How to Dress Well

A reader recently posed to us an interesting question that gets at the heart of dressing well: does it matter what you wear when no one is looking?

This gentleman has the benefit of often working from home, and when not there, is frequently on the road. When working from his home office, our friend’s work wardrobe barely moves beyond college tee shirts and old shorts, or on a chilly day, jeans. On the road he has a few suits that he says do little for him on the style front. And while he does want to project a polished image, his main complaint is that he does not know how to come across as a professional without a suit.

He sees donning a suit as an obligation based on his audience for the day, but does not know how to “modulate” his work wardrobe to allow for some other options that let him express some personal creativity and style. For starters, a suit is by no means the only “dress up” thing in a man’s wardrobe.

Too often, men see dressing well as a chore, something to avoid, or something against which to fight.

For some it’s a latent fear of dandyism. Other times, it is a misguided sense of self-righteousness; a feeling that you’re fighting conformity, not buying into the “suit” thing – you know, being more real.

That philosophy usually ascribes that one simply conform to a different model of “conformity.” Dressing like a perpetual college student in order to make a statement is very much its own model of conformity.  As the fellow in the picture above clearly demonstrates, flair, panache, and confidence know no age.  His comfortable dapper outfit would look equally at home on a man half his age.  Alas, too many men half his age would not have the confidence to step out so well attired.

Dressing for Yourself & Others
There is a world of style and personality between flip flops and a three piece suit. Rolling out of bed and shuffling down the hall to check the email is not the point here. However, when you step out of the house or log onto a video conference, there is a certain social contract into which we enter. What you have on now matters. Once you start interacting with other people in you ought to show them the same level social and sartorial respect you yourself would expect in return. You should make an effort to dress well because you want to.

The first rule in dressing well is that you should always be comfortable and true to yourself. The second rule is the equally important fact that whether you like it or not, people judge you by how you dress, how you carry yourself and treat others, your social skills, how you speak, etc. Research has repeatedly shown that on average, it takes about eight seconds for an individual to decide what kind of person you are and it can take years to alter that initial perception. How you react to this universal truth is your choice.  This means creating appropriate wardrobes that reflect your sense of self, but which are appropriate for the situation in which you find yourself.

Clothing is one our most obvious and influential social markers. How you choose to dress directly impacts what people think about you and, often what you think about yourself. Radical changes are not always necessary; getting new jeans in a darker wash that fit well or buying some new dress shirts that work with or without a tie take make a huge difference in how the world sees you.

In our reader’s case, we suggested updating some of his separates as it turns out he does not have to wear only a suit when he travels for business. A new blue blazer and a couple of sport coats, new shirts that actually fit, and new flat front dress pants significantly updated his professional appearance. Having everything properly fitted and tailored cost a bit up front, but he told us afterwards that how he sees himself has changed dramatically.

Fit & Quality
If you choose or are obligated to wear a suit every day than take the time to learn what makes a great suit great. Pay for quality, fit, and construction.  It’s often more than you might prefer, but these things are the sartorial equivalent of a capital investment. And never forget that fit is what matters the most; for suit coats, sport coats, or blazers, this means shoulders. A properly fitted shoulder is the foundation of a jacket that properly fits its wearer. After that, the overall proportions will vary by individual body type and preference. Learn what you like: fitted and trim or loose and flowing, shorter or longer jacket skirts, one or two vents, two or three buttons (or double-breasted). Do you prefer a more European armhole that sits tighter to the shoulder or something less fitted?  Natural or structured shoulders?

The same type of rule holds true for trousers. If the fit is wrong, nothing else really matters. Do you prefer pleats or flat fronted trousers, full break or no break on the pant legs, what kind of rise? Trousers should always be comfortable whether sitting, standing, or moving.

Your dress shirts should flatter your physique, not envelope it with yards of fabric – or strain at the buttons. The neck should allow for two fingers to comfortably slip inside the collar when buttoned, shoulder seams should sit on your shoulders as would your jacket’s, and sleeves should generally end at or just below your wrist bone.  Take into account how much shirt cuff you want to show under your like your jacket’s sleeve – some should be visible.

Take time to try different fits and styles of clothing that flatter and are comfortable to and on you. If you wear business casual all the time, make the effort to expand your wardrobe. Instead of polos and khakis five days a week, add in some nice tailored pants and dressier casual shirts. Pick up a variety of sport coats and have them properly tailored. Making even these simple changes help to create a more flexible and professional wardrobe.

If, like our reader, you work from home and have client or co-worker meetings less often, keep abreast of general style trends. Update your wardrobe selectively and make sure to have someone else give you an honest assessment about color, fit, and style.

Pay attention to how you look when others aren’t around so that when they are, you always present your best face.


Be Sociable, Share!


  1. Don

    Excellent advice for all of us, not just the younger man starting out in life.

    But for you younger men: When you have your suitcoats or sportcoats altered, ninety-five times out of a hundred the fitter will want to have the sleeves extend down to your knuckles. You must insist on getting the proper sleeve length. Be firm, and don’t be surprised if you get into an argument over it. I had one tailor tell me, “all the men wear their sleeves this long.” Well then, all the men are wrong. I went to a different tailor.

  2. Thanks very much Don. I agree completely with your observation about tailoring and sleeve length. I cannot count how many times I have seen suit jacket sleeves literally envelope some guy’s hand. It’s not cool or modern, it’s sloppy.

  3. Frank

    “For some it’s a latent fear of dandyism.”

    A dandy, by definition, is “a man who gives exaggerated attention to personal appearance” (Miriam-Webster), “a man who is excessively concerned about his clothes and appearance” ( or placing “particular importance upon physical appearance, refined language, and leisurely hobbies, pursued with the appearance of nonchalance in a cult of Self” (Wikipedia).

    I’ve been called a dandy; it’s offensive. Being attentive to one’s looks is not the same as being vain.

  4. Mr. Lung, in answer to both of your queries, I neither swiped nor lifted Scott’s image.

    It is very much a photo from And, if you roll over the image you might notice that the photo’s name is unchanged and I have added a “via Sartorialist” attribution for those interested in the image’s provenance.

  5. stephen

    Good post..agree with all…and great picture!

    Old guys playing tennis, and old guys dressing well…
    Those things make me happy. They both signal “I love being alive”

Comments are closed.