#Boyswear: How to Get Boys to Dress and Act like Gentlemen

We all know how the #menswear movement has taken the internet (and the world) by storm. More men than ever in recent years are upholding and promoting a classic style. But what about the next generation of little men–our young sons, grandsons, and nephews? How do we inspire them to have an interest in dressing well? What clothing should they wear and how do we outfit them?

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.

Until last century, boys wore dress-like garments in their early years. Pink was also a color associated for a long time with male children.

Until last century, boys wore dress-like garments in their early years. Pink was also a color associated for a long time with male children.

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.

Three generations of British princes in traditional shorts

Three generations of British princes in traditional shorts


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.

Expand a boys' wardrobe beyond the typical t-shirts and jeans.

Expand a boys’ wardrobe beyond the typical t-shirts and jeans.

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.

3 season suit by Black Lapel

Your style will have an effect on the children around you

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.

Frank Galluci acting as a style role model at Pitti Uomo.

Frank Galluci acting as a style role model at Pitti Uomo.

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.

School uniforms that are too large.

School uniforms that are too large.

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.

Emmett wearing a bright blue jacket and tie with a geometric print that is appropriate to his age.

Emmett wearing a bright blue jacket and tie with a geometric print that is appropriate to his age.

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.

Big and mini versions of @burezaonline attending Pitti Uomo.

Big and mini versions of @burezaonline attending Pitti Uomo.

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.

Let kids experiment with personal style without harsh judgment even if they want to wear sneakers with a suit.

Let kids experiment with personal style without harsh judgment even if they want to wear sneakers with a suit.

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)

First, the fact that kids grow, and often rapidly, makes dressing them well potentially expensive, unless you’re Kanye West, who notoriously puts his kids in thousands of dollars worth of Balenciaga. The solution, as with anyone who wants to pursue style on a budget, is thrifting. For a tip, you may want to check out thrift stores in upscale neighborhoods or those that specialize in finer wares. As mentioned earlier, you can also settle on cheaper department store brands provided they fit well and are examples of good taste; they will damage or outgrow stuff anyway.

2. Kids Get Messy Quickly

Boys get dirty and aren’t particularly careful about maintaining their clothes in an orderly way. As adults, we may carefully avoid sitting on a dirty bench when wearing light grey wool trousers and tuck in our shirts if they become untucked, but we can’t always expect a boy to show the same self-awareness. Teach him how to take care of his clothes, but get washable or stain resistant garments and favor dark over light colors nonetheless. Again, children shouldn’t be confined by what they wear, so it’s not worth getting fastidious about keeping them clean. Besides, when boys are indifferent to maintaining perfection, you can chalk this up to a kind of natural sprezzatura. If they forget to button the collar on an OCBD or purposely open up their sleeve buttons, they are unselfconsciously achieving something a lot of the #menswear crowd are aiming for!

3. Society Trends Are Against You

Living in a casual society certainly doesn’t help with the resistance boys may feel about dressing well. Nearly everyone around them is dressed with little attention to polished presentation. Moreover, many adults and the popular media enforce the idea that wearing ties and suits is uncomfortable, or merely a way corporations create conformity and turn men into office drones. The lapse of etiquette in contemporary society also means you’re paddling upstream when trying to teach gentlemanly behavior to a young man. These are major challenges you have to overcome. However, by simply modeling your own comportment and showing that there is another side of being well dressed, you can counter the current state of affairs.

4. Kids Are Trendy

Another challenge to properly outfitting boys is that kids tend to be trend chasers; they are conditioned at an early age by advertising to prefer the latest fashion over clothes with a timeless appeal, an attitude that is only fed by their peers and what celebrity kids are wearing on Instagram. The solution, once more, is to furnish the fundamentals on style that transcends fads and take what you can get.

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.

Preppy style shown by Dartmouth freshmen in 1964,

Preppy style as worn by Dartmouth freshmen in 1964

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.

An example of Hackett's boyswear.

An example of Hackett’s boyswear.


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.

#Boyswear: How to Get Boys to Dress and Act like Gentlemen
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#Boyswear: How to Get Boys to Dress and Act like Gentlemen
A primer on how to get the next generation of little men started on dressing well.
Gentleman's Gazette LLC
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16 replies
  1. Eric Seabury says:

    I am glad you posted this.

    I have a 12 year old son who loves James Bond and Kingsmen movies, World War II history and the U.S. military.

    I am also a fan of these things and I try often to dress classically. It’s rubbed off on my son and now he wants to own a suit, he combs his hair until it looks meticulous.

    After watching “The Philadelphia Story” in the cinema recently, he had asked me how did men dress while going to the movies in the 1940s. Now, the next time we see a classic movie, he wants to wear a suit (And has asked me to show him how to tie a necktie).

    Fortunately for me, my son wants to learn how to be a classic gentleman. In fact, we are going to go on this journey together. Learning how to dress, how to conduct ourselves at a restaurant, how we dress and act while travelling and taking up hobbies, such as golf, wall climbing, skiing and learning another language (He wants to learn German).

    He likes the idea that we will try to “Live like Bond”.

    Your article arrived at the perfect time. We will be certain to watch all your videos and read your links.

    Thank You!

  2. David says:

    Good article….Mr. Sven…however…Fathers should teach and command their sons on how to be gentlemen…not the other way around.

  3. Michael Patterson says:

    I applaud this article! As a professional in the Boy Scouts program, preparing youth for life is my passion. It’s especially important for today’s boys, many of whom may grow up without father figures. My father grew up without his father involved in his life and so the teaching of style never happened for him so it limited him in what he could teach me. GG has been a life saver for me and I intend to pass on this knowledge to my kids.

  4. James de Saxton says:

    A very good read, Dr. Lee. I have a teen daughter (many of the same principals apply) who demonstrates sophistication and taste well beyond her years, but is somewhat reticent to show it around her peers, whose staple is denim and glittery collarless shirts of varying type for the greater part. They are quick into my wife’s evening gowns when she has guests for the night, though.
    I suppose an article on daughters might not be too far beyond the scope of GG, as more than a few of us have them.

    • Michael Patterson says:

      There are some really good video series out there from glamour and cosmopolitan magazines that show classic attire throughout the decades. Very worth a watch for any young girl that is looking for a way to class it up.

    • Dr. Christopher Lee says:

      Thanks, James. Indeed, the principals go beyond gender. As is often the case, my wife was better dressed than I, and now we do it together. Many of the fashions for young women and men these days lack sophistication. Especially for young people, dressing well would give them greater presence and authority to counteract the biased assumptions others may have about youth.

  5. Omar says:

    Thank you for writing this feature. The importance of maintaining good conduct, taste and etiquette is all the more challenging when standards are declining around you.

    • Dr. Christopher Lee says:

      Can you elaborate, John? Do you mean children should always receive new clothes even if they outgrow them rapidly? Certainly adult men use thrift shops regularly to build wardrobes; all the more reason parents should draw on the same resource. If you are able to afford new clothes for yourself and the boys in your family, more power to you!

  6. anonymousthankyou says:

    I’m 16 years old and from South Florida. I began liking James Bond films when I was about 8 and grew a taste for dressing nicely. For years I’d wear suits on planes and for some events. Around the time I went into middle school I lost that confidence and went through my glued-to-phone lazy millennial stage. Up until the past couple of months I’ve begun admiring old movies and the way things used to be, what it’s like to dress and be a real man. I dress up for dinner and I prefer collared shirts over t-shirts, chinos and khakis over jeans, and oxfords/loafers/boots over sneakers. I happen to live in an extremely casual northern Ohio city and to see anyone try dressing anywhere near nice is next to impossible unless it depends on your job. My father having been a man’s man and a good dresser back in the day has been able to help me transition into the man I am now, mainly with just simple questions I’ve asked. The difference between me and 8 months ago is I now shave every other day, I wear a pinky ring, I dress respectively, I care how I look, I do my hair in the morning, I enjoy the finer things in life, and I carry a level of class in personality and dress. Ever since I’ve found Gentlemen’s Gazette I’ve been addicted. To know that not everyone is conformed to this ultra-casual, ultra-lazy society is great.


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