Strollers and Heels- Yay or Nay?

Prior to having River my cup runeth over. AKA my closet was stacked with heels. It was something I was quite proud of. Upon walking into my pre-baby apartment, a nice red pair of six inch heels were there to greet you accordingly. A badge of honor if you will.

Alas, here I am! 2 1/2 years into motherhood, and I reminisce fondly of those days. The days of heels without care or mommy judgement. Don’t get me wrong, I am in no way missing out. Some six inch heels are still there,  waiting to be dusted off on the occasional date night. Others, do actually see the light of day more times than I would have predicted some years ago. And some are gone, gone with cropped tops and short shorts (I’m sure I will get to that in later post soon enough).

With anything in this whole motherhood thing, deciding to rock a killer pair of heels with a stroller in tow is a balancing act. And frankly, takes some good ol’ confidence. You have to find the perfect stroller friendly heels. Ones that feel sexy, but most importantly safe.

If you ask me, and if you’ve seen me around, then you know I think rocking a pair of heels with a stroller is a total… yay!

  • River and I 1 of 7
    Wedge sneakers count as heels too! ;)

    Some may disagree but I consider wedged sneakers a heel. Yes, they are very comfortable, but they still add a chunk of height.We love our urban stroller, and I think my urban wedged sneakers are killing it. And that bridge!!!

    P.S I am totally biased.  

  • Natalie and Huck 2 of 7
    Natalie's boots are the perfect blend of comfort, safety, and height.

    Natalie's boots are a New York City girl's dream. They give her a little bit of height, but they also aren't so high that she towers over Henry's stroller. 

  • Belle 3 of 7
    Belle's boots, are perfect for her height and for her stroller. The thicker heel balances out her beautiful tall frame, all the while letting her meet firmly with her stroller handles.

    Belle's boots are even more amazing in person! I love that the thickness of her heel compliments the tires of the stroller. I know that sounds weird, but it does! It all blends so well. 

    photo via

  • Flee market heels 4 of 7
    I've found that on rainy Saturdays I am even more compelled to throw some heels (wedges) on. There's something about pushing a stroller when it's a crappy day and NEEDING to feel just a tad bit cute.

    A rainy Saturday flee market win. I just threw a pair on and I suddenly felt like I actually tried looking decent. 

  • Natalie Again! 5 of 7
    Heels on a sunny day, heels on a rainy day. Love that these aren't too high, aren't too low... but just right.

    Natalie and baby Henry too! Natalie is openly addicted to heels (me too, me too). I think she's one of the many people who has the heel and stroller balance down. You go girl!

    Photo via

  • Clogs and strollers 6 of 7
    Clogs under the bridge

    Same spot as the first photo, but different shoes! I am such a fan of clogs. But even more so of clogs and strollers in the same picture! Together it sounds like a pretty boring combination, but on, they look effortlessly chic. 

  • Casi 7 of 7

    Fierce, just FIERCE. 

    Photo via Casi of CupcakeMag

Tip: you can always throw a pair of flats in the stroller basket for safe measure. 😉


You can find more personal style tips, thoughts on city life, and cute toddler pictures over on LaTonya’s blog.

And if you dare, even more on her instagram (@latonyayvette)

Article Posted 3 years Ago
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