A Brief History of Clothing for Boys
In Europe from the beginning of the Early Modern period (the 1500s) even up to the early twentieth century, young boys wore the equivalent of a dress up until the age of seven or so, when they would be initiated into wearing pants. This was referred to as a breeching, which was marked by a ceremony as an important moment in a boy’s development. Wearing breeches often coincided with the “age of reason,” when children were thought to be able to understand the consequences of their actions though it could be done as early as age four. Putting boys in dress-like clothes before this, which often makes it difficult to distinguish male and female children in paintings, was a practical consideration that made toilet training easier and facilitated clothing alterations as the child grew. From an ideological perspective, unisex clothes showed that children were innocent and pre-sexual.
In English-speaking countries, during the nineteenth and twentieth centuries, boys usually wore short pants in childhood and would only graduate to trousers when they hit puberty. Even today the association remains; adult men wearing shorts outside a beach setting are often labeled as juvenile by those who uphold the traditional rules of dress. Long pants marked a true transition to manhood. When boys were breeched, they were also expected to conform to the norms of masculine dress of the time period when they were in public–for example, they had to keep their jackets on–and they had little choice in what they could wear. However, being children, they generally had more freedom than men in how closely they were required to follow the rules of dress. Nowadays, the freedom boys have to wear what they want has definitely increased, and, since the rise of casual wear, many adults would consider putting a boy in the equivalent of a suit on a regular basis a form of cruelty and confinement.
Getting Started: Expand their Wardrobe
Given that boys were not held to the same standards as men even during a time of strict dress codes, we should also be flexible in dressing them today. Though we may be obsessed with traditional style and may refuse to go without a sport coat even in the dog days of summer, we can’t insist that our sons and grandsons do the same. Essentially, you want to sow the seeds of good taste where clothing is concerned and try to get your kids to dress well at least some of the time. Take it slow and start with small changes if you need to. In traditional households, mothers are the ones who choose and buy clothing for the children, so this is your chance to provide input as a gentleman of style. You might start by building a wardrobe that includes shirts with buttons and proper collars, flat caps, cardigans, and leather shoes, for example, instead of (or in addition to) the usual jeans, sneakers, baseball caps and hoodies with dinosaurs on them. Smart casual is a safe target as well, and tracking the styles of the photogenic Prince George of Cambridge wears is one way to get ideas.
9 Ways to Get Boys to Like Dressing Up
Even if you diversify a boy’s wardrobe, it’s useless without building a foundation of knowledge and interest. For many boys, their first exposure to tailored clothes–a blazer and dress pants or a suit–is as a school uniform. Otherwise, it’s at a special occasion like a wedding or funeral or at a weekly religious service. In one case, they’re forced to dress up and wear essentially the same thing each time, and in the other, they get the sense that dressing up only happens occasionally. So, the first hurdle is convincing boys to enjoy being more dressed up outside of these situations. This is not unlike convincing grown men that tailoring isn’t only for the office, but it’s better to start early! Here are nine techniques and tips to create a lifelong interest in being a gentleman.
1. Be a Style Role Model Yourself
First, simply by enjoying and wearing classic menswear yourself, you can serve as a role model for the young men in your life, at least until they become rebellious teenagers. Boys want to be like their dads or adult men they know. If dad is well dressed, a boy will be more inclined to emulate than if dad also hates to wear a suit to work. I remember vividly a math teacher I had in junior high or intermediate school who wore an array of three-piece suits when he taught a class. He was of Italian descent if that had anything to do with it. I also recall how meticulously he styled his hair and beard. I may not remember how to do trigonometry anymore, but I remember him decades later as a style role model.
2. Get them Clothes that Fit Well
When kids talk about their school uniforms they usually express how they dislike them, but the reasons are that they’re uncomfortable and ill-fitting. Getting clothes that fit well, whether a uniform or outside of school, is paramount to remove the dislike of dressing up. The advice is the same for men buying a suit–if it fits well, it creates a sense of enjoyment and confidence. If boys are made to wear a jacket that is too big or pants that puddle around their shoes from being too long, they’ll hate being dressed up. The fit doesn’t have to be as perfect as it does for the connoisseur of men’s style, just good, and having some tailoring done is a modest financial investment in shaping a boy’s positive attitude to structured clothing.
3. Dress Boys to Suit Their Age
Though they may have only been in the world for a few years, the maxim of always dressing your age applies to boys too. You don’t want to put a boy in chalk stripes or somber colors, for example. Instead. go with brighter hues of blue and choose accessories with fun patterns like geometrically printed ties; these still have a sense of childhood about them. Kids will intuitively know when what they’re wearing is or isn’t appropriate to their youth.
4. Dress Them Like You
Dads who are outgoing can also opt to do a “mini-me” sort of thing, dressing their sons in a similar or matching outfit to theirs. If you wear a tobacco linen suit, a tie, and a Panama hat, your son could wear a vest and pants in a similar color or fabric. This gets a lot of attention and will definitely be seen as cute, so it works well at special events (including Pitti Uomo!) but not every day. Many kids like attention as much as your typical Pitti Peacock, so they may be game to getting a taste of tailoring. Boys are proud and will smile widely if they are complimented their clothes. If your pockets are lined with gold, you can certainly go full matching bespoke for both of you, but you can easily coordinate on a budget as well.
5. Get Them Interesting Books and Resources on Classic Men’s Style
Beyond just being you, introduce the boys in your family to some books on menswear. Many of us can remember looking through printed works when we were growing up, like the DK Eyewitness Books or the World Book encyclopedia, that combined information with pictures. Many coffee table books of interest to gentlemen or books specifically on men’s style do this. Let your young man look at a copy of Bruce Boyer or peruse The Italian Gentleman. If not books, direct a boy you know to the abundant videos and articles on The Gentleman’s Gazette. If anything, by osmosis they’ll absorb what good style looks like, but it is equally likely you can instill some memories and develop interest.
6. Take Small Steps and Compromise
You can educate a young man about classic style and basics like how to pair blue and gray. Give them sartorial fundamentals, including color combinations, but always let them take things at their own pace. Maybe they’ll show you one morning that they can pick out clothes to suit the occasion. Maybe they’ll want to wear a tie to the movies. Count these as little victories based on the foundation you’ve laid.
Similarly, you likely will want to compromise where kids are concerned even if you wouldn’t for yourself. Even if you would never wear wrinkle-free shirts because of their sheen, you might still buy them for a boy since they look better on an active child than a shirt that needs to be pressed carefully and worn with care. You know not to buy suits made of synthetic materials, but for the sake of budget, you don’t need to lose sleep buying a well-fitting polyester suit for a child who will outgrow it within a year.
7. Participate in Gentlemanly Activities Together
Establish the interest early not only with books but with hands-on activities. These also create bonding opportunities, activities you can do together, which are ever more important in an era where young people sit alone in front of screens during their free time. Knowledge transmission is also important. Throughout history, men have taught the next generation of boys how to be gentlemen, including the art of dressing and grooming. David Coggins’ book Men and Style contains several sections of interviews and testimonials from well-dressed men of today talking about their early years and the memories they had of the way their fathers and grandfathers dressed. Nowadays we read comments online from so many young adults in their twenties who don’t know the basics because they were never taught. Sites and online resources like The Gentleman’s Gazette have acted in loco patris to help transmit this knowledge, but if you can teach the next generation directly, firsthand, so much the better. When I was growing up, my grandfather had an awesome shoeshine kit with Kiwi wax polishes, horsehair brushes, buffing clothes and more. I would watch how he polished his shoes and eventually did it for him. To this day, I enjoy the ritual of shoe care, and I can do it well.
Starting young is the key. The accouterments of menswear can be fascinating to a boy who wants to learn, who is eager to be like a grown-up man. Teaching the art of shaving is usually spoken about as the defining father-son moment, but skills such as tying a necktie with a proper dimple, tying a bow tie, or tying their shoes the right way are all excellent opportunities.
8. Let Them Choose
As mentioned at the start of the article, kids today have unprecedented choice compared to their forebears. Sometimes they will choose wrongly, like wanting to wear sneakers and a suit, a skinny tie, or a Merovingian knot that makes you want to cringe. Part of their self-development and individualization involves the process of personal discovery. You can make suggestions and direct them, but let them experiment. Nothing kills enthusiasm and ruins learning more than disapproval. As adults, we’re still learning every day about how to improve our style, and our mistakes find their way onto eBay; kids should have even more margin for error. Even if you need to settle for the long game, and it takes them until they’re 30, they’ll eventually realize the importance of the style lessons you taught them.
9. Teach the True Meaning of Being a Gentleman Today
As part of inspiring youth, I would urge all men to act as teachers and role models for the boys in their lives, not just in terms of style but in all aspects of what makes a gentleman. This means things like etiquette and table manners, how to accept a compliment, and respect for others, particularly the opposite sex, which the #MeToo movement has shown to be sadly lacking in many men. These lessons can bear fruit immediately when other boys are running amok and screaming at a wedding or farting in a restaurant while your young man is well behaved. They also obviously have a long-term impact on their adult lives.
6 Obstacles to Dressing Boys Well
We’ve already mentioned the negative association boys may have when wearing tailored clothing, especially as a school uniform. Beyond this, there are a number of other challenges that you may face as you try to get a young man to dress well.
1. Outgrowing Clothes (and Your Budget)
2. Kids Get Messy Quickly
3. Society Trends Are Against You
4. Kids Are Trendy
5. Bullies Will Make Fun of Them
When I went to (public) high school in Brooklyn, there was a student from Jamaica who transferred in mid-year. He wore a navy blazer and tie to school each day by choice and always carried a tightly wrapped full-length umbrella; he looked like he stepped out of Kingsman. For this, he was the object of mockery and abuse by other boys, though he was popular with the girls, and I remember him because of his style. The fact is, if a young man dresses in any way that stands out or is different from the norm, he can invite negative attention and bullying; this is true whether he dresses up, down, Emo or Goth, not just in a way that evokes classic men’s style.
Adult men who dress well in workplaces where everyone else is casual are still ridiculed by co-workers. One solution is to limit being well dressed to “smart casual”: a nice buttoned shirt and trousers, for example. This can be a way of teaching him about dressing to fit the environment. The other option, depending on the personality of the child and how harsh the school environment is, would be for him to dress up anyway as a way to assert his individuality and be a trendsetter. Some of today’s best-dressed men, including Bruce Boyer, Sid Mashburn, and Jeremy Hackett, started by marching to the beat of their own drum when they were children or teenagers, as noted in David Coggins’ Men and Style. Maybe the next trend will be Kingsman style, started by your teenager.
6. Teens Will Rebel
Although you may have a younger boy who is receptive to your instruction on things of a gentlemanly nature, it’s still quite likely he will rebel against your style advice during the teen years. A trick here is to play the sprezzatura or Ivy style cards. Many of the fashion brands teens used to like–Ralph Lauren, Tommy Hilfiger, Abercrombie & Fitch–were influenced by Ivy, trad and preppy style, and even though they are less popular with teens nowadays, the style continues to hold some fascination. The originally rebellious nature of these styles, and the fact that they were started by young people just a few years older than them are appealing. The sprezzatura look is also associated with a cool nonchalance that teenage boys try to cultivate anyway, so they will buy into it.
Places to Find Classic Clothes for Boys
Beyond thrift, other secondhand marketplaces like eBay and Craigslist, and most department stores, there are a number of specialty menswear stores from which you can acquire more expensive items for boys. This might be an occasional indulgence or something for a special event. In the US, Brooks Brothers have one of the broadest selections of items for kids. In the UK, Hackett sells a wide variety of clothing for boys ages two to eighteen. A few years ago, Drake’s of London sold boys’ ties; they no longer do, but, you never know, they may again.
If we want to make the #menswear movement count, to bring back classic style or, at the very least, keep it alive and vibrant, we have to teach boys to be interested in it, to embrace the ethos. We cannot underestimate the value we have as male role models, not only of style but of gentlemanly behavior. What are your men’s style memories growing up, or how do you teach the boys in your life about menswear? Have you encountered examples of #boyswear? Share your experiences in the comments section below.