15 Dapper Holiday Shoes & Boots For Baby Boys

There is nothing like a smart pair of shoes or boots on a baby boy. Don’t you agree? They polish off an entire outfit like nothing else.

My son has become quite the fashion plate as of late and if I don’t happen to put his shoes on in the morning he comes running to me with the chosen pair in hand. We recently received a pair of winter boots that are meant to be worn outside, however he has been proudly showing them off while walking around the house.

Luckily nice shoes and adorable styles are not reserved for little girls. Here are 15 of my favourite holiday shoe and boot picks for little guys. I dare you not to “Awww” while going through these adorable picks… ;)

  • Denim Dude

    Denim Dude

    Denim can be dressed up or dressed down and in this case, the shoe is hearing towards the dressier side. Made out of denim fabric, these soft soled shoes are perfect for delicate baby feet.

    Loving the brown button accents on these!

  • Mickey Mouse Loafers

    Mickey Mouse Loafers

    All black, white stitching and a buckled detail make these Holiday Mickey Mouse Loafer Shoes ideal for the holidays. If you check the inside sole you may spot a familiar face ;).

  • Grey Class

    Grey Class

    Clean lines and adorable button details grace these grey pinstripe boots. The lining is made up of fleece and the exterior – soft woven wool. Velcro closures make these easy to take on and off while the button detailing on the sides just add a touch of cute.

  • Tuxedo Crib Shoes

    Tuxedo Crib Shoes

    Nothing says “dress-up” quite like a tuxedo! Each pair of Mini Toes leather shoes are handmade to order using soft leather and natural suede.

  • Caramel Boots

    Caramel Boots

    I’ve got a thing for suede moccasin boots. And with a fringe trim? I’m done! These cuties can be worn with a pair of dressy jeans for a unique holiday look. Warm, stylish and oh so classic!

  • Black Pinstripes

    Black Pinstripes

    These gorgeous soft soled baby shoes for little boys are as handsome as can be. Pinstripes look good with just about everything.

  • Plaid Cuties

    Plaid Cuties

    Made from cotton fabric and lined with felt, these grey plaid soft soled baby shoes are ideal for little boys.

  • Cheery Blue

    Cheery Blue

    Royal blue, playful turquoise and a touch of yellow brighten up your boy’s shoes with these soft crib shoes made up of 100% pure wool felt. The bottoms are lined in non-skid eco leather for a better grip.

  • Brown Suede Shoes

    Brown Suede Shoes


    Your dapper little dude will look so handsome in these brown suede shoes. The laces are made from brown leather cording and the interior is nice and warm lined in a wool blend.

  • Mickey Mouse Stride Rite SRT

    Mickey Mouse Stride Rite SRT

    Shoes that offer a bit of classy and casual elegance are my favourite because they are so versatile. These SRT shoes from Stride Rite are incredibly supportive and have a hidden Mickey surprise! Pull back the velcro closures to say peek-a-boo to everyone’s favourite mouse.

  • Crocheted Baby Boots

    Crocheted Baby Boots

    Can you believe these are handmade? The talent!

    I’ve come across many knitted boots but I definitely think these ones win in the detail department with the cable stitch down the front, wooden buttons and orange and brown trim.

  • Soft Soled Black Dress Shoes

    Soft Soled Black Dress Shoes

    All black, leather and spiffy as can be! The Original Ashton shoes from pediped are a great choice for your boy’s first steps. It certainly doesn’t hurt that they look mighty fine!

  • Preppy


    Is your son more on the preppy side, if so these argyle crib shoes might be a good choice. I’m picturing these paired with a pair of slacks, vest and a bow tie.

  • The Handsome

    The Handsome

    They aren’t really called “The Handsome” but they are so gosh darn handsome I renamed them myself. Stride Rite’s SRT Elliot shoes are perfect for special ocassions. I love the self-molding footbed on these too!

  • Gingham & Grosgrain

    Gingham & Grosgrain

    Vintage with a touch of modern is hard to find these days, but I think I’ve found a pair of shoes that have a touch of both.These white shoes have black and white gingham on the sides and tie up with thin black grosgrain ties.

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