The Curse of Smart Casual

A few weeks ago, a reader posed what turned out to be a somewhat complicated question; “what do I wear,” he asked, “to a wedding where the dress code is “smart casual”?

In most cases, a wedding is one of those events that are fairly easy to dress for. In the summer, a well tailored poplin or linen suit should fit the bill. Depending on regional preferences, perhaps seersucker or, as was the case for my wedding, white ducks and a blue blazer. For formal events, a morning suit or white dinner jacket is best for daytime and of course a dark colored dinner jacket is always correct for an evening wedding. (Try midnight blue instead of black for some real style)

Personally, I have a rule when inviting others to an event of mine; either I tell my guests in detail what they should wear or I don’t tell them at all. Why, for an occasion as important as a wedding, would the host offer such an ambiguous sartorial instruction as “smart casual” – especially when doing so throws a wrench into an understood social convention? Why do otherwise reasonable people do such frustrating things?

My own theory is that we all want to be creative and different at important moments in our lives. We want to stand out from the pack and be recalled as creative. That’s all well and good, but it only works when everyone is included in the plan.

Several years ago some friend of ours decided to throw a surprise wedding – they wanted to be unconventional, so instead of wedding invitations they sent out invitations to an open house. They had just moved to a lovely mountainside location, so it made sense to those receiving the invitation. The problem was that we live on the other side of the country and flying out for an afternoon open house would have been expensive and difficult, so we declined. This couple was so intent on keeping the true event a surprise that they never let us know what we were really missing – not even a hint. It took a while to get over that one.

My point is that unless everyone is on the same page, you are putting an undue burden on your guests to figure out what’s going on. Had we known the truth, we would have been on the next plane. To a lesser extent, cryptic phrases like “smart casual,” “summer festive” or worse, “beachy fun” leave the wedding guest in a bind. To one person, smart casual may mean tailored chinos and polo shirt while to another it might be an elegant suit with no tie but a nice pocket square. And what the heck is beachy fun – should I wear swim trunks?

In this case my reader knew the groom’s personality and that his likely attire would be a suit and tie. The groom’s only additional direction was that he and his fiancé wanted people to be “comfortable.” Though intended to be helpful, this additional nugget of information only served to make things more confusing.

My approach to this unfortunately vague scenario is to go classically simple. A nice sport coat, open collared shirt, pressed trousers and polished shoes will get you through almost any situation. Blue blazers in particular earn their keep and, because of their inherent versatility, can handle dressy and casual scenarios with aplomb.

All in all, when faced with situations such as these it’s best to sit back and take a deep breath. If you are not able to or comfortable with asking your hosts for some specific direction, take the middle route. Try not to over dress, but for goodness sake do not under dress.

One Thing: The Polo Shirt

Polo shirts are the cornerstone of any classic warm weather wardrobe and have been so for generations. Though when they hear “polo” shirt most people think Polo™ shirt, the first truly branded version was developed in 1929 for tennis legend Rene’ “The Alligator” Lacoste.

Lacoste wanted a comfortable shirt to replace the traditional, but totally impractical dress shirt and tie worn by tennis players at the time. In doing so, he unwittingly produced one of the most versatile warm weather shirts ever. Whether tagged with a little reptile or tiny horseman, the polo shirt belongs in your summer rotation.

I would suggest that the polo shirt is in fact one of the great sartorial innovations of the last few generations. With its unique ability to straddle the elusive line between casual and formal, the classic polo can carry you from the office to the country club with little stress. In today’s corporate casual world, day to day office wear can be a challenge and while I do not suggest that a knit polo shirt is right for every occasion, when paired with a sharp outfit you should be good to go.

Khakis are a traditional choice and usually fine for most situations. Just ensure that you do not pull on the going-to-pick-up-a-can-of-paint pants. Opt for a nice pair of khakis in fine cotton – the ones constructed like dress pants. Keep it less stuffy with clean boat shoes or penny loafers and a woven leather or ribbon belt.

For a more business feel, try a dressy belt with a silver monogrammed buckle, blue blazer and high grade slip-ins from Ben Silver. I’ve even seen a black polo paired with a pinstriped suit; very sharp in a George Clooney sort of way. Be careful with that one, not many men can actually pull it off.

Whatever look you’re trying to achieve, make sure to follow these simple guidelines to always be your best when sporting a polo shirt this summer. First, as always, ensure that the fit is right.

Avoid going too baggy, an annoying sin of the younger set. A trim fit across the shoulders – so the shirt’s shoulder seams actually land on your shoulder – should be your first goal. You don’t want any pulling or bunching, just a natural and comfortable fit.  The body of the shirt should lightly touch yours, but not pull or feel tight.

The sleeve should hit around mid-bicep and be fitted but not constricting. When un-tucked, your shirt should hang no lower than your hips. In no case should it cover your rear like some kind of mini skirt; that never looks good.

Regardless of how well it fits, when in the office, keep your shirt tucked in.

Even when you’re going for a younger look, say with modern jeans and some vintage shoes, a trim fit will keep everything looking fresh. Many designers have come out with slimmer fitting polo shirts, so make sure you try on several brands and see what feels best. And trim does not mean tight – unless you want it tight of course, which is another look altogether.

In my case Ralph Lauren shirts fit very well. The body, arms and length are just right. Still, I pine for a Lacoste polo but the cut is just too way slim for my build. I also have several Brooks Brothers shirts and they fit me well, but not as well as the Polo polos.

One of the best things about these versatile shirts is that they come in almost any color under the sun. Basic white to jet black; solid color or preppy stripe, you can find it.

They also happen to age very well. That really beat up old polo at the bottom of the shirt drawer - the one with the seriously frayed collar? It will look great at the clam bake with some faded khaki shorts and gin & tonic.

To Cuff or Not to Cuff

The other day, I had an interesting question posed to me by one of my readers. He had recently purchased a pair of pleated trousers at Brooks Brothers and it was recommended that he have them hemmed with cuffs.

His wife, who is German, objected to this approach and cited her and her European friends’ opinion that stylish men do not cuff their pants. In a quandary, he called up the store and talked to another associate who said that pleated trousers demand cuffs and that their added weight help the pant leg hang properly.

Unsure if this were the best advice, my reader asked the same question of me. I understand the confusion because this tricky issue that is one that’s both sartorial and personal. By that I mean the question of cuffing one’s trousers is partially based on a cultural perspective and partially on personal taste.

For starters, his wife is correct that in Europe cuffed trousers are less common. The fact that his wife is German certainly explains her dislike of cuffs. The German aesthetic, when it comes to function over form and elegant austerity over lively embellishment, is fairly well known.

Across Europe though, as with anywhere else, fashion preferences change. I purchased a pair of wonderful Incotex pants in Venice and had them tailored there as well. The salesman and tailor both recommended cuffs, the execution of which had some of the most beautiful finishing work I’d ever seen.

That these immensely stylish and opinionated Italians recommended cuffs caught me off guard because the pants were in fact, flat fronted. Flat front trousers are pretty much the rule in Europe and I began to think that to my reader’s wife, therein lay the real issue.

I suspect that she wants her husband to embrace a more Eurocentric wardrobe, sans the pleated trousers. Generally speaking, pleated trousers are far more common in the United States than in Europe. The only caveat to this generalization is England, where you’ll still see pleats a little more often than elsewhere on the Continent. It’s also still fairly normal to see pleats on both American and English suit pants.

Anyway, to get back to the original question; when it comes to tailoring, pleated trousers should always have cuffs, period. The weight of the cuff will help the trouser leg hang and both physically and visually balance the peats up top. On flat front pants it’s more of an option dictated by personal preference.

For example, my Incotex trousers are a very fine gray worsted and the cuff help keep the lighter fabric from riding up my calf. Also, since Italians like their pants legs cut so darn high (barely touching the top of the shoe) you need that weight to keep them in place. Had wished to do so, it would have been perfectly acceptable to have gone with no cuff and have the hem cut longer.

So, here is where it all comes together: if you like pleated trousers, they really need to be cuffed. If you’re working with flat front trousers than it’s a preference thing and either option is just fine.

Another way to look at it is from a cultural perspective. Pleated and cuffed trousers just look American, especially with the fuller cuts favored by American brands like Brook Brothers. That’s not a bad thing, it’s just a truth. How do you want to look; American or European?

Personally, I tend to like classic American casual clothing and European tailored clothing. When I go to Europe, I try to dress less American; not for any political or self-conscious reasons, I just enjoy the change.

My ultimate recommendation is always to go with what you like and what feels right, because in the end you’re the one wearing the clothes. Still, as someone with a wife who has a killer eye for menswear, I never discount what she has to say.

My Father’s Shoes

As a young child, I remember sitting in my parent’s room, watching my dad get ready for the day.

As a physician, and one who felt that dressing well shows respect for others, he almost never went to the office in anything but a coat and tie – often a suit, sometimes a sport coat and gray flannels.

I would sit and watch as he picked out his clothes, running his hand along the ever growing collection of repp, paisley and woven ties until he found just the right one for that day.

After the jackets, shirts and ties had been sorted through, out came the shoes. Dad’s shoes were not handmade or exotic. They were however solid footwear of very good pedigree: Johnston and Murphy (the good line), Brooks Brother’s Peal & Co., and Barrie, Ltd., of New Haven (sadly, now defunct).

It still amazes me that for someone who wore dress shoes almost every day of his life, his footwear wardrobe was not particularly large. As I recall, he had a pair of each of wing tips and cap toes – black and brown; a lovely pair of shell cordovan brogues, brown tasseled slip-ins; a pair of penny loafers and a pair of white bucks.

Dad always kept his shoes in excellent condition; religiously polishing them to a deep, jewel like gloss. Of course each pair had its own cedar shoe trees – if you don’t have them for your shoes, stop reading now and go buy some. The sense of personal satisfaction I still get from shining my shoes, looking after my wardrobe and getting the closet in order after a busy week was surely instilled at that young age. There is a certain rhythm and comfort in the ceremony of assembling your personal possessions.

What actually brought these memories back to me was the never-ending rain that blanketed Washington earlier this week. Normally when the weather turns like that I dress down a bit and wear some heavy shoes and khakis, but I had meetings this week and needed to wear a suit.

Since I metro into the city and would be exposed to the elements for more than enough time needed to soak through shoe leather, this was an issue. I found my solution in the most practical of footwear accessories – rubber shoe covers. These waterproof shoe covers turn your well shod feet into pedial all terrain vehicles.

I never actually thought that I would own a pair of these things; they were to me about as un-cool as you could get. I still see my dad pulling them on before he walked out the door on rainy mornings and recall how, in my youthful ignorance, I thought he looked silly. As a working adult however – and one who enjoys assembling a good wardrobe in the morning – I know now how invaluable they truly are.

Taking care of your shoes does not always have to be an elaborate or overcomplicated exercise. Keep the soles in good condition, give them a regular polish and each pair should have their own shoe trees. And, as my dad taught me a long time ago, keep them dry.

Visiting in Horse Country

My wife and I recently took a little vacation to the heart of Virginia horse country. Middleburg, ground zero for the moneyed portion of Virginia’s horsey set, is exactly what you expect an exclusive equestrian hamlet to be. With beautiful rolling green hills, dotted with heart-stopping estates and crisscrossed with white fencing, it easily evokes visions of Ralph Lauren ads.

We stayed at a wonderful country estate named the Goodstone Inn. I say estate because that’s really what it is. Set on 265 acres, the Inn is an award winning collection of residences, barns and stables spread across the property. There are actually five buildings in which to stay, each with its own distinct theme. The original carriage house serves as the Inn’s living room and also houses their exceptional restaurant.

If you happen to be in the DC area, make sure to stop by for a few days; it is a different, more genteel and refreshing world. A warning though; you’ll quickly want to become the landed gentry.

In fact, visiting horse country often inspires one to dream of misty morning walks to the stable and a rambling family house stocked with giant oil paintings, antiques and sterling silver knick knacks. You might also feel a strong desire to ditch your current wardrobe for something more earthy - heavy on the leather and waxed cotton.

The storied anglophiliac horse culture of Maryland and Virginia can easily bring these feelings to the surface in almost anyone. But before you go galloping off after crafty foxes (or, nowadays, pre laid artificial fox scent trails), you’ll need to look the part.

Dressing for this kind of an environment is a balancing act because good horse country style is really a blend of bespoke and stable boy. One of the best suggestions I heard for getting the right mix came from a local: think of Prince Charles, then put him in a pair of jeans. Not 7 For All Mankind or anything like that, just plain old jeans.

And that really is the style guide I would suggest. Most of the Middleburg horsey set is very well off – horses are not really a poor man’s accessory – and they revel in their earthy, down home English/American lifestyle.

When we visited, it was transition weather; warming days and cool evenings. Barbour jackets, sans liners, and leather paddock boots tended to form the core of many folk’s ensembles. Jeans or trim khakis, paired with simple merino or cotton sweaters or well tailored shirts, added to the dressy casual vibe.

Most of the people I saw had on clothing that looked nice but not necessarily new. To me this was very refreshing and appeased my New England aesthetic for worn-in classics over of-the-moment flash. Several of the women I saw around town were wearing jodhpurs and lovely riding boots; just back from an afternoon cantor I guess. The men were more Ralph Lauren-ish, but in a practical way. They often looked as though their clothing was tossed on without thinking, but from a wardrobe that had only great clothes in it. I think we all need a good hacking jacket in the closet.

That’s a good lesson for all of us; if you only choose things that are of high quality, great style and good material, your wardrobe should always yield a great outfit for any occasion. I recall one gentleman who had on a slightly muddy pink hacking jacket, white cotton oxford, old jeans and barn boots.

Stepping out of a dark green Range Rover he looked elegant and natural, not at all contrived. I think that’s a personal goal most of us aspire to.