Preppy Rainy Day Outfits

Yellow Hunter Boots / Yellow Barbour Rain Coat / Emma’s Yellow Rain Coat / Emma’s Ralph Lauren Dress / Emma’s L.L.Bean Boots / Emma’s Bear Tights

Happy May!

I’m always missing “big events” by a day or so. 😂 But I can’t express how excited I am for this month! There’s just so much occurring for my family, and I’m really excited to share our next chapter with you.

Anyway, it’s been raining here in Chicago for the better part of the past week, and it’s not showing many signs of letting up. Things are one big, soggy mess. But I published this little “perspective piece” the other day on Instagram, and thought I’d share it on the blog, too. :)


When faced with rainy days, adults tend to feel glum. Kids, though, usually look at the rain differently.

They see something extraordinary; something that makes the day rare and therefore significant and memorable. They happily splash through puddles, delight in their “special occasion” foot and outerwear, wonder what kind of exciting changes will be made to their schedules, and marvel at the functionality of their miniature umbrellas that they carry with great pride. There is magic in these days.⁣

I want this outlook, not just on the rain but on life as well. Far too often, I subconsciously think of rainy days–both the literal and figurative–as days that I just need to make it through. In my mind, they’re the only roadblock that stand between me and *great* times. But the extraordinary moments, big and small, have occurred during wonderful and tougher streches alike… and I wouldn’t want to give up any of them.⁣⁣

Scoring my first field hockey goal when I was also going through my first heartbreak; a long walk with friends on the Sound during my best year at Fairfield University; attending a concert during a thunderstorm in Central Park; falling in love with Mitch while broke and floundering in NYC; watching the fireworks explode over the sky in Chicago and thinking about how everything was starting to fall into place; running through the leaves during a hellish work season; finally meeting my little girl after so much uncertainty and fear; watching the sun sink into the sea with Mitch’s arms around me and Emma at my feet.⁣

All random moments that flitted through my mind just now, but all awesome ones that occurred during lots of different types of “weather.”

So let’s stop thinking of the rain as something we simply need to get past. Instead, let’s look at it just as kids do: as something extraordinary, significant and memorable… and that has to power to produce magic. After all, it’s the rain that makes us truly appreciate that which is special.⁣⁣

And when this outlook fails us–because it undoubtedly will–let’s just stomp in the puddles and delight in our special occasion footwear, which is pretty darn fabulous, too. 😉

Flowers - Springtime
Emma Larkin is wearing a rainy day outfit
Toddler Preppy Rainy Day Outfit
April Showers
April Showers & Preppy Rainy Day Outfit
Yellow Rainy Day Outfit
Toddler Rainy Day Outfit
April Showers - Kelly in the City
April Showers on the blog

Shop the post:

Yellow Hunter Boots / Yellow Barbour Rain Coat / Emma’s Yellow Rain Coat / Emma’s Ralph Lauren Dress / Emma’s L.L.Bean Boots / Emma’s Bear Tights