Calibrating Formality in Business Casual

If you live in a world of mostly Business Casual, it is hard to find information on how to think about your formality.  Most of the books available and the majority of the material on the web is usually focused on dressing in spheres of Smart Casual and/or Informal (see the Degrees of Formality).  There are fewer rules formulated and disseminated about dressing professionally in Business Casual.  All the same, there is a large enough range of possibilities within Business Casual to pose the risk of over- or underdressing.

So let me offer what small advice I can for properly calibrating your formality for Business Casual.  I divide Business Casual into three ranges, and below I offer some descriptions of what your peers may be wearing and what you could choose to wear among them instead without going beyond their range of formality.  While you want to stay within the basic range of what all of your peers are wearing, you can dress at the top of that range.  Before I discuss my examples for each range, let me first define the terms I will be using and give some historical background to them:

Polos.  They descend from shirts worn for playing tennis in the early 20th century (hence, some still call them tennis shirts).  Though they are as close to a t-shirt as you can get in a collared shirt, they can still look smart when well-made and fitting properly.

Jeans.  These can also look sharp when fitting well and well-constructed.  Darker jeans are more formal, lighter ones less.

Trainers.  Do yourself a favor and only wear these for playing sports.  They are not for work, dates, or other social events.  They have distinguishing marks that make them ill-suited to anything other than sports.  First, they are generally designed to look like ships from Star Wars, with busy, multidimensional designs and inorganic, clumpy shapes.  Second, they are, and very much look like they are, made of synthetic materials.  Better clothes are always made of something that once lived: wool, cotton, linen, leather, silk, etc.  Plastic, polyester, and anything else created in a lab should only ever be worn while playing or traveling to and from actual sports.

Dark Trainers.  For lack of a better name, these are basically trainers trying to pose as dress shoes by being brown or black.  They too are marred by the busy, lumpy spaceship design of trainers. If not fully plastic, they are generally made of corrected-grain leather, giving them a distinctly plastic air.  Men uncomfortable with really committing to improving their style often choose these to "dress up," feeling clever for enjoying familiar, spongy comfort in a formal disguise.  But they are not more comfortable than real shoes that fit well, and they certainly do not look professional.  They serve no purpose at all, and you never need buy any.  This is the only item in this list I am suggesting you exclude from your wardrobe.

Oxford Cloth Button Downs.  Also called Oxfords and OCBDs.  These are sports shirts made of Oxford cloth (a strong, rougher weave) featuring collars that button down.  They descend from shirts worn in England for polo in the late 19th century.  They are incredibly versatile, as you can wear them with many suits and can also wear them untucked with sleeves rolled up with shorts as JFK does in the photo far below.  These are a nice, minimal step up from polos and should not threaten others wearing polos.  Never buy them (or anything else) in a "non-iron" version.  Decent quality oxford cloth will release most wrinkles if hung up after a few minutes of warming in a dryer.  "Non-iron" clothes generally feature an artificial treatment and/or fiber that gives them an unnaturally smooth and plastic appearance.  As noted above, plastic is not the look you are going for.  You do not have to wear only Oxfords, though that is not a bad idea for the first couple of years of learning how to dress.  Stick to no or minimal pattern as you begin.

Dress Shirts. Unlike Oxfords, these feature finer, smoother weaves (like broadcloth).  These also differ from Oxfords and other sports shirts in only looking proper when ironed and worn with a coat and tie.  Dress shirts worn without a coat or tie make the wearer look they were unable to finish getting dressed.  Dress shirts also generally feature a point or spread collar, as a button-down collar is too casual for a weave like broadcloth.  It is indeed true that an ironed Oxford can serve as a dress shirt with all but the most formal suit ensembles, but while you are still learning about clothes, I suggest distinguishing between the two.

Casual Chinos.  These are a step up from jeans the way Oxfords are a step up from polos - non-threatening while improving.  All I mean by "casual" chinos is that you do not iron these and can wear them in more casual outfits.  Chinos taken straight from the drier after a few minutes and hung up to finish drying look great, albeit rather casual, with Oxfords treated the same way.  They offer what is still a non-threateningly casual look with just the tiniest bit of formality.  Again, never buy them in non-iron versions.
Pressed Chinos.  These are pressed with a crease.  Chinos do come in a variety of different weights which affects how warm or cool they are, how they look, and how they hold a crease.  You will get to know all of this in your research.

Classic Sneakers.  These suffer much less from the defects of trainers: they are mostly made with natural materials - canvas or suede (the English call them plimsolls in canvas) - and they have a much cleaner design.  They also have some history.  Generally the more your sneakers feature natural materials, clean design, and a style that has been in production since before the mid-20th century, the more authority they lend you.  Regardless, any sneakers only belong at the very bottom of Business Casual and in Private Attire.  Whenever you buy shoes, it is a good opportunity to think if you have a belt that matches their degree of formality or casualness.

Boat Shoes.  These are another classic design made of natural materials with a proven pedigree that you can wear at the very bottom of business casual.  Opt for full-grain versions.

Loafers.  These are dressier than classic sneakers and boat shoes while still being more casual than actual dress shoes with a history stretching back before WWII.  Their formality ranges from somewhat lower than to almost equal to that of Derbies (depending on the design of each).  What I am referring to here are full-grain leather loafers modeled closely on the original Bass Weejun, Alden tassel loafer, or Gucci horse-bit loafer, not the square-toed, thick-rubber-soled "loafer" made of corrected-grain leather often sold by the same companies responsible for dark trainers.

Derbies.  These are shoes that feature open throat construction as opposed to closed throat construction - Google "open throat vs closed throat shoes" for more information.  Closed throat shoes are more at home in Smart Casual and Informal, and I would also recommend reserving black shoes for more formal ensembles like town suits and evening dress.  Brown will serve you very well to begin with.  Optimally, your Derbies will be all leather: uppers, lining, and sole.  They should also have an elegant shape that is distinctly un-blob-like, and do stay away from both pointy and square toes.  Though I am suggesting Derbies for the middle and top of Business Casual, they also work higher up in Smart Casual and with the country suits of Informal.  Good Derbies are a smart investment.  Again, with each shoe purchase you should consider whether you have a belt that matches the formality of the outfits you would wear those shoes in.

Crewneck Sweaters.  If you are timid about venturing into wearing layers, these are probably the best place to start.  They hide most of a shirt and tie from view and are comfortingly reminiscent of sweatshirts.  Thus, they neutralize much dressiness.  However, that touch of linen poking out at the end of your sleeves and at the collar along with a peek at a tie knot still let out some of the power of a a tie with layers.  Stick with solids and avoid any logos or other marks.

Cardigan Sweaters.  These can serve as jacket training for your comfort level and for the eyes of those around you.  You can most easily get away with wearing one your first few times (if you have any nerves about venturing into layers) on a particularly cold day.  However, sweaters come in a range of materials from very warm wool to rather cool cotton/linen blends.  You can really wear sweaters throughout the year during all but the hottest weeks in many regions.

Casual Ties.  Solid, dark ties are quieter than boldly patterned ones.  Matte ties (i.e., not shiny) are less flashy.  Knit textures are more casual than smooth weaves.  A dark, solid, square-bottom knit tie is probably the most casual, discreet place to start.  A black knit tie will serve you for all kinds of occasions for the rest of your life.  Grenadines are another step up in formality.  Unless you are wearing something as casual as a knit tie with an Oxford, you should wear a coat or sweater when wearing a tie.  Unfortunately, some workplaces enforce a code of dress shirt and suit pants without tie or suit coat.  Perhaps they are trying to humiliate subordinates the way servants are compelled to wear liveries featuring formality-confused pairings.

Now that we are clear on the terms, let me explain how you can really dress your best in a Business Casual environment without breaking the formality barrier of the group you find yourself in.  Every group of men you will inhabit will fall into a range of formality though usually not a large one.  Feel free to dress at the top of that range, but do not go beyond it.  Here are the three ranges I would divide Business Casual into:

Bottom Range
Most of your peers wear: polos, jeans, trainers
You can wear up to: oxfords, casual chinos, boat shoes or classic sneakers

Middle Range
Most of your peers wear: polos or sports shirts, chinos, dark trainers
You can wear up to: oxfords, chinos (perhaps pressed), derbies or loafers, crewneck sweaters

Top Range
Most of your peers wear: sports or dress shirts, ties, chinos, dark trainers or derbies
You can wear up to: dress shirts, ties, pressed chinos, derbies or loafers, cardigan sweaters

(click to enlarge)
If your peers wear what I describe for them at the bottom of Business Casual: polos, jeans, and trainers, you would be too out of step to wear what I suggest for you at the top: dress shirts, ties, pressed chinos, derbies or loafers, and sweaters.  It is generally safe to dress a shade or two more formally, but not much more.

Your task is always to figure out the formality range of any occasion and to wear what will make you look best within it, which can usually mean dressing at the top of it.  As you encounter different outfits when you visit the links offered below, read the suggested titles and watch the movies I recommend, always think of what could be appropriate to the occasions of your actual life.  You can learn to dress very well in in any occasion without ever over- or under-dressing.

Should your work or leisure peers only wear t-shirts with shorts or jeans, they are stuck in Private Attire and this limits your choices considerably.  You could probably get away with the bottom range of Business Casual around them, but I would not suggest pushing any further than that.  Wearing a coat and tie to a BBQ where your friends are in shorts and flip-flops is never a good idea, though taking your special lady out and dressing for a restaurant where men wear coats and ties is.  You can be ambitious without making your friends uncomfortable.  Do not force your clothes onto your social spheres, use your clothes to fit into and enhance them.  If you do not like your options, then you need to move into spheres that give you more possibilities.  To paraphrase Nilsson, you need to go where the weather suits your clothes.

Once your Business Casual wardrobe is established, an easy way to convert it into a very basic Smart Casual wardrobe is to add a navy blazer and/or a brown or grey tweed sports coat.  If you want pants up a step from dress chinos, try a pair of grey flannels.

Here are some classic examples of Business Casual starting off with one of JFK dipping below Business Casual into Private Attire to demonstrate the versatility of Oxfords:
Patrician Private Attire:
rolled up, untucked Oxford and cotton shorts
Untucked Polo and Chinos
Polo, Chinos, and Plimsolls
Polo, Chinos, and Suede Derbies

Tucked, Rolled Oxford and Chinos

Oxford and Flannels
Crewneck and Chinos
Crewneck and Chinos

Harrington Jacket, V-Neck, and Oxford
Cardigan, Oxford, Chinos and Suede Derbies

As Casual as Possible Oxford with Casual Knit Tie
Cardigan, Oxford, and Knit Tie

Publications to Read


Conservative Primers with Many Pictures:

These will help you understand the most stable conventions and traditions in menswear with plentiful pictures to help you instantly visualize what is discussed.

Dressing the Man, Alan Flusser
Gentleman: A Timeless Guide to Fashion, Bernhard Roetzel

Trendier Publications:
On newsstands twice a year (fall and spring), these will help you know what is in style for the current season, knowledge you should combine with the information from the more conservative books.

Esquire: Big Black Book

GQ Style: What to Wear Now


Conservative Books with Few or No Pictures:
Though very informative, these are best read once you are very familiar with the names of the various garments of men's style - or with the internet in front of you to search for images - as there are not enough pictures to help you visualize what is being discussed. They will help you understand further traditional guidelines, standards of taste, and origins of conventions in men's style.

Elegance: A Guide to Quality in Menswear, G. Bruce Boyer
The Suit: A Machiavellian Approach to Men's Style, Nicholas Antongiavanni

Though including many helpful images, the first is very text heavy, giving a wealth of detail on historical development. The second book is mostly just images.

American Menswear: From the Civil War to the Twenty-First Century, Daniel Delis Hill
One Hundred Years of Menswear, Cally Blackman

For further suggestions, consult Gentleman's Gazette's list of 100 Books.

Comments and Questions Welcome