When speaking of the most basic levels of competence, an oft-invoked benchmark involves one’s ability to dress one’s self. An example: “I’m not sure if I would trust Ernie with that new account…he knows how to dress himself, but this might be a little above his pay grade.” When viewed literally, the adage makes perfect sense. What, after all, could be more simple than covering one’s naked flesh before heading out the door? What is one of the first things we learn to do independent of our mothers and fathers, alongside using the toilet and brushing our teeth?
When considered in full, the words are misleading. Dressing one’s self, in the most bare-bones sense of the phrase, may come easy, but dressing one’s self well remains a bit more elusive. Nowhere is this truer than in the realm of casual men’s dress.
A common mistake, and one that I made myself until very recently, is to assume that dressing “casually” is synonymous with dressing sloppy. While the rules of style relax and loosen further down the chain of formality, to assume that casual dress works in spite of thoughtlessness is an egregious, though all too prevalent error. Visit any college town or urban center where tourists congregate, and you can see the proof in all its gaudy glory: branded, ill-fitting t-shirts and crocs as far as the eye can see.
In the world of style, as in most other spheres, men have it fairly easy. The uniform basics of men’s dress allow for a much more minimalist and pared-down closet, and men’s pieces tend to last longer and sell for less. However, the hard and fast rules and variable conformity of tailored style often leaves some men in the dark when the time comes to hang up the monkey-suit and step out a little more. It’s like a teenager who has been wearing a uniform to school his entire adolescence suddenly being told that he can wear whatever he wants; the results will always be interesting, but usually the apparent evaporation of rules and authority will lead to some very suspect decisions.
This is the root of the problem: many of the rules for more formal dress still apply to casual wear, and dressing down has some of its own unique rules as well. As mentioned earlier, you can play faster and looser the more casual you get, but throwing caution to the wind means you’ll end up looking effortlessly sloppy, or worse, like a study in failure. To reiterate, nobody is asking you to put a ton of thought into what you’re going to wear while you mow the lawn or head to the gym, but you might want to look like you give a shit if you’re headed to a first date or meeting some folks for a day-drink.
As with dressier occasions, fit rules the day. If your clothes don’t fit properly they’ll make you look dumpy and sloppy, and give your body a blobby, amorphous shape. The reason so many guys run into trouble with casual fit is that not many people bother to tailor casual clothes. This attitude is understandable: a dress shirt or a suit jacket seems like something appropriate for a visit to a tailor, and something that you’re just going to wear out with buddies doesn’t. Part of it may be a fear of appearing too try-hard, but most of the time, it takes effort to appear effortless. In my personal opinion, a fit that is as close as possible to the natural contours of your body without being constricting is optimal. A lot of guys who are bigger or smaller than average will mistakenly think that loose or baggy clothing will improve the perception of their physique, but clothing that doesn’t follow the natural lines of your body makes for an ugly and shapeless silhouette, which usually does little else besides highlight your worst attributes. Be proud of what you have going on, and dress accordingly rather than trying to hide it.
While there’s certainly more room for experimentation and improvisation in a casual outfit, generally speaking, it’s best to have a uniform aesthetic. This doesn’t mean that you need to go full on brand-whore and stock your closet full of nothing but Polo and Brooks Brothers, but it does mean that you run the risk of having your sartorial message garbled when you mix and match disparate items too much. This can get very subjective, but use your best judgment. Big chunky work boots will look a little out of place with pastel-colored shorts, for example. Same goes for a t-shirt with gray flannel trousers.
Above all, you should be comfortable. This will be aided by wearing clothes that fit, but comfort is as much about your state of mind as it is about whether or not anything is pulling or bunching. If you’re on edge because you feel like that Supreme hat looks stupid on you, go without. If you just can’t get into the drop-crotch pants fad (this seems to have mostly died out, thankfully) then leave it on the cutting room floor.
Remember, nothing I or anybody else says should be taken as gospel truth, but in my humble opinion, timeless classics always age well, and it’s hard to screw up something that’s beautiful in its simplicity.