I once challenged myself to buy some clothing for a friend’s baby girl and quickly felt helpless surrounded by so many pink and purple ruffles and flowers. In that moment, I felt grateful I had a boy at home to dress.

With far fewer choices, shopping for boy clothing is easier, but it’s not without its challenges. The little boy department is typically filled with clothing in dark or primary colors, many emblazoned with sports-themed graphics, anthropomorphized trains and trucks, and cutesy sayings like “Mommy’s special this” or “Daddy’s little that” — all of which are very stereotypical of preschool-age boys.

There are also usually a handful of clothing items featuring skulls and crossbones, which I don’t necessary think are appropriate for young boys. Unless the design has something to do with pirates, I don’t need my toddler dressing up as a little punk.

In the two years, I’ve honed my shopping skills for toddler boy clothing. I can briskly browse the boys department and determine whether there’s anything worthwhile. Some people may call me picky. I guess I can’t really argue with that! But is it so wrong that I want Levi to dress like a kid — not a baby, not a grown up — in comfortable, stylish, non-stereotypically boyish clothing?

Here’s how I like to dress a toddler boy:

Tops: When shopping for shirts, I usually reach for solids or all-over patterns like stripes, color blocking, or plaid. Levi is a big fan of stripes! Robot and outer space prints are a hit in our house, too.

I also try to look for vintage-inspired, hand-drawn, or gender-neutral designs. Luckily, I’ve found several brands that do this really well, including Winter Water Factory. I love that their illustrations are bold with a child-like whimsy.

Pants: Because Levi is so slender, skinny or straight-leg jeans and pants look best on him. (Confession: I used to buy him pants from the girls department!) I know that patterned leggings are trendy for toddler boys right now, but I’m honestly not sure how to style them. Levi’s pants are all solid colors, but I don’t shy away from bright hues like coral, teal, or even mustard yellow.

Socks: Until recently, Levi only wore solid white socks because I didn’t have to worry about mismatched pairs. (Toddler socks are notoriously easy to lose in the laundry.) But my mom bought Levi a pair of orange socks with black pumpkins for Halloween and he’s obsessed with them, so now I’m starting to look for more fun patterned socks.

Shoes: Levi’s feet are too chubby for slip-ons, and I honestly don’t want to have to untie/tie laces every time we change a diaper or try going potty. Velcro works best for us, and I love the look of old-school running sneakers on Levi’s fat little feet.

Levi’s wardrobe is small. He tends to go through all of his pants within a week, and we repeat many of his outfits. Although I don’t mind investing in a few better quality pieces that I know will survive multiple launderings, I try not to overbuy or overspend because Levi will outgrow or stain them…usually sooner rather than later!

Are you choosy about what your toddler wears? Would you say he has a particular style (preppy, hipster, athletic) yet? 

This post was brought to you in partnership with Winter Water Factory. Follow them on Pinterest and Twitter for more toddler style inspiration. All opinions are my own. Thanks for supporting the sponsors that allow me to create new content for Bunny & Dolly.