Packing for little boys shouldn’t be harder than packing for yourself—but somehow, it always is. Whether we’re jetting off for a long weekend or heading overseas, I’ve learned (the hard way) that a well-planned capsule wardrobe makes all the difference. The goal? Pieces they’ll actually wear, that mix and match easily, and that can handle anything from castle tours to ice cream mishaps.
Packing for my boys—now three of them!—has become a bit of an art form. My older two have opinions, preferences, and an uncanny ability to lose socks in hotel rooms. And now with a baby in the mix, I’ve had to fine-tune our travel capsule to be even more streamlined and foolproof. Whether it’s a weekend getaway or a longer adventure, I need pieces that mix and match easily, hold up to all kinds of wear and tear, and keep things looking polished without a fuss.
This capsule wardrobe is our tried-and-true formula: classic basics for play, a few elevated pieces for dinners out, and accessories that make travel smoother (and cuter).
The Building Blocks: Everyday Basics
For comfy, wearable essentials, I always start with Crewcuts and Boden. They strike the perfect balance between cute and durable.
- Crewcuts tees are soft, wash well, and the graphic options are always a hit with my older boys.
- Boden pants and cotton shorts are our go-tos for travel days and active afternoons—they hold up to playgrounds and plane rides alike.
- Add a lightweight crewneck or zip-up hoodie in a neutral for layering (especially handy on chilly flights or in restaurants with too much AC).
For Dressing Up (Without the Drama)
Every trip needs at least one outfit for a nicer dinner or family photos, and La Coqueta is where I always turn for that. Their linen shirts, tailored shorts, and traditional knits are timeless and elevated without being fussy.
I’ll usually pack:
- One button-down shirt
- One pair of smart shorts or trousers
- A lightweight cardigan or pullover for layering
Perfect for: city dinners, church services, or just when you want them to look like little gentlemen.
Accessories & Shoes That Work Hard
We keep it simple but specific when it comes to shoes and extras:
- Hunter Boots for rainy days or countryside exploring (I size up so we can fit thicker socks if needed)
- Nike Jordans for everyday wear—they’re comfy, durable, and pair with everything
- Childrenchic loafers for dressier days (they’re surprisingly wearable and not just for special occasions)
- Classic white socks from Amazon—always packed in bulk
- A few ’47 baseball caps for sun coverage and sibling style points
- A Sézane duffle bag (borrowed from mom!) or State Bags backpack and a carry-on Suitcase
Final Tip: I lay everything out and pack in packing cubes—basics in one, dressy items in another, and accessories in a third. It makes getting dressed on the go so much easier.
You can use this printable checklist to keep it all organized—I’ve got that down to a science by now!
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