3 Random Sartorial Mistakes That Bother Me
As we head into this holiday season, with shopping and gifts on the near horizon, I want to point out a few pet peeves of mine. They are simple areas of improvement that can benefit guys everywhere. Not major investments, they are more simple behavioral changes; minor yet still egregious sartorial errors that people make on an all too regular basis. So, before you get that fancy overcoat or pick up some new shoes, please read this first.
My first pet peeve is something that should be fairly obvious to most men, but unfortunately is not. Should you receive a sport jacket or overcoat that has not yet passed through a tailor’s hands, please snip out the basting stitches which keeps the various vents and pockets sealed shut during shipping. Though the fact seems to escape some men, let me be clear: they are supposed to come out. Pockets are meant to be opened as are vents. Particularly annoying to me is when I see some guy out on the street in a dark overcoat with its rear vent stitched closed with a big white X. It makes me want to carry around scissors all winter long.
Another outerwear issue which I simply cannot fathom is wearing a short ski parka over a suit jacket. The effect of this totally inappropriate clothing choice creates a tutu-like effect with the skirt of your jacket; not to mention the damage and wrinkled inflicted on your good clothing. This look is simply juvenile, incongruous, and in a word, laughable. Your outer coat should always be longer than the suit jacket or sports coat. Please don’t do this.
Lastly, a big pet peeve of mine is fake dress shoes. You know the ones – trainers doctored up to look like oxfords. I hate to break it to you, but you’re not fooling anyone – really. It just looks wrong for so many reasons, not the least of which is that when those awful shoes are sighted, whatever else you have on is more or less ignored.
Men often complain about dress shoes being uncomfortable, which to me means that they are wearing the wrong shoes. Dress shoes should be comfortable all day long. Are they just like a pair of sneakers? Of course not, but you don’t wear sneakers with a suit – well, actually in some cases you can but that’s for another day. If you have persistent arch pain or other foot issues, see a doctor and consider investing in some bench made footwear or custom orthotics.
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Mastering the Rumpled Look
Cooler weather is always more kind to men when it comes to getting dressed in the morning. We can layer, pull out the cords, throw on a chunky jacket and top it off with a warm scarf. The sheer variety of cool weather clothing is something many a man looks to as the thermometer drops.
For those of us with the flexibility to move between business dress and corporate casual, what I call the “Rumpled Look” is a middle alternative to just dressed up and dressed down. Originally an offshoot of the American Preppy aesthetic, the rumpled look has come into its own.
The basic idea behind this style is the allusion to old money, classic taste, and timeless style. Newer or continental styles don’t lend themselves to celebrating beat up and handed down clothes quite like the preppy culture does. The unspoken message of the slouchy khakis, un-ironed oxford shirt and slightly beat up shoes is that you have old money, an Ivy League education, a summerhouse in the Hamptons, and you sail a lot. Or at least you dress like you do.
I have to say that this really is a fun look which is not hard to carry off well as long as you don’t try too hard. Like the current “critter” trend, with pants, ties, belts and coats are adorned with embroidered animals and icons of every sort – dogs to martini glasses – less is more. One creative article of clothing at a time is ironic, more is overkill.
For most men, wearing this look at the office can be a bit tough, but depending on your company’s culture, distressed chinos matched up with a wrinkled button down under a crewneck sweater should be just fine. For a younger look, don’t tuck in the shirt but rather let it hang out under the sweater. Wear a washed tweed jacket over the whole outfit. This kind of layering effect is another signature of the rumpled look. To meet up with friends for drinks, try pairing a permanently wrinkled Thomas Pink dress shirt with dressy jeans and a sport coat. The juxtaposition of classic and casual is a key balance to this look.
Like any other style you want to incorporate into your own, stop and look in the mirror before leaving the house. You want to be happy with the overall feel and proportion of your outfit. The goal should be to look like you’ve had everything for years and don’t think twice about getting dressed.
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Ralph Lauren as Historian
In case you have been living under a rock somewhere, it may come as a surprise that Ralph Lauren, the company, turned 40 this year. What’s really surprising is that at one point in time there was no Ralph Lauren; kind of hard to imagine really. Lauren created the concepts of lifestyle marketing, aspirational customers, and with the opening of the Polo Mansion, total immersion product presentation. No other designer has to his extent, actually become his brand. While many are closely identified with their labels, Ralph quite literally is Polo, Ralph Lauren, Purple Label, RRL, and Rugby to name just a few. That his company has so remade the retailing and luxury lifestyle landscape in only 40 years is the really amazing part. If you think about it, he didn’t really hit his retailing stride until the mid 1980s. That makes it even more impressive.
Lauren has been busy publicly celebrating his anniversary and I for one don’t blame him. Those of you who are regular readers of my blog OffTheCuffDC will recognize my particular affection for Mr. Lauren. For this I do not apologize. People are endlessly fascinated by him and his company. More than any other brand, Polo/Ralph Lauren invites you to live inside its world: wear its clothes, clean up with its soap, splash on its cologne, sleep on its sheets in its bed, decorate your house with its paints, and eat in its restaurant. Now, after decades of relative mystery, Ralph Lauren the man is opening up the doors a bit.
With his new enormous now coffee table book, “Ralph Lauren,” virtually every collection and associated marketing campaign is given the chance to shine alongside a retrospective of his own life. Additionally, the Discovery Channel recently ran a fascinating documentary on Ralph Lauren’s vintage automobile collection: “The Ralph Lauren Car Collection: Speed, Style & Beauty.”
Considered to be one of the finest of its kind in the world, this collection encompasses many marquee names - Porsche, Ferrari, Mercedes, Bugatti - but the quality and stylistic breadth of the cars is staggering. Restored to a level that in some cases exceeds their original showroom quality, his cars track the development of the automobile not only as transportation, but as art and social elegance.
The hour-long exploration of the collection examines how it came to be, the development of the obligatory companion book, and how his cars have influenced Ralph Lauren the designer. Lauren also graced the covers of recent Men’s Vogue, Fortune, and Town and Country magazines.
Another legendary collection of Lauren’s pulls at my soul: his assemblage of watches which range from vintage Rolexes to a one-of-a-kind collection within a collection of Panerai Italian military watches. Watches in particular are intensely personal items that convey a true sense of individual style. A collection like Lauren’s is in many ways a mirror of his personality and certainly seems to accurately reflect his obsession with quality, purpose, style, detail, and history.
This past March Ralph Lauren and the Richemont Group, owners of such luxury brands as Jaeger-LeCoultre, Mont Blanc, IWC, and Alfred Dunhill, signed a deal to create The Polo Ralph Lauren Watch and Jewelry Company. The 50/50 joint venture will design, manufacture, and distribute products through Polo boutiques and exclusive high-end jewelry stores. It seems that Mr. Lauren is ready to add his own creations to his personal museum.
By assembling these fascinating collections, Lauren is becoming a curator of historic touchstones that define luxury and elegance. While some may see this as a homage to conspicuous consumption or a celebration of indulgent decadence, I look at it very differently. Watches and cars, clothes and shoes, bags and furniture; these are the things that people use to define and identify themselves the world over. They are expressions of personality and elevate functional objects to the level of craftsmanship.
Ralph Lauren is consciously preserving the history of practical elegance. He also uses his collections for personal and professional inspiration; think of them as a database of style from which new Polo creations evolve.
Look around your own life; your home, your closet, your dresser, your briefcase. What daily objects can you say are unique and truly important to you? If for example you have a mug full of pens on your desk but only one or two vintage roller balls actually mean something to you, get rid of the others. Use the things that matter and don’t hold on to stuff just because you have it.
While most of us do not have his financial resources, take a page from Ralph’s playbook and don’t just accept what you can get; don’t keep what happens to be around just because it’s there. Rather, select the things in your life and regularly edit. Create your own personal collections and you will find more value, financial and personal, in fewer but cherished possessions.
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Dressing up Jeans
Jeans. For some people they symbolize lazy weekends; perhaps paired with your favorite old tee shirt and beat up trainers. Perfect for washing the car or walking the dog. For others they connote urban hip; the ultimate counter play to formal office wear. Ralph Lauren made news when he wore jeans with his dinner jacket to receive a major award. Far from being social faux pas though, it was instantly understood to be a very “Ralph Lauren” look and launched a thousand failed imitators. What he made look sharp and fashion most people simply butcher.
Jeans can be dressed up, but never make the mistake of thinking they can replace dress trousers, suit pants or, god forbid, tuxedo pants. People in the fashion business can get away with such things because they are in the fashion business and to their peers this is messing with the vernacular in a creative sort of way. Everyone else, myself included, should tread lightly when it comes to bringing jeans into the office. Still, it is possible to dress up jeans for work, a nice dinner, or cocktail party. Just focus on some key rules.
You should own at least one pair of dark blue jeans; they are timeless and the most versatile type you can own. Dark blue jeans can be dressed up with a collared shirt, sports coat and brogues, or dressed down with a tee shirt, cashmere crewneck sweater and moccasins.
Remember this: your jeans should fit you. I read a very funny article recently about “dad jeans,” which highlighted the sad fact that over the years most guys fail to buy new jeans and instead perpetrate a self-delusional myth that their favorites will always fit. They don’t; and while the jeans may stay in top form, you dear reader will probably not and it will show.
Although there are all sorts of fits and cuts, your best bet is still the basic strait leg version. It should sit at your natural hip and have a nice moderate break over your shoes. Alternately, you can wear them rolled up a bit for a preppy take or tailored to exactly hit the top of your shoe. Whatever your choice, they should look comfortable and trim but not tight; certainly not baggy and low-hanging. As with most things in life, simple is often better.
Dark jeans in particular lend themselves to more dressed-up outfits. They can carry off dressy casual better than their stonewashed or “vintage” brethren because of their inherent sophistication. In most outfits a good pair of dark blue jeans provides great texture and personality. Of course, if you want a laid back casual preppy look, most distressed and faded styles work fine as long as you stick with well-fitting strait leg models.
For autumn, try pairing your jeans with a high quality dress shirt and sport coat – tweed or corduroy look great. Throw a vest in between to add some warmth as well as style. Trim jeans can carry off dress shoes particularly well. The juxtaposition of elegant leather footwear and rugged denim is very attractive. As noted above, jeans and sweaters are always a great mix.
By approaching a good pair of jeans as a part of your wardrobe and not just something thrown in the corner, you will get more out of this versatile workhorse.
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My Style Influence
In a discussion not too long ago, someone asked me who has had the most significant style influence in my life. Though I assumed that an actor, designer or even a politician would be the winner, what almost immediately popped into my head was a little surprising. Since most people’s personality tends to be the sum of life events as well as genetics, I thought you might find a story that combines both a little interesting. If nothing else, I’d like to think of this as a brief testament to finding true class right at home.
Though not my initial thought, it quickly became obvious that the most powerful influence on my personal style has been my father. While I have had many influences over the years, from magazines and movies to working in a couple of Ralph Lauren stores; my core view of what defines “style” is firmly grounded in him.
As is often the case with children, I never really appreciated as a boy his wonderfully classic sense of taste and respect for quality. It only hit me after I had grown up and moved on with my life. Though he himself would eventually grow up to live a decidedly preppy handbook kind of life, he was by no means born to it. A keen application of hard work and long hours in the library eventually led to a New England prep school and then an Ivy League college. The result is a man who, though having very traditional taste and an appreciation for the classics, is without pretense. He has never forgotten his roots.
As to his personal style, my dad’s version of a sweatshirt and jeans are khakis and a corduroy sport coat. It is simply what he grew up with; as he once told me, “I’ve worn a jacket every day since grade school, I had to.” As a result, he has always managed to look completely comfortable in such attire without being the least bit stuffy or off-putting. This is a real accomplishment as, literally, he has never actually owned a pair of jeans. To the contrary, he has always been an approachable guy which is very important because he is also doctor.
One particular memory of my father will always stick with me because it showed how clothing can so define the inner qualities of a man. I was with a friend who worked at our local hospital and we stopped by the emergency room so he could drop something off. While I stood in a corner, watching the commotion and trying to stay out of the way, I saw my dad come around the corner. As it so happened, he looked great; seersucker suit and white bucks – downright natty, actually. He didn’t see me.
What happened next will forever stay in my heart and mind. He walked over to an elderly man lying on a gurney parked along the wall. Very gently, he leaned over and began to talk with the gentleman. Their heads close together, I could see the body of my father’s patient relax. At that moment, what he had on was irrelevant; he was there to comfort and help his patient. I then recalled something he had once said about always dressing well to make his rounds at the hospital: it wasn’t for his benefit; rather it was a sign of respect to his patients. He paid attention to how he dressed because his patients deserved at least that.
In that moment, the style on the outside very much matched the man on the inside. It’s easy to dress well, but that’s not the same thing as having class. More than any magazine or movie star, that image will always be my definition of true style.
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• Ruffs, Cuffs and Farthingales (by Winston Chesterfield)
• BespokeMe (by Andrew Williams)
• Man about (London) Town (by Matt Clarke)
• Parisian Gentleman (by Hugo Jacomet)
• Smarter Style (by Michael Snytkin)
- gary: great post. put it on my blog if you...
- Harry: On a matter of personal taste, I...
- Peter: This article echoes my own interest...
- Andrew: I hope we will get to see pictures...
- Winston Chesterfield: My most recent choice...





