Tips for Dressing Toddler Boys This Summer

I invited my very good friend, Sharon of NYC Taught Me, over here today to share her tips for dressing toddler boys. She has twins the same age as Henry and they always look super stylish (evidenced by the photos below. That cut-offs outfit KILLS ME!). Sharon and I hung out practically everyday when she lived here in San Francisco until she left us for New York City last Fall (yes, I still cry about it everyday). I love to follow her exciting Manhattan life and get toddler dressing tips on her fun blog, NYC Taught Me. Welcome, Sharon!

I’m pretty good at dressing my daughter, mediocre at dressing myself, but my twin boys? I’ve got that down. Here’s my summer tips for dressing boys. Thanks for letting me guest post Liz!

  1. Look towards mens fashion for ideas. Right now I’m seeing a lot of men wear V-neck t-shirts and cut off shorts. Perfect for toddler boys too, right? You can find v-neck shirts here and cut-off shorts here
  2. Accept hand me down clothes from friends, but edit. I was once the lucky winner of 3 garbage bags of used clothes from a generous neighbor. The clothes were clean, lightly used, but the fit wasn’t quit right.  I kept a few pieces and shamelessly donated most of it to charity.  
  3. Buy gender neutral clothes in girls department. A lot of times boys clothes are too baggy. I swear by the girl jeans from H&M, these girl shorts from Crazy 8, and these pants from Target (trust me on this one).
  4. Repeat Repeat Repeat outfits. It’s green, it European, it makes your life easier. My boys repeat the same outfit for days until it fails the smell inspection and until the stains are large enough to be spotted on camera.  
  5. Splurge Once! Buy a piece of clothing you know is totally over priced but you love it. I bought these light sweaters for my boys for spring. This summer’s spurge: these shorts
  6. Look in unexpected placesCVS Pharmacy has really cool sunglasses for boys this summer.  
  7. SUSPENDERS! Everyday!  

    See, isn’t she awesome? Headed out to buy suspenders asap. What do you think? Do you like dressing your boys like little men? Think you could swing any of these looks on your toddler boy? Should we really trust her on those black leggings from Target?
    Thanks Sharon!


    with an eight month old boy, I love this post! can't wait to dress my little guy in the coming months.

    my super picky son loves his black stretchies! he rocks the skinnys with hi-top converse and a t-shirt. it is such a cute and comfy look and his tush in those pants!!! adorable!

    unfortunately my girls dont even enjoy the girls section *sigh* all of my daughters can not stand jeans/jean shorts (too tight, push into your belly when you sit down, annoying zip and button.. and the list goes on) they cant layer (hurts your armpits) oh I dream of having fashionable kids….these looks are mega cute if you can pull them off.. and I almost agree on the legging thing. They would be more comfortable, easy to move around in, but look like black pants?? why not! smart thinking.

    I have two-year-old twin boys and love these tips, especially the one about buying girl's jeans. I've actually been feeling guilty about dressing my boys in some hand-me-down girl's jeans, but no more!!

    this is genius, love her new contributor. I hope she comes back alot

    Thanks for the tips! I love dressing kids like little mens ;)Suspenders? Love how cute but cool they look 😉

    i always buy my boys jeans from the girls section too! you just have to be careful about any flowers/pink details…

    I love your this week's post. Its really intersting. I love the boys dressing style. And it looks soo cool.

    boys totally get the shaft, these are great ideas. I can visualize the black pants and they'd look great i think. excited to give it a try

    these are all really cute, but they don't look all that comfy. My boy is picky about his clothes and always prefers comfort.

    Omg i LOVE this post and I LOVE the suspenders idea!

    Hahaha I'm in love with the suspenders!- Sarah

    i love those suspenders but there's no way i'd end up styling them cute. they'd probably come off before we left the house.

    i LOVE how she dresses her boys! i agree that most boy jeans are way too baggy, and i love those american apparel cardigans; totally unisex and they seem to last a long time, size-wise. my daughter wears them and i'll be saving them for when my son is big enough.

    This is awesome – I have such a hard time figuring out little boy style (girls are easy – just throw on a dress in summer!). Thanks for the tips!

    oh my goodness these little boys are so cute! They look so stylish I cant believe it! The suspenders are just too cute for words!

    I'm not a fan of the 'men dressed in women's clothing' look either, so I think girls jeans for boys is pretty ridiculous. But I do like the idea of looking to men's fashion for ideas in dressing toddler boys. I love a little boy dressed like a man! (And I cringe at the number of puppy dog and dump truck motifs on little boy clothes) But I like men who dress like men – not girls.

    I LOVEEEE this outfits!!! Did that say enough?PS: don't forget this giveaway end today.

    with 3 boys, i LOVE this post. boys get the shaft when it comes to retail space and creative design. makes us moms work a little harder to dress our little dudes well.

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