I find when a lot of men want to start dressing good, they tend to look to certain guides online that call for wardrobe “essentials.” These guides usually look the same, with a couple basic oxford-cloth button downs, a pair or two or chinos, a pair of black and blue jeans, a couple of T-shirts in neutral tones, a pair of sneakers, and an inoffensive yet “cool” jacket. These guides are not bad, and could easily benefit the less style-conscious man into understanding a basic (albeit fairly conservative) conception of the contemporary men’s wardrobe. Where I object to these guides is where they’ve been interpreted to be understood as how stylish men dress, rather than being a bland and unobjectionable style of dress (at least according to conservative social mores), and how this understanding of fashion can lead to the rejection of the weird or experimental.
This isn’t to decry dressing “normal,” or minimalism, or any other genre or dressing basically that’s become synonymous (at least in certain social contexts) with having good style. Basic items are useful at building outfits, and to those inexperienced with creating interesting silhouettes, they provide excellent building blocks to understand how to build outfits that subvert fashion “rules” in interesting ways (where I’d argue some concept of individual style actually comes into play). What’s bad is when basic outfits define what is good, and that anything experimental or different is scoffed at for being ridiculous, stupid, or, perhaps worst of all, pretentious. Is there anything more ridiculous and pretentious than pretending that certain styles are “classic,” as if even the most basic hallmarks of the modern wardrobe haven’t been dramatically reinterpreted and made trendy in new ways over time?
There is a lot to praise for avoiding trends. Fashion could do with a slowing down, and many positive possible outcomes can be produced by such an effect: sustainability, better working conditions and wages for clothes makers, and higher quality clothing can be outcomes of consumers buying more basic clothes that they will wear for years (and not just a season). At the same, I think there’s more to the obsession with “classic” clothing than a simple avoidance of trends. Firstly, “classy” people (a designation buried with a slew of morally repugnant elitist connotations) tend to follow trends, even if they’re unaware of it (we’re seeing this now with the slow move away from super-tight fitting men’s clothing). Secondly, and in relation to my first point, I think that dressing “classic” is less about avoiding trends (and perhaps being interested in better consumer practices), and more about being uncomfortable with the weird.
This is why I separate the categories of basic and normie. Dressing and understanding basic conservative dress is how we can develop style, or how styles of subcultures can define themselves against conservative norms or fashion rules. You have to know the rules to know how the break them. Dressing (or perhaps thinking) like a normie suggests an aversion to subversion, an arrogance and ignorance towards the ways that fashion changes, and a irrational dislike of those who dare to be different. I do not mean to suggest with my editorializing that anyone who doesn’t dress experimentally or have their own unique style should be ashamed (such contrarian hipster attitudes have their own problems). What I want wish to convey is that you don’t let your comfort with basics make you shun the weird. It sounds awfully corny, but the weird is a space where we can find new ways of experience, giving us new ways of expressing ourselves that we may not have thought of previously. The weird can truly be emancipatory, even in the form of clothing. Shutting out the weird in any aspect of life is a poorly-made decision, and fashion (and the aesthetics associated with it) should be no different.
You should not live your life worrying that people will look at old pictures of you and laugh at the trends you followed, and how silly you looked with those pants or that hairstyle. Life is too short to worry about these sorts of things, and I genuinely look forward to laughing at myself in the future. Don’t worry about being basic, but concern yourself about being averse to the comfort of the normal.