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!
- 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.
- 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.
- 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).
- 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.
- 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.
- Look in unexpected places. CVS Pharmacy has really cool sunglasses for boys this summer.
- 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!

