The J. Crew store in an outdoor suburban mall was packed with people snapping up discounted winter items and eyeing the new spring collection for men. As a long-time industry person, I could not help but notice something wonderful about this collection: it’s more-or-less the same as it was forty years ago. Not much has changed in this paragon of preppy casual.
And good for them. Shopping here provides a reliable, traditional, and time tested wardrobe for casual wear, pre-selected to provide men with a look that suggests rootedness. It’s wonderful but what happens when men want to dress up more? Here is where matters start to go very wrong.
A self-deprecating story to begin why this issue is important for me. It was in my late high-school years that the power of clothing became obvious to me. It’s a sorting system, a class indicator, a signaling mechanism to speak without talking. It always has been.
I needed some serious dress clothing. So I started looking at magazines on menswear. I saw a dignified man wearing a double-breasted white blazer with gold buttons plus black jeans. The look was amazing. I thought I needed to look like that.
I marched over to the Ralph Lauren Polo shop. The place was a bit ramshackle, consistent with the preppy ethos of the time. Knowing exactly what I wanted, I interrupted the clerk who was playing a golf game of putt-putt on the showroom floor. I told him of the blazer I wanted to buy.
The clerk scoffed. He looked me up and down. He said with an arrogance that gave offense: “You don’t need that. You don’t even have the basics, like a plain navy blue blazer.”
I sulked away, thumbed a few blazers and made my way out the door. The trouble is that he was correct, and I knew it. An experience like that burns into one’s memory, such that I can perfectly recall the scene now all these years later. Sure, the guy was a jerk but the truth also hurts.
The exchange did something else for me. It made me allergic to passing fashion, and caused me to realize that the basics are so essential that one hardly needs to move beyond them except in perhaps small ways. He was right about another thing. Most men today do not have the basics. They dress every day in something or other but have no understanding of what they are doing.
On the blue blazer, this is wholly correct. Every man needs a navy blue wool blazer, ideally with brass buttons. It’s remarkable what this one piece of clothing can achieve. You are wearing jeans, sneakers, and a tee. Throw it on and look in the mirror. You suddenly have the illusion of looking dressed up, even presentable. Show up at a party that way and you will be fine.
With one of these in the closet, you have done probably a third of the work you need done to be properly dressed.
Get some gray pants, a white shirt with a collar, a tie, and some decent shoes, and you have the makings of a genuinely good look. You can substitute khakis, olive trousers, different shirts and ties, and you have the makings of a solid casual wardrobe. Whenever an invitation says business casual, this is what you wear.
You might say, but I don’t want to look like everyone else. Fine. But look around: other men apparently don’t know this secret. That gives you a huge advantage in terms of looking sharp, aware, mature, and decent. Once you get the hang of grabbing it from your closet, you will find ever more reasons to do so. Even just going to the grocery store, the clerks will treat you better and so will other customers.
What else is part of a basic men’s wardrobe? You need a couple of white and blue shirts with collars, a selection of ties that are not weird, khaki and gray pants, and good dress shoes from a good manufacturer.
What about other blazers? In winter, you need a tweed jacket of some sort. These are incredibly versatile too. You can wear them with jeans or wool trousers, sweaters and shirts, or a turtleneck. For anyone in a cold climate, a tweed is essential. In warmer seasons, a cotton blazer works too—blue or khaki.
Make sure that it has a standard look and it’s not a fashion piece. The reason speaks to a much bigger issue. Fashion comes and goes. Chasing it is like trying to vaccinate against a mutating virus. It’s just not possible. Sure, vendors want you to believe otherwise but that’s their self-interest speaking, not yours.
There is a more practical reason. Let’s say you own a tweed with bright green and purple checks and a flap breast pocket. Or it’s hunter green with yellow checks—something that stands out and looks great. You will get all sorts of compliments.
The trouble comes the second time you wear it. Everyone in your social circle will remember it. The second and third time is less impressive. The fourth time broadcasts the possibility that you don’t have anything else.
Here is the problem of fashion. It fades. Permanent wardrobes do not have that effect. You can wear a navy blazer every day and no one will think ill. It merely suggests that you know what you are doing, have a look, and dress with confidence. This is how it should always be.
As for suits, you certainly need one or several. Pinstripes are great and so are subtle plaids, and solids too. The black suit makes a fashionable return every decade or so but, actually, they are only suitable for funerals. Otherwise stick to the core color template: blues and greys. Browns don’t really work as suits for some reason.
Now let’s get to some details that really matter. Whenever men come into the Oval Office and sit down, if they are wearing fancy socks with pictures or designs, Trump will comment: “Nice socks.”
That’s not what he means of course. He is subtly pointing out that a man’s socks should not be an eye-catching part of a man’s wardrobe. They cover the space between the bottom of the pant leg and the shoe and should integrate the two, not stand out. This is why they should be solid blue, gray, or black. Ideally they should be over-the-calf so you don’t have to tug on them and so that they don’t show flesh.
And I’m sorry, but there is just no way to make wearing loafers without socks look anything but unsanitary. I will never understand how that trend was started in the first place.
On fit, the shirt sleeve should fall below the jacket by a half inch (more or less), trousers should not drape around the shoe but barely break, and a gentleman’s trousers should hit the waist much higher than jeans. For some people, this takes some getting used to.
Also, there is a reason for the existence of undershirts. They keep the dress shirt clean and make it look presentable instead of adhering to your skin and revealing vague flesh tones. Every man should have a half dozen or so and putting them on should be as routine as wearing underwear.
As for outerwear, puffy coats and jackets are just not suitable for most occasions unless you are hanging out at the ski lodge. In the city or about town in the winter requires a serious overcoat, single- or double-breasted, made of wool or cashmere.
Finally, it really matters that you have an iron and ironing board and learn how to use them.
As for expense, the only item above that should really set you back are the shoes. Buy great ones, ideally American made, and you will have them for life.
Otherwise, you can get most of above on eBay. Fear not “used” clothing, for this is your source of fantastic things at a fraction of the retail price.
In my experience, men are deeply insecure about clothing beyond weekend wear at J. Crew. This need not be. It’s infinitely easier for men than women to dress themselves properly, provided they have the basics.
