Written by Cassidy Eisenfeld | Mom of 4 | Certified Babywearing Educator

As a mom to four little ones and a certified babywearing educator, I’ve learned a lot—both through hands-on experience and through helping hundreds of other families feel more confident and connected. Babywearing has carried me (literally and emotionally) through some of the hardest, sweetest, and most transformative parenting moments. And I want to pass that support on to you.

Whether you're in the thick of the newborn haze, figuring out how to nurse on the go, or wondering if wearing your toddler is still worth the effort—this post is for you.

Breastfeeding in the Carrier: What I Wish I Knew Sooner

Breastfeeding while babywearing can feel like a magic trick at first—but once you get the hang of it, it’s one of the most freeing tools in your parenting toolkit.

Here’s the truth: it doesn’t have to be perfect, just safe. You don’t need to master hands-free nursing on day one (and you probably shouldn’t!) Start small. Learn how to loosen your carrier just enough for baby to drop to breast level, and make sure baby’s airway stays clear the entire time. Upright feeding is most commonly best practice and also a win for babies with reflux or those who need a little extra snuggle support while eating.

Slings, stretchy wraps, and some soft structured carriers (like LennyLamb, Sandiia, or Tula) can all work for feeding on the go—you just have to learn the mechanics of your setup. My advice? Practice at home, when baby isn’t overly hungry, and you’re not already stressed. And remember, it’s okay to pause, reset, and try again later. You’re both learning.

Newborn Safety Tips: Start Strong from the First Snuggle

Wearing a newborn can feel intimidating—and that’s totally normal. But the key is to remember a few core principles: clear airway, snug fit, and supported spine.

Look for a carrier that:

  • Supports baby’s natural "froggy" or M-shape positioning (knees above bum, back rounded) This will almost always be with legs outside of the carrier.

  • Keeps baby close enough to kiss

  • Allows you to see their face at all times (no fabric coming up over the head)

  • Feels snug, like a gentle hug (no slumping!)

Avoid anything too bulky or loose in the first few months. I personally love soft wraps or ring slings for those early days—they mold to baby’s body, support their development, and keep them feeling safe. It’s not just about convenience—it’s about meeting their need for closeness in the most primal and profound way.

Wearing Your Toddler: Yes, It’s Still Worth It

Let’s be honest: toddlers are wild little forces of nature. But they’re also still deeply in need of connection, co-regulation, and rest—and babywearing can offer all of that.

Wearing a toddler:

  • Helps during transitions (travel, nap times, crowded spaces)

  • Offers emotional regulation (they’re still learning how to process big feelings)

  • Frees up your hands when you have more than one child in tow

  • Supports bonding during challenging phases

My own toddlers have been worn on hikes, through airports, and while I cooked dinner with a baby on the back. The weight shifts. The needs change. But the benefits? They just deepen.

Look for a toddler-size or adjustable carrier that offers strong lumbar support and wide shoulder straps. And remember—just because they can walk doesn’t mean they don’t still need to be carried from time to time.

You’re Doing Great

It’s easy to get overwhelmed by all the options, advice, and expectations around babywearing and breastfeeding. But at the end of the day, this is about you and your baby (or toddler). It’s about what works for your body, your family, your rhythm.

There’s no one-size-fits-all answer—but there are tools, support, and a whole lot of love available to help guide you. If you’re unsure where to start, come hang out with me at @letstalkbabywearing or explore my guides and community support at letstalkbabywearing.com.

You don’t have to figure it all out alone. You’re already doing the most important thing—showing up.

Courtney Boylan