We live in an informal age. Service people who don’t know you (annoyingly) call you by your first name, and the preferred mode of dress is decidedly casual. However, to dress casually does not mean giving casual regard to the way you dress. In an era when there are dress jeans and fashion sneakers you still have to give some attention to how you put yourself together. Obviously you never wear sneakers, fashion or not, with a suit. Once in Rome a man in a suit and sneakers outside a restaurant urged us in. That should have been a red flag. But initially I thought that perhaps it was some kind of new fashion statement, given that the Italians are the most stylish people on earth. But it wasn’t. The restaurant was terrible, and the guy was just a dork. To avoid looking like one yourself never dress that way.
When it comes to jeans it is just amazing how much effort people put into making their jeans look worn when new, as though they were used in some kind of manual labor. That being the case, it makes a lot more sense to wear the jeans that people who really do such work actually wear, such as Levis, Wranglers, Lees, etc. than an expensive label. However, if you really want a worn look it makes more sense to buy a used pair of jeans, at a much lower cost. Working jeans are okay to bunch a bit on top of a pair of sneakers. But if you’re going to wear fashion jeans, they have to be fitted properly, or their stylishness is lost, particularly in a color other than blue. That means having them hemmed, if necessary, to a proper length, so that they don’t crumple up at the bottom. They should flow down from the hips and fit more snugly than dress pants. Baggy pants hanging from the butt look ridiculous. Should the belt go over or under the label? If it’s not sewn on, it’s meant for the belt to pass through, and given what they cost, you might as well let it show if it’s not too loud. On the other hand, if the name or signature emblem is all over the pants, shun them to avoid becoming a walking billboard for someone else. If you’re going to advertise for them they should pay you, not the other way around.
This applies to other articles of clothing as well. Designer names prominently spelled out on clothing are tacky. Rather than appearing fashionable, you appear to want other people to know you just think you are. The reason to pay a premium for any kind of designer wear ought to be based upon quality and stylishness. It doesn’t matter whose name is on it if the material isn’t good and it doesn’t fit well. There are, unfortunately, some designers who allow their names to be put on inferior goods, so you need to examine the article carefully. What is it made of? Where is it made? How well is it made? The only reason to ever purchase a costly label should be based on quality. Is this item intrinsically worth the cost? If not you’re just throwing your money away. You should only pay more for quality goods, not brand, unless it is one you trust in that regard. Wearing clothing that is higher in quality is far more stylish than wearing a label that claims to be.
It makes no sense to spend an obscene amount of money on a pair of Louis Vuitton sneakers that are not particularly well made and can’t justify such a high price, just because of the label. Prada, on the other hand, is at the top of the fashion sneaker heap because the shoes are well-made in Italy. But even they have started selling some that are made in Vietnam, albeit at a somewhat lower price and different design. You don’t want to pay Prada prices for lower quality goods. In any case the most important consideration should be comfort, and if that works it doesn’t matter what the brand is, especially if they are white. Once color, or more intricate design becomes a factor then the label may matter more, but again only to the extent it represents actual style and quality that doesn’t have to be broadcasted. It is just juvenile to walk around with something that loudly proclaims “Look who I’m wearing.” For that seldom says what some people foolishly think it says.
If you’re not working on a sailboat, don’t wear shoes without socks. It is gross, and besides contemporary shoes are designed with the assumption that socks will be worn. Not wearing socks is bad for the shoes and bad for your feet. Obviously this does not apply to sandals, which, on the other hand, look goofy when worn with socks. Flip flops used to be called Japanese shower shoes. That is what they were intended for, to come and go from the bath or the beach. Wearing them almost any other place such as the street is inappropriate, as well as dangerous. Unfortunately you do see people walking around city streets these days with flip flops but all it says is that they are clueless and have no class.