Back to School: Our Family Has Loved This Subscription for 5 Years

Getting my daughter's back-to-school wardrobe shopped, sorted, and ready for fall is pretty important business in my home. Penny, now seven years old, lives by a style philosophy where you only get one chance to make a first impression. We have to get it right. Having been through this routine since the preschool days, there is one subscription box that has come to our back-to-school rescue time and time again.

Penny in her kidpik skirt.

Approximately five years and 26 different subscription boxes ago, I had stumbled upon kidpik. I can’t remember how or why exactly they grabbed me as an early subscriber, but the appeal was there, as kidpik kickstarted what would eventually become my consumer fixation. I went in with the best of intentions: to find stylish, comfortable, and affordable clothing for my then-toddler, who was starting preschool and growing at a remarkable speed. Like lots of kids, she emerged from the womb as a pint-sized person armed with a gargantuan personality, and opinions that might as well be regarded as facts. A girly girl type with a keen sense of style, she has been a cheerleader for all things pink and dainty since before she could even walk. Never mind the years I’d spent as a fashion writer or all those runway shows I’d attended during Fashion Week- Penny is the boss of her own style- she knows what’s best for her. And you know what? I kind of love it.

So, we had a gamble on our hands. Perhaps I was naïve, but I’d pictured a situation where a box would arrive, filled with itchy and ill-fitting clothes, wrestling my then-two-year-old into trying on outfits she instantly could not stand. Even worse, in this imaginary scenario, I’d signed a pact with the devil, where the subscription was harder to get out of than a CD mail order club in 1992. “What. Have. I. Done.” I thought to myself. Five years, 47 kidpik boxes, and at least six direct shop orders later, I’ll tell you what I have done in the name of back-to-school shopping.

Ordered the Same Blazer Jacket in 4 Years Worth of Sizes and 2 Colors.

Before you cast me off as some sort of neurotic shopper/weirdo, let it be known that this investment has paid off. As soft as a stuffed bear, more versatile than my go-to LBD, this ‘Ponte’ jacket has been a staple in my daughter’s wardrobe since she was three years old (and she’s seven now, folks!). It instantly dresses up her outfit for any occasion that calls for it and even came to our rescue when she was invited to a last-minute Mary Poppins-themed birthday party. Thanks to the kidpik shop that offers the freedom to buy whatever you want outside of the subscription box, we were able to stock up for years to come. We’re currently on the largest size I’d acquired, and let me tell you, it will be a devastating blow when the inevitable day where she outgrows it arrives.

But Good Things Mustn't Always Come to an End

For now, anyway. There are plenty of wardrobe staples that we’ve collected over the years that are still available for purchase. Do you know how hard it is to find a pair of shoes that your kid doesn’t complain about with every step? Or a dress that takes them from playdate to formal affair, on a tight budget no less? If you’re a parent, you know exactly what I’m talking about. Fortunately, kidpik has kept many of our beloved box finds stocked in the shop.

kidpik Plaid Patch Pocket Skirt - $14.63

When this snazzy cotton plaid skirt arrived in our January 2019 kidpik box, it was an instant hit. This skirt prompted Penny's "plaid phase," and she wore it constantly. Later that year, I went to Scotland and picked her up a genuine tartan kilt, but go figure, she still gravitated toward this one, citing its elastic waist as "more comfortable". Can't argue with that.

kidpik Crinkle Plaid Ruffle Tee - $16.88

Part of what makes kidpik such a smashing hit in my house is the material of the clothes. The quality is great (we've really put this to the test with so many washings), and the clothes are just absurdly soft. This mixed media crew neck was perfect as Penny entered kindergarten in the fall of 2019. Made of 50% polyester, 45% rayon, and 5% spandex, it was super comfortable for her as it offered just the right amount of stretch and temperature regulating properties, thanks to the rayon (because five-year-olds work up a sweat, and Penny considers herself a very busy lady).

kidpik Chiffon Layered Top - $8.75

Looking back on this early 2020 photo of Penny playing with her Oyster box in her go-to chiffon layered top, it's clear I've got a subscription box kid! I'm 99% certain that her jeans are kidpik too, as she's always felt a certain fit freedom to lie down, jump around, and everything in between while wearing them.

kidpik Plaid Knit Jumper - $19.13

Since she was two years old, Penny and I have kept a very special Valentine's Day tradition. Every year, we assemble mini vases of flowers and distribute them to our neighbors (it's kind of a thing now in our building - she gets lovely messages about her flowers for weeks following the holiday!). Here she is in February 2020, waiting for passersby to come through our lobby and accept their annual gift (but really, I think she just wanted them to take notice of her adorable outfit!).

kidpik Classic Patchwork Flounce Top - $9.75

Penny saw zero reasons to slack on style while doing her remote learning. You can see the beaming enthusiasm on my face during our homeschool days, but she actually made the best of the pandemic. This was, after all, an opportunity to showcase multiple outfits between online sessions throughout the day.

kidpik Urban Sandal - $18.38

The pandemic has been hard for us all, and kids in particular, who have missed their friends. In August 2020, Penny's kindergarten teachers organized a socially distant reunion at a local park, and Penny seized this moment to step up her summer chic game. The twist tie top, flowy tiered skirt (a retired version of the Ditsy Floral Skirt), and Urban Sandal shoes... all thanks to her kidpik boxes.

kidpik Ditsy Floral Skirt - $18.83

We've had a couple of these skirts in different patterns over the years, and it is a summer (and spring and fall!) must. It is so precious, I wish they had one in my size! The waist is elastic, so it leaves room to grow. Here she is wearing the skirt to infuse a little fancy to my birthday in August 2020... and almost a whole year later, she's still wearing it like it's the new hot thing.

The $993.46 photo.

The kidpik Dress: $25.50, The Locksmith: $993.46, The Expression On My Face Once I Realized We Were Locked Out: Priceless

It's a pretty good thing that kidpik is as affordable as they are. On my daughter's first day of school in September 2020, she insisted that she wear her favorite kidpik dress. We went outside for maybe twenty seconds to get the obligatory first-day photo. All it took was one swift blow of the wind to lock us out of the house - 15 minutes before school was set to begin - to turn my smile 180º. Twenty minutes and a £718 (approx. $993.46) locksmith bill later, we were back on track. It all worked out in the end though; I'd officially began my journey with the MSA editing team later that day!

More Real-Life Moments, Less Fitting Room Fuss

When I look back on all of these pictures of kidpik outfits from the last five years, what stands out to me are the memories. Every outfit, just like every photo, speaks a thousand words. Happily, being a kidpik subscriber has freed up our downtime, helped us avoid the sort of back to school shopping incidents that department store nightmares are made of, and opened up opportunities to live a more genuine life; the wonderful, the tragic, and everything in between.

Confession time: How do you get ready for back-to-school season? Have you ever had a subscription box that infused special moments into your life? Let me know in the comments because I'd love to hear your stories too!