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Huckleberry Holbrook’s Guide To Dressing Little Boys For The Holidays

Hi guys! My name is Huck. Today, we’re talking about clothes. More specifically, how to dress little boys who are squirrely and don’t like wearing clothes but like looking cute for Christmas cards and Holiday parties and staying warm while out and about in the winter but still being boys and getting dirty and staying comfortable all while making it real easy on you, THE MOMS. Whew! After the jump!

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  • MOM’S NUMBER ONE ADVICE: LAYER 1 of 14
    MOM'S NUMBER ONE ADVICE: LAYER
    Here's real talk: toddlers don't like coats. Coats are our sworn enemy. Don't ask us to wear one. Are you crazy? Instead, LAYER.
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    You can't tell but I have two shirts on under this sweater and I am warm and toasty as could be!
  • MOM’S NUMBER TWO ADVICE: WEAR A HAT 3 of 14
    MOM'S NUMBER TWO ADVICE: WEAR A HAT
    A hat finishes off any outfit for a boy, and covers bedhead too cause let's face it, boys get bedhead. Nothing is more festive than a good hat.
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    image-665
    ESPECIALLY not a ski hat.
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    image-667
    Look at me! This could be your Christmas card photo! Jingle bells and stuff!
  • MOM’S NUMBER THREE ADVICE: MIX PATTERNS 6 of 14
    MOM'S NUMBER THREE ADVICE: MIX PATTERNS
    See, this outfit is a Mom Classic (TM). I got my stripes, I got my even more stripes, I got my solids, I got my fair isle. I look like a million bucks. For pictures, this is an especially good look because it creates dimension and texture and lots of visual interest. Plus, like we already discussed, I'm ready for a blizzard in this outfit! Not even cold one bit!
  • MOM’S NUMBER FOUR ADVICE: RED BUFFALO CHECKS 7 of 14
    MOM'S NUMBER FOUR ADVICE: RED BUFFALO CHECKS
    Buffalo checks are just as good during the fall and winter holidays as they are during the summer picnic months. With a long sleeved layer underneath, this shirt is perfect for Thanksgiving dinner. Without the tee and with the sleeves rolled up, I'm all set for a Sunday summertime picnic. This shirt will last me all year long!
  • MOM’S NUMBER FIVE ADVICE: HOODIES 8 of 14
    MOM'S NUMBER FIVE ADVICE: HOODIES
    Hoodies are a classic way to dress your boys that's just a little bit rough and tumble and spirited. The best news is, if I refuse a hat and it's chilly, she can pop the hood up and there's no way I can toss it over the stroller when she's not looking (at least not without tossing myself over too, hello laws of physics!).
  • MOM’S NUMBER SIX ADVICE: STRIPES 9 of 14
    MOM'S NUMBER SIX ADVICE: STRIPES
    Stripes are good for the holidays and they're good for all the days, and they make for a great layering piece. This striped top is a onesie, and it's our go-to traveling layer, since it stays tucked in and helps keep my belly warm. I always look cute in my stripes because they're a classic and they hide food smears real good. Food smears and boys are pretty inevitable, right?
  • MOM’S NUMBER SEVEN ADVICE: MOCCASSINS 10 of 14
    MOM'S NUMBER SEVEN ADVICE: MOCCASSINS
    Moccs are great because they match with EVERYTHING, and these ones especially, made by Freshly Picked, go on easy and stay on easy and are perfect for beginning walkers. No kidding I wear these shoes every day, except for Saltwater Sandal days in the summer when it's too hot for closed-toe shoes.
  • MOM’S NUMBER EIGHT ADVICE: RED PANTS 11 of 14
    MOM'S NUMBER EIGHT ADVICE: RED PANTS
    Red is festive. It also matches everything, by virtue of the fact that it is LOUD and tends to bring out the fun side of any top. Can you check out our complimentary patterns by the way? I mean...
  • MOM’S NUMBER NINE ADVICE: CARDIGANS 12 of 14
    MOM'S NUMBER NINE ADVICE: CARDIGANS
    This is Mom's big sell: If you're going to buy anything, ANYTHING for your baby boy, make it a gray cardigan. It'll go with everything and instantly dress up even the silliest Snoopy tee. I look like I'm ready for a funeral, or a party, or church, or Christmas dinner, huh! I know it! (This photo was taken earlier this year, and it makes Mom get misty-eyed. I was sooo cute!)
  • MOM’S NUMBER TEN ADVICE: STICK WITH THE CLASSICS 13 of 14
    MOM'S NUMBER TEN ADVICE: STICK WITH THE CLASSICS
    When in doubt, classics like baseball tees will always look good in photos (neon yellow baseball tees? sure!) so keep that in mind when stocking up on kids basics. Avoid too many logos or trendy cartoon characters and your tot will always look ready for a family gathering and photos at the end.
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    image-669
    Till next week, thanks for reading, guys!
    Love,
    Huck

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