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Fun Fashion For Little Boys

authentically amber how to dress little boys fashion and capsule wardrobe

When I first found out I was having a boy, I can’t deny I was a bit disappointed that I wouldn’t be able to take advantage of all of the fun baby girl fashion out there. Any “Boy Moms” know that in general, boy fashion can be lackluster. When you walk into any major store with baby clothing, you see rows and rows of girl fashion, all the pink, bows, dresses, bedazzled shoes, accessories galore, etc. Then you get to the boys’ section. It’s usually one or two racks of a few bland items, or even worse, the bane of my existence (cheesy licensed t-shirts and onesies), and those are about it. When I was pregnant with my first, I went into my favorite baby store to register, and as we walked past the girls section to the tiny and bland boy section, I got sad. I can’t fully remember, but I may have even cried.

After my sweet baby boy was born, I recall visiting a ritzy kids boutique, looking for a photoshoot outfit. The whole store (not exaggerating), the ENTIRE store was a sea of pink, and they had ONE rack of boy clothes. I ended up buying something small, and the owner who was checking me out had the nerve to ask if I wanted to sign up to receive their newsletter. I politely smiled and responded, “Why? Do you plan on putting more boys’ clothes in this store?”

The truth is, I love being a boy mom. My boys are so sweet, and I love them to my absolute core. I’ll never forget the days they were born and having their warm precious bodies immediately placed on my chest. All I could do was weep in awe of God’s magnificence and tell them how much I loved them.  

It’s a beautiful feeling and blessing to mother any child mamas. However, if you are a boy mom to be, or have been for a while and are frustrated with boy fashion options, this mama wants to give you hope! The day we were registering for Deuce and saw the minimal options, I became determined that I would not be defeated and subjected to a life of cartoon tees, basketball shorts, and light up tennis shoes! 

I’ve had a blast dressing my boys and have enjoyed putting together their wardrobe. Here’s my full list (and best kept secrets) of how to create a fantastic boy wardrobe so that your little man looks “cool” and not “boring.”

Places to Shop

I learned very early on that you will have to throw all of the traditional stores out the window. Even those that do have “cute” boy clothes tend to result in every boy mom snagging the same thing, so you end up showing up to kids’ birthday parties or a restaurant, and your little guy has on the same outfit as at least one other boy in the room. As women, we know we don’t like this for ourselves, so the same rings true to our offspring, who reflect us!

To find affordable and fashionable boy clothes from 0-5, here are my go-to online and physical shops:

authentically amber how to dress little boys fashion and capsule wardrobe

JCPenney: Did you read that right? Yes, you did! JCPenney! I worked as a marketing strategist there for a few years, and honestly, their exclusive Okie Dokie brand is one of their best-kept secrets! The pieces are affordable, and they have tons of cool shirts with cheeky sayings that I always get compliments on from both men and women. 

Tip: When visiting JCPenney’s website, you’ll need to filter down to the “Okie Dokie” brand to see all of the options; if not, you’ll get tons of pages of very familiar brands that are available anywhere.

H&M: I love the boy styles that H&M has, in addition to their basics. They have a small selection in stores but many options online, so be sure to check their online assortment from cheeky shirts to cool pants and caps. They’ve got a wide variety to help build your “capsule collection,” which I’ll touch on below! 

Tip: I’ve found that H&M sizes can run a bit larger than other brands, be sure to identify what size your little guy wears based on how their sizes run before ordering a ton online. I find that their pants tend to run a bit long.  

Amazon: A few brands via Amazon that I’ve loved and tend to have great boy items. These include:

authentically amber how to dress little boys fashion and capsule wardrobe
  • For swim attire that is fashionable and not cheesy, as well as preppy looks that don’t cost a fortune, my go-to is RuggedButts 
  • Dapper Looks/Special Occasions or photographs Boarnseorl
  • Cute Cheeky Onesies and Rompers with fun sayings Albee Yang
  • Fashionable (and soft) drooly bibs and bandanas KiddyStar here’s a link to one of my favorite eight packs that will help you build your capsule: Kiddy Star 8-Pack
  • Quality classics for special occasions, photographs, etc. Hope & Henry

Hats: I absolutely love Jack & Winn for hats! They tend to have great base colors to go with the styles I’ve put together for the boys, and they also have Daddy & Me options, which I love being able to match both the boys and my husband in the same hats. They are also super comfortable and breathable, and honestly, look cool! Additionally, I love their flexibility, they’ve got a line of Velcro patch hats which allow you to change the patch in the front of your hat to match with whatever style or outfit you’ve got your little guy in. The patches are super affordable which makes it an extremely flexible option. 

Tips on how to get your boys to wear hats

I hear many moms say they can’t get their boys to keep hats on—Here’s how I’ve been able to get my boys to wear hats regularly:

Start them early. By putting hats on them while they are very young – around three months or so, they will get used to them early on, and at that age, they can’t take them off. 

authentically amber how to dress little boys fashion and capsule wardrobe hats

When they get a little older, around 6 or 7 months, and start trying to take the hat off, gently put your hand on their head and say “hat on” after doing that about three times, they should leave it on, even if it’s just for a few minutes. Please continue to do it whenever you put a hat on their head. 

authentically amber how to dress little boys fashion and capsule wardrobe hats

I used to take Deuce to daycare every morning wearing a hat. Even If he took it off once we arrived, it got to a point where he would leave it on the entire car ride, and eventually the whole day, and they would only take it off during nap while at daycare. It’s really a matter of familiarity and something they’ve got to get used to, so the more they have them on and “practice,” the more comfortable they will be in general.

authentically amber how to dress little boys fashion and capsule wardrobe hats

Building his wardrobe & “capsule collection” 

Now that I’ve shared the best places to get affordable and fashionable boys’ clothes, I’ll share what I consider to be the single most crucial thing in really building your boy’s wardrobe and style. It’s what I fondly call my boys’ “capsule collection.” While it’s not a “capsule collection” in the real sense of the word, its how I best describe the strategy I use for building their wardrobes:

  1. Select three base colors. Select a color pallet for a particular season or year. Kids grow fast, so in general, the most we get out of clothes once they hit one is around six months to a year max. Select a color pallet for that particular period. For example, pick three core colors to build the wardrobe and try your best not to deviate. For example, only purchase items that are within that core color pallet or match with it.
  1. Select 3 pairs of shoes, one in each of your three base colors. You’ll want at least two pairs of sneakers, and then one pair of transitional style shoes. I’m a big fan of Vans for several reasons. First, they have base colors that typically align with my color selections for a given season. Second, they are great for little feet and have tons of options with support for first-time walkers with their hard flat bottoms. Lastly, I love opportunities for transitional looks. I recently bought Deuce a pair of black leather vans (See under shoes and accessories). They are technically sneakers, but casual enough that you can dress them up or down.
  1. Select clothing pieces that are either within your core color pallet or blend well with it. 
  1. Get shirts that you can mix and match with different bottoms.
  1. Get pieces you can layer. While I know layering is typically an excellent tip for women, it can also make your little boy look fashionable and stand out. For layering and accessories, I usually include:
  • Hats
  • Lightweight jackets
  • Sunglasses

Now that you’ve got the hang of the basics, here’s an example of planning a season of clothes. Here’s a look at my boys winter wardrobe: 

  • 5 T-shirts
  • 2 Henleys to wear under T-shirts
  • 5 Long-sleeved shirts
  • 2 Pairs of Jeans
  • 3 Pairs of Sweats
  • 2 Pairs of slacks or trousers
  • 1 Heavy coat
  • 1 Hooded sweatshirt
  • 1 Lightweight jacket
authentically amber how to dress little boys fashion and capsule wardrobe

Shoes & Accessories

  • 3 hats
  • 3 pairs of shoes
authentically amber how to dress little boys fashion and capsule wardrobe

Here are some examples: 

authentically amber how to dress little boys fashion and capsule wardrobe
authentically amber how to dress little boys fashion and capsule wardrobe

I hope these tips help and inspire you to have fun with your little boy’s wardrobe. I know there will be a time in the near distant future where I won’t be dressing my boys anymore, and when I’m prepping them for the school year, they will request white t-shirts, basketball shorts, and underwear. I know that time will come, and that’s okay too. In the Bible, Ecclesiastes 3 says there is a time for every season and event under the sun. Embrace this season, mamas. Have fun, dress your boys up, take lots of cool pictures! After all, why should girls have all the fun? 🙂

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  • Reply
    September 25, 2020 at 2:03 am

    I love it. Thanks for the awesome ideas!

  • Reply
    September 25, 2020 at 2:09 am

    Deuce and RG are too cute!!! Best dressed siblings around!!! ??

  • Reply
    Portia Gorman
    September 25, 2020 at 2:12 am

    Aww these photos are giving me all the fashion feels! Thanks for this store recommendation i have two little boys as well!

  • Reply
    September 25, 2020 at 3:08 pm

    I love this. This can even apply to my woredrobe. This will definitely come in handy

  • Reply
    September 25, 2020 at 4:09 pm

    These are some awesome shops and tips! As a mom of a boy it was hard to find shops that captured my sons playful yet stylish style! I actually am obsessed with small shops and my son reps for a number of them! Our fav shops include @cliqqclothing , @triologydesigns @jaxandford / @lennoxjames !!! I have discount codes too so let me know!!

  • Reply
    September 25, 2020 at 8:15 pm

    Oh my gosh, how cute! Now I want a little boy! (I have soon to be 2 ?)

  • Reply
    Robyn Sharpe
    September 26, 2020 at 11:24 am

    I don’t have any boys but I enjoy your blog! Great articles and tips!

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