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.

A few years ago, the International Herald Tribune ran a story about a seismic shift in Italian fashion standards.

Some Italian companies were allowing their male employees to go tieless, and even suitless, during the summer months as a way to help fight climate change. Not requiring a tie might equate to less demand for office air conditioning, which in turn could help reduce overall demand for electricity. (More recently, Chile’s energy minister promoted the same idea.)

While probably a non-issue in the casual-fixated United States, Romans and Milanese ditching their ties at work was no small matter. Those ever so elegantly-knotted creations that men the world over vainly attempt to duplicate, gone for the summer? Well, the story made it to the IHT, didn’t it?

Though interesting from a cultural perspective, this story is an excellent argument for paying attention to what you wear, buying for quality, and focusing on real, timeless style. With Earth Day 2012 only a few hours behind us, this is a wonderful teaching moment and the lesson is this: focusing on classic style does actually help the environment – as it should.

When you buy quality clothing, you are making an investment that lasts. By quality, I don’t just mean well-made; I mean a purchase that is well thought out. When being self-aware about what you buy and thoughtfully editing your wardrobe, you are less likely to make an impulse purchase that eventually winds up in a landfill.

For the most part, clothing – whether dress or casual – is now cheap and abundant, but there is an enormous price to be paid for such mindless convenience. The environmental costs of manufacturing, transporting, storing, selling, and, eventually disposing of these cheap products are large and global.

As opposed to Americans, most Europeans tend to be more selective in their clothing choices. Due to higher prices and limited storage, each piece must be thought out and chosen for its quality, longevity, and versatility.

Does that pair of pants go with more than one outfit? Can you re-sole those shoes? Do you actually need that jacket or another shirt that’s virtually identical to your favorite one? These are the things we should always consider before pulling out the wallet.

As seen here, an Italian ditching his tie or swapping out a suit will most likely still look naturally sharp, without having to run to the department store for a new “corporate casual” wardrobe. It is probable that his wardrobe already has a purpose and a sense of continuity and relationship among its components.

Redefining how you dress is not, as they say, rocket science. But it does take some time and effort. Make deliberate choices; don’t buy cheap shoes that get thrown out when they wear out. The same holds true for tailored clothing. While often expensive, a well-made suit or custom shirt will last for years. A classically styled bespoke blazer or suit will always transcend fashion and adjustments can be made as your dimensions change.

By being selective, you can build a wardrobe that both meets your needs and reduces pointless waste and duplication. And apart from environmental considerations, when your wardrobe consists of items that fit, are well-made, and possess a timeless and stylish quality, you will wear them.

Certain brands, like Slowear, actually design their clothes to not go out of style. Slowear’s family of classically-focused labels evoke a culture of sustainable luxury. They want you purchase a pair of Incotex trousers or a Glanshirt shirt and keep them for years; sacrificing volume for long-term brand devotion. By focusing on the design and construction of their garments, Slowear is able to market what Alan Flusser refers to as “permanent style.”

Reducing your retail carbon footprint extends to accessories as well. Why cycle through five or 10 cheap to mid-grade briefcases or day bags when you could take a little time, define what it is you really want in a bag and then invest in one or two of heirloom quality?

For example, this Frank Clegg English Brief will not only never go out of style, it will become more desirable the more it gets used. It’s the type of bag everyone is always looking for and while not inexpensive, it is a solid capital investment.

Choose ties you love and that pair well with a variety of shirts and jackets. Pick up several pocket squares which can quickly add flair and personality to a tieless suit or odd jacket. Make certain style elements your signature and stick to what works with your body type, skin tone, personality and lifestyle.

That, in a nutshell, is the point of classic personal style. By making choices that take into account long-term investment and near-term benefit, building a wardrobe and curated collection of accessories reduces waste and increases value.

If nothing else, it also clears out your clutter and allows you focus on the things that truly matter. The items in your life should be those that you cherish and want to have around, they should each have a purpose and, to me at least, a story.  And when you present your best self to the world – in your dress and with your accessories – you really do tend to be a better person.