad snap judgments, I’d recommend keeping your website (and your closet) up-to-date.