How To Convince Your Little Boy To Dress Up? 6 Tips To Get You Started!

How To Convince Your Little Boy To Dress Up? 6 Tips To Get You Started!

Today is about your little boy.

What should it be? Gentleman style or comfy?

What should a boy wear to look like a proper gentleman?

How to get boys to dress and act like a gentleman?

Or let me try a different approach.

What boys like to wear?

Because this is what matters at the end of the day, to have happy kids which come with a great prize (can you guess?).

Indeed. A happy and peaceful motherhood life.

If you have ever encountered some real struggles in convincing your gentleman boy to put on a comfy pair of sweatpants or vice-versa (because let’s face it, the idea of wearing a tailored tuxedo is not so appealing to a 10 years old bad-boy), then you’ve landed in the perfect spot.

I’m here to help you in developing your boy’s dressing skills and how to encourage him to find out his style. To figure out on his own whether he would like to be a gentleman or a sporty type of guy.

Ready? Let’s go!

Boyswear: Short History


Photo by Suzy Hazelwood from Pexels

The 1500s, Europe. That’s much or less the moment when we could talk about fashion in what concerns boys.

More precisely – they were dressed up in what we identify today as being a dress (preferably pink, because, guess what; until last century, pink was the no.1 choice for male-children outfits) up until they hit the age of seven which was the moment when they could have finally be introduced to the mighty pants.

Long story short, keep that in mind as breeching.

This breeching was celebrated with a ceremony and was seen as a major step in the boys’ development process.

And why dresses? Because it stood as an innocence symbol and created the connection for today’s unisex clothing items. (I feel so enlightened right now)

Back then, in the English-speaking countries, when we refer to young boys, we can imagine them wearing only short pants because they were allowed to upgrade to long pants when they hit puberty.

A fact which leads to a simple formula: long pants -> manhood.

Now let’s have a break and think about the restrictions that little boys had in terms of fashion choices in the 19th century and the ones that they have today?

Can you relate?

I guess it’s pretty obvious that nowadays boys’ freedom in what they can choose to wear is way larger, and sometimes leaves us with huge question marks, but the battle is not lost yet, so let’s see what can we all super-mamas do to recover our gentlemen.

Dressing Up Boys Can Be Equally Fun As Dressing Up Girls


Yes, dressing up boys can be as fun as dressing up girls, the only thing you need is imagination (which I strongly believe you have) and the will to do it.

That’s it.

Forget about the stereotypes. If you want your baby boy to be a little prince like in the 19th century (well, not the pink dress though), then go for it!

Let your imagination flow and implement the good taste in fashion from an early age.

You’ll thank me later. I’ll be here waiting 🙂

Ok, I hear you. I know that dressing up a girl is…let’s say, easier. You can simply put a dress on her and she’s perfect to go, but with boys, things get a bit complicated, yet not impossible.

So what should you do? Do you agree with me that our kids simply copy our behavior? Which includes also the way we tend to dress up.

And this leads me to the next point: that we can’t dress like we are going to attend a marathon, or wearing all the time jeans, a sporty coat and some old sneakers (like we’re following a dress code or something) and after that to expect our boys to be into elegant clothes.

The answer to the question above is to try to add the sense for good taste in clothing items from an early age and to encourage them to at least try from time to time to dress like a gentleman.

How Can Your Boy Become More Stylish?

Take it slow, one step at a time.

You, mama, have the power to make the change (and dads too, they play a major role in a boy’s way of dressing up) by simply adding one item of clothing at a time.

Start with a shirt with buttons and stiff collars, some cardigans, a flat cap, a suit vest and camel pants, some nice-looking leather shoes, and try to mix them afterward (like I did in the collage below).


I don’t say to give up on comfy baggy jeans and sneakers or that loose hoodie that he enjoys so much wearing, I just recommend, if you want and wish, to present options.

Who knows, maybe something nice can come out of this.

Simple Guide To Increase Boys Appetite In Dressing Up



You did the first step which is to enrich your sons’ wardrobe.

But this is not enough. It leads to the importance of building knowledge and interest for this topic.

Like Lego, piece by piece.

Let’s see. When does your boy meet the idea of wearing a fully tailored outfit?

Exactly. At school.

That dull and boring school uniform.

Or at a wedding, or…I don’t even know where else, probably at his baptism party, but after that, that’s kind of it, and this sad thing implements in their little heads that dressing up is only for the special occasions (if there are any).

So hold on mama, ’cause what you should try right now is to convince your little hero to dress up like a gentleman even if there is no special moment to do it.

Make him see it like something fun and natural to do. And here is how to do it.

6 ways to get it started!

1.You, as parents, be a model for him.


Yes, convince your husband to get you out at dinner, put yourself in the most beautiful dress you have, and help your husband adjust his tie (mmm, it’s getting hot in here), but do this in front of your boy.

Tell your husband to encourage your son to help him fasten his vest buttons or to put the handkerchief in his coat pocket.

These are little things that can also help the father and son bonding and is precious information that I can bet your boy will not forget any time soon.

Your husband is your son’s hero, so let’s play by these rules.

2.If it fits, it sits.



I think this should have been rule no.1.

Buy him clothes that fit him perfectly, or you can opt for tailored clothing, it’s up to you. If you do this, whether we’re talking about a school uniform or some spear time outfits, it is more likely to get away the idea of disliking the dressing-up thing.

Keep in mind: good taste is something that can be build and molded.

3. Dress your boy to reflect his age.


Yep, you heard me well. When I think of a boy gentleman outfit, I don’t imagine a 10 years old boy dressed up like my grandpa.

I’m thinking more about choosing light colors, like blue or cream, and don’t be afraid to accessorize with items that have playful patterns (like a tie with geometrical prints, for example).

It will emphasize the idea of childhood, so be aware, you can do this!

4. Father and son compilation.


Hehe, did you think that only moms and daughters have this privilege?

Well, that’s a big-fat-no-no.

Our boys deserve it too! So yes, dress you boy like his dad.

Remember the son and hero, right? So if your husband is wearing a camel linen suit and a flat cap, dress up your little champ with white a shirt and add a camel vest too.

He will definitely be the star of the show and win some hearts out there. This can also lift his self-esteem and encourage him to try this more often.

5. Teach and step back.


Teach your champ more about the classic style.

The basics.

For example how to pair correctly the colors (blue and gray for example) or textures, but keep in mind to let him follow his own pace.

Who knows, maybe one day your little boy will want to take you out at dinner like his father did and for this special occasion he wants to wear a tie.

How would that feel? Amazing! I Know!

6. Let them choose. No matter what.

Take a deep breath.

I’ll take it with you because I know it’s hard, but we have to keep ourselves strong for the storm ahead. Children know to handle things, even if you think they don’t, they want to explore, and it’s perfectly fine.

And this whole exploring thing is an important part of the self-development process and sense of style development.

Let them try and experiment, don’t touch, just say your opinion. It will be listened to, trust me.

You’ll see that sooner or later, your child will remember your gold lessons and when he will be a handsome young man, you’ll smile and know that what you see is what you’ve seeded.

Bonus Info For My Mamas: Things That Can Stop Boys From Being Stylish And How To Stop It

There has to be something wrong, isn’t it?

Well, if motherhood would have been easy, then you would have been able to see flowers and peace in the world, but this is the real world, and in the real world…motherhood happens.

So which are the things that can stop your champ from being a stylish gentleman boy?

1. Man! They grow fast!

Yep, they grow fast and unless you’re way too wealthy (can you tell me the secret, please), I find it quite challenging to keep your boy dressed up like Chuck Bass.

Every. Single. Day

The solution: try sustainable clothes.

Don’t feel too picky to accept clothes from older siblings or relatives, or even second-hands.

Man! They can have pure gold buried in there.

2. Oh! Look at me, I’m so well dressed! Let’s have a football game after school!

And here the beautiful dream ends. Should I say more on this? Can someone tell if there is actually something to do about it?

3. Bullying.

And that’s a topic that can be debated a long way from now.

I know it’s harsh, and it is a thing that kids have done and will do in the future too.

What can we do instead? Encourage our kids to be firm and support their choices no matter what.

4. Today’s fashion.

That’s it. I said it.

I said so many times that I’ve been born in the wrong era.

And I also agree that fashion nowadays is quite…odd. Especially when talking about kids.

So if we are to follow the steps that I listed in how to develop your child’s sense of style and take them shopping, well, the only thing they’ll see is mostly baggy jeans and hoodies, and…that’s it.

But if you keep your pace and implement the right information about how a proper gentleman should look like, there is nothing that can get over these fundamentals.

Your boy is smart, so he’ll know how to deal with fashion nowadays.



The only way in which we can revive the classic style or keep it alive and transform our little boys into real men is to make them interested in it.

My advice for you today is to keep pushing this information towards your husbands and encourage them to share their knowledge with their sons, it can change an entire generation.

Because we are talking about memories. And memories never fade.

What are your thoughts regarding this topic? What do you preach: comfort or elegance?

Thank you for reading me again, and good luck in raising gentlemen.

See ya, love ya,

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