Besides making the decision to start dressing better than average and acquiring the various skills and items to make that possible, average guys with more than a passing interest in kicking up their everyday style several notches need to develop a particular mindset when it comes to dressing nicely.
"Dressing nicely" might come across as a somewhat arbitrary and subjective concept, so let's clear the air and define our terms before continuing further. What I mean by "dressing nicely" is when a man presents himself in such a way that he come across as having a bit of polish and sophistication behind him. More directly, he ain't coarse. Naturally, a guy doesn't have to come from a privileged background to be polished and sophisticated either. It is entirely possible, and even desirable, for a guy to make a concerted effort to improve himself, learn the ropes, and become well-versed in how best to present himself. A bit of personal upward mobility is key in all of this however.
Right. With that out of the way, let's consider the mindset of dressing nicely. Off the top of my head, there are at least eight things for a guy to consider and keep in mind as he makes the sartorial journey from clueless slob to polished sophisticate:
1) Develop an awareness of how good a guy can look when he is really dressed.
You don't have to walk around looking like you just rolled out from beneath a pile of stinky, dirty, wrinkled laundry. Open your eyes a little and look around you. Start noticing the men who tend to dress batter than average. They really do exist, you just have to look for them. Start noting how these guys do it, and what sets them apart. Ask yourself what might work best, and, conversely, what doesn't quite do it. Is it how they combine colors and patterns? Is it how their clothing fits them? Or is it a clean, uncluttered, almost sombre and yet elegant look? What kinds of shoes do they combine with what clothing combinations? What are their manners and behavior like? How do they conduct themselves with others? Pay attention to details like these and imagine how you might do it yourself. Because you are, or are about to.
2) Cultivate deep curiosity about classic men's attire.
Learn about what's out there, how men (at least some of them) dressed in the past, and how you can improve your own daily look ten-fold in the present. In other words, read widely, but don't limit yourself solely to authors like Alan Flusser, Bruce Boyer, or Bernhard Roetzel alone. There is actually lots of relevant, albeit low-key, material on classic attire to be found on the 'net these days too, but you have to find it and sift out the more garish, trendy I-gent chaff.
3) Maintain a whimsical sense of humor.
Others might rib you occasionally about your attire and, perhaps, make fun once in a while. So, it's a good idea if you learn to laugh along at yourself and maintain a sense of humor about working to kick up your everyday style several notches above that of most guys in 2014. Keep your sense of fun and don't let things get too heavy in your sartorial journey. Besides, if others see that you don't take yourself too seriously, it becomes less interesting to razz you about your gear.
4) Be willing to experiment and try new things.
Don't let the idea of color, texture, and pattern scare you off. The world of classic men's attire is more than simply grey, navy, or black. What about houndstooth, herring bone, chalk stripe, and plaids? The point is to maintain an open mind and be willing to try new and different things once you've made up your mind to start dressing better than is now required of most men in most walks of life. Realize that some days you'll nail it, and other days you won't quite get there with a particular combination. No matter. The fun comes in trying and learning what works best for you.
5) Learn to recognize what works. . . and what doesn't.
As suggested above, do your homework here and read up a bit on classic male attire to learn what it is, what it most definitely is not, what kinds of clothes are appropriate for certain situations, and how you might put together various ensembles for various occasions. Much like professional musicians develop their ears through practice, a guy interested in kicking up his everyday style should make the effort to train his eye through both reading and examining illustrations and actual photographs of men wearing classic attire. But steer clear, by all means, of the übertrendy online "mimbos," invariably in jackets and suits that are too sort and too tight, which abound in the 'net. Physical publications like GQ and Esquire also feature too many guys dressed like this, so best to cancel your subscriptions, or simply let them run out.
6) Maintain the sartorial precedent set in your family.
If dear ol' Dad, or another male family member, set an example for you at a young age by dressing well for work and (possibly) at home, or at least better than average, your own internal journey to dressing better than average becomes easier. There is no psychological baggage to lose, or chains to break free of, before you can allow yourself to jettison certain habits and, perhaps, also negative attitudes about dressing nicely.
7) Get a set of brass cajones.
No explanation necessary, but it helps if you've got some chutzpah (self-confidence in other words), so that you don't feel and therefore appear self-conscious and uncomfortable in those newly acquired clothes. The easiest way to get that self-confidence, if you don't have a bit of it already, is to wear your clothes. Put 'em on, wear them most of the time, and make 'em part of your usual scenery. If you see yourself dressed in, and other see you wearing, nicer clothing and shoes all of the time, they stand out less over time and draw less attention. You forget they are there, and your clothes become simply an extension of you.
8) Stay focused and steer the course.
Don't deviate from your aims and remain firm in your resolve to dress and act better than has become the sad, accepted norm in many (most?) places. Not everyone will necessarily get it or appreciate your efforts though. Be aware of that from the start. Some might even be openly hostile, in one way or another for one reason or another, but don't let that put you off. See my previous point and continue to cultivate better dress, more polished behavior, and urbane interests and attitudes. The "civilized" world needs more of all four in 2014. Oh, yeah!
To my mind, that's the mindset a guy needs to turn things around and kick up his everyday style several notches where clothing and personal habits are concerned. As always, I'm interested in your comments and opinions, but let's keep it clean, please.