Monday, November 18, 2013

The 6 Cs of Dressing Little Boys in the Fall/Winter

My sister was in town this weekend so, naturally, we spent some time at the mall.  :)  Jeff and I were incredibly blessed with lots and lots of hand-me-down clothes for Sam's first two years; but, our boy is growing & the hand-me-downs have slowed (my suspicion is that once a boy is two, he is WAY too hard on his clothes to actually get multiple years use of out of them).  As such, this is the first season that we've really had to do any significant shopping for him... NotthatIamcomplaining.

This is a funny stage, because Sam doesn't really fit in baby clothes anymore (even I have given up on the one piece outfits for my 2 year old), but many of the toddler sizes are still too big and/or hideous.  Luckily, I like a good challenge, and (with the help of my mom and sister) was able to find some perfect things for him...

Obviously, the number one C of dressing little boys is CUTE; but, in case you need a little more clear-cut guidance in that area, here are my six staples for dressing a little boy in the fall/winter

Ok, here we go:


First and foremost, I'm going to go ahead and say that the toddler years are some of the last that one can actually pull off wearing sweats in public and call it an "outfit."  So, with that in mind, I'm all about sweat pants this time of year!  And, what better to wear with sweatpants than some kind of fleece or Sherpa-lined top?!?  Duh!!   Aside from these, if there is one thing I will splurge on for Sam its comfy jeans.  We waited a full year to introduce these to our guy's wardrobe, but we don't mess around now... Sam wears jeans most days - to school, to play outside, to run errands, etc., so comfort is really really important.  My very favorite are the knit-waist original fit jeans from Baby Gap because, well, we make it a rule around here to wear elastic waists whenever you possibly can! ;)  (P.S. Hello Gap, can you please start making these in my size?!?!)


From my experience teaching teenage boys and being married to a grown-up man, I think color kind-of gets the shaft in the male wardrobe once they hit a certain age.  Sure, I like a good oatmeal or heather gray or navy as much as the next gal, but I LOVE a little boy in bright colors! I especially like to play with color and plaid/flannel shirts - a favorite of my husband's.  It just seems like the perfect way to add a little "boy" to a big, burly, man look.  You know? There are also LOTS of options for colorful pants out there (see #5) and, you know I've never turned down a striped shirt. ;)


Pretty much if there is a fox or some other woodland creature on it,  we need it.  I just can't get enough.  This is certainly a trend in my own clothing this season, and Sam has not escaped it.  A raccoon going skiing? A bear in a sweater?  I mean, really, who can say no?


I know that dressing your kid in seventeen layers is all the rage these days, but it just seems so darn uncomfortable.  And, while a turtleneck can be adorable when used appropriately, they usually just look dorky most of the time.  So, how's a momma to keep her little guy's neck warm and still looking stylish?  Enter the one button shawl and zip-up collars... Sweater, sweatshirt... oh how I love these!  I think these are just the cutest darn things ever AND they are warm enough with just a simple undershirt beneath them.  Score!


I don't know what it is, but I just think a little boy in corduroys is just about the cutest thing ever. Something about this look is a little more "little" to me than regular old chinos or dress pants, but they still have a sophisticated and durable look to them too.  Plus, is there really anything more adorable than a sweater, cords, and moccasins? Ok, then.
(This is also another great place to have some fun with color.  There are literally cords in every shade!)


Maybe it is different if you have actually have a kid with hair; but, I just adore a little boy in a hat - especially one with ear covers!!  This is the perfect "accessory" for an outfit in my opinion. (Who needs jewelry and handbags?!?)

... And, while we are in the spirit of alliteration, here are three Cs you WON'T see me putting on my boy (yet):

- Characters*
- Camo
- Cross Bones

Like, this, is probably my worst nightmare.  I'm sorry... I.just.can't.

*For full disclosure, I haven't 100% succumbed to the temptation to buy ALL THE THINGS Cars or Thomas related yet; but, I'm probably not all that far away from it... Sam loves those things, and if wearing a shirt with Lighting McQueen plastered across it makes him happy - by golly, who am I to stop him?!?  Luckily, he hasn't really made the connection between his favorite movies and all things commercialized quite yet, but I'm sure it won't be far off.  In the meantime, I won't lie, when I find a cute dinosaur or race car t-shirt (or, better yet, appliqued) at one of my favorite stores, I can't resist knowing how much he will love it (and how much easier it will be to convince him to get dressed in the morning).  I also have to say that many of the big stores like Old Navy, Baby Gap, and even Target have done a super good job lately making even character t-shirts look pretty cool/cute. I think my motto for this will be: everything in moderation.

So, what about you?  How are you dressing your little guy this fall/winter?  What trends do you find yourself drawn to over and over again?  Which ones are you skipping?

(You can see where each item is from my visiting my Polyvore pages here: 1, 2, 3, 4, 5, 6).  

And, by the way, just in case you thought I'm some kind of fancy blogger now that gets paid by major retailers like Target, H&M, Gap, or Old Navy - I assure you, I am NOT.  None of these are sponsored or affiliate links, just some of my favorite places to shop for my favorite little man. :)

P.S. The winner of Pledge FloorCare Prize Pack is SHANNON.  Girl, please email me to claim your prize (you didn't leave an email address in your comment) ASAP! Congrats!


  1. Fun list!!! I am all about color and comfort, too. :) I LOVE dressing Cam like a little man, but some days, sweatpants and a long-sleeve tee are the perfect outfit!! Have a great week!!

  2. This is great!! And that camo/skull & crossbones hoodie...WOW. That's just magical.

  3. LOVE this post! Such great ideas!! I am kindof outside the box with our second one. I want him to have a cute unique style without being all typical boy. (whatever that means haha). I find myself scouring the deal sites or eBay for more unique pieces! Where do you usually shop?

  4. I totally agree with everything you listed! I only wish Sawyer would keep a hat on - he usually only lasts about 20 seconds with something on his head. I also love the layered t-shirt look where it looks like they are wearing a long sleeve shirt under a short sleeve but its really all one piece. Can't stand skull and cross bones either.

  5. I have two girls and I still love this list...especially the critters!

  6. We love those GAP jeans too! I was just telling someone the other day that I HATED camo, characters, and crossbones. Characters are the one thing I'll be lenient on (we might have a cute batman shirt from Old Navy), but please no Thomas!

  7. In the winter, many women try to wear layers of bulky clothing in an effort to keep warm and these are truly cool stuffs for winter season

  8. While searching for a winter coat for Graham, I came across this gem that I know you are sure to love. Cashmere is the C that you left out! I know that Sam will just love it!


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