On Dressing Well

Thinking about what you wear and why you wear it can lead to the question, “Why dress well?” I “dress well” because my attire suits my personality and by putting together outfits that just seem to “work.”  I think that clothing matters, but mostly as a reflection of style.  Why do I dress the way I do?  Why do I think it matters?

Photo by Jacob Slaton

Photo by Jacob Slaton

Why Dress Well?

A common distinction to make is that “style” relates to your personal collection of looks and dressing preferences while “fashion” refers to those shifting fads that come and go.  “Style is personal, fashion is temporary” is another way you may see that.  Some looks are called timeless because they have a style to them that transcends the fashion of the moment.  The idea that you can have a personal style, and not just a sheath of clothing is where we need to start.  What I am talking about here is style, not fashion.

Dandy 1

First, because style reflects a personal set of choices, it is important to be comfortable with who you are both physically and mentally. The most important thing to begin with is to know yourself.  Physically, you have to be honest about your size and your shape.  Some clothes look better on some frames more so than others; it does no good for you to lie to yourself about it.  Despite the images in popular culture, a double breasted suit looks better on a trim individual than a broad individual. We’ll get to the “why” of that later, but admit to your own imperfections so you can dress well. Mentally, you need to know who you are and who you are comfortable being.  My personal style is a more formal style, with a lot of suits and ties, because those reflect who I am better than jeans and a t-shirt, but I always keep a flash of something dissonant.  I have a bit of a dandy in me, so the socks are often wild, the lapel sports a flower, or my belt seems just ever so out of place. That slightly out of the normal component is part of who I am. The oft-mentioned “confidence” as the basis for looking good is rooted here – when you are honest about who you are the confidence in whatever you wear will appear.

Dandy 2

Second, we acknowledge that our appearance matters.  I know that there is a utopia we seek where we are judged entirely on who we are absent any appearance involvement.  That utopia does not exist.  Our appearance matters because it will shape how others see us, even if only for the first impression,.  This is a powerful thing and if you are comfortable in who you are, you will be comfortable with this part of the process.  In sociology and social psychology, there is a concept called “idiosyncratic credit” which, roughly stated, the more you appear to be within a certain set of norms, the more you can later deviate from them.  An example of this would be that, because I wear suits and “dress up” as often as I do, the flourishes I add to those outfits that are outside the norms are accepted. If you are in a professional field, wearing suits and ties is almost required just as part of the norm of the culture.  If you are in a creative field, you may find that a suit and tie is the deviation and you are not respected as much as if you were more “dressed down.” One reason that I dress well is that I do know others will judge me on my attire, so I choose to put the best foot forward that I can.

Layering 2

Third, we acknowledge that our personal style will reflect to others what we want them to see.  The sum of the first two points about dressing well is this point.  By choose our personal style to reflect who we are, and knowing that our appearance will matter to others, we can shape how we are perceived.


Fourth, it feels good.  When you feel like your outside reflects your inside, it just feels good.  When you wear clothes that fit, it just feels good.  I admit that I do stand out a lot of times because I tend to be “overdressed” but I would rather that than be “underdressed.” I like how my outfits make me look and I like how they present me to the world.

How to Dress Well?

Menswear, especially business and formal menswear, is all about proportions. The not-so-secret part of men is that clothes are about their proportion to your body.  Have you ever seen a broad-shouldered and barrel-chested gentleman try to rock a 1″ skinny lapel suit?  It doesn’t look “right.” Conversely, a fat 3″ wide tie on a lithe gentleman looks somehow wrong as well.  These are not playing to the proportions of their body.  Think about it for a few seconds – The deep “V” of a classic two button suit bisects a man’s height, but the “V” itself makes him look taller and have broader shoulders.  Hats look better when they are in proportion to your head and shoulders.  It isn’t nearly as hard as it seems to put together a good outfit when you realize you are dressing your own body and how to use those proportions to your advantage.

Great Photo by Mark Pace; badly fitting sit

Great Photo by Mark Pace; badly fitting suit

Here also the fit comes into play.  Because of the proportional nature of the clothes, when you wear baggy or oversized pieces, it throws that proportion off.  A wider gentleman, uncomfortable with his particular shape, may try to disguise that with a looser fitting suit or jacket – the problem is that this only makes him look even wider than he already is.  If you are not happy with your size or shape, you can certainly make changes to your life to change those things, but don’t underestimate the power of your attire to help you feel confident with where you are right now. Wearing clothes to fit the body you have will make you look sharper, even in jeans and a polo, than ill-fitting clothes.


Menswear doesn’t have to be expensive. Yes, it is frighteningly easy to find expensive examples of menswear and the style or fashion based media does a wonderful job of promoting pieces that are, frankly, outside of most of our budgets.  You don’t have to start there, though.  Staples and basic pieces that you can wear as part of a wardrobe are easy to come by in affordable versions.  No, the Target white button-down shirt will not be as a high a quality as the Brooks Brothers shirt, but if you wear it well that will hardly matter.


Nor does your wardrobe need to be expansive.  While I am not a fan of wearing the exact same thing everyday, a curated wardrobe of pieces that all go together can exist.  Knowing what your professional attire should be and how you prefer to live your off-work hours will let you pair down your wardrobe. I’ve been winnowing t-shirts for quite a while now because I just don’t wear them that often.  I like wearing suits, so I expanded my suit collection. No one mix of clothes is exactly right for everybody.

Dressing well isn’t about finding the most expensive articles of clothing to wear in slavish devotion to the latest magazine spread.  Dressing well is about coming to a place where you know who you are, who you want to be, and who you want others to see you as.  It is about making simple choices and wearing clothes that fit, physically and mentally, your life.