Simply Blooming Grace

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Many girls dreamed of dressing up like a princess—but what if, as a grown-up, your reality was designing and dressing those very girls? Your passion became reminding them they could express their royalty in everyday life simply by wearing a happy outfit.

A reminder to dreamers that creativity is just a thought away… and that the durability of these clothes would hold up even after a girl rolled down a grassy hill to reach her make-believe kingdom playground.

We were honored to interview a hidden figure—a modern fairy godmother in the fashion world—designer and founder of The Happy Hill, Hillary Roberts.

When asked about her starting point, Roberts shared that she already had some history in entrepreneurship as a boutique owner.

“I started my journey in December 2018 by selling Matilda Jane. After years of being a customer and raising four little ones, I was ready to do something just for me. When Matilda Jane unexpectedly closed in December 2022, I knew I wasn’t ready to let go of the community and creativity I had built around children’s clothing, so I launched my own company—The Happy Hill. At first, I wasn’t sure if I wanted to carry other people’s brands or fully go out on my own, but once I began designing our Signature Collection, everything clicked. I knew this was more than just a boutique—it was the start of a brand with its own voice, style, and purpose,” stated Roberts.

Her reason for stepping into retail traces back to her own childhood of make-believe—just like so many of us once played.

“Honestly, I think my love of dressing little girls started way back with my Cabbage Patch Kids! That joy only grew once I became a stay-at-home mom of four, especially after having my only daughter, Charlotte. From day one, I was obsessed with dressing my little mini-me. I’ve always had a love for color and all things pretty, and that naturally spilled over into how I dressed my kids. I also feel like childhood is moving faster and faster these days, so helping to preserve that sweet, whimsical stage through clothing is something I really treasure.

Starting in the clothing business initially came from a desire to have something for me—something creative, fulfilling, and personal. It was important to me that my kids could be part of it, but that it was also something I could grow and own on my own terms,” said Roberts.

With years under her belt of creating happy memories in the fashion industry, it was hard for Hillary to choose just one—but the moments she did share might flood your heart with happiness too.

“It’s hard to choose just one because there have been so many magical moments along the way. I’ll never forget our very first photoshoot—seeing my designs come to life on actual little girls was surreal. Clicking ‘publish’ on the website and launching that first collection gave me butterflies like nothing else.

But some of the most meaningful moments are quieter—like getting messages from moms thanking me for creating clothes that made their daughters feel special. And honestly, every single time I hear that little cha-ching from a new order, it still brings me joy. That sound is a reminder that someone believes in what I’ve created,” Roberts shared.

For those little girls at heart—now growing up and dreaming of becoming a business owner, fashion designer, or brand creator—Roberts offered a word of encouragement:

“Stick with it—even when it gets hard. There will be moments when it feels overwhelming or uncertain, but pushing through those tough days is where the growth happens. Be authentic to yourself and your vision. It’s easy to get caught up in what others are doing, but your unique voice is what will set your brand apart.

Also, be willing to embrace the learning curve. When you’re building something new, it’s natural to make mistakes or not have it all figured out right away. For me, that meant learning to put my perfectionism aside and just start. Done is often better than perfect—and you can always improve as you go,” stated Roberts.

Of course, we know happy, fashionable fairy godmothers do a lot behind the scenes—but one thing Hillary wished more people understood was the cringeworthy word in business: risk.

“I wish more people understood the amount of risk involved in starting and running your own brand. With every new release, I’m placing inventory orders and holding my breath, hoping that others will love the designs as much as I do. There’s a lot on the line each time—and it never really stops being a leap of faith. But the reward of seeing children wearing and loving something I created makes every risk completely worth it.

It also really challenges my natural people-pleasing tendencies. Even with trusted manufacturers and careful planning, things can go wrong—whether it’s a defect, a delay, or a supply chain hiccup. Navigating those bumps while still providing excellent customer service is something I take seriously. My goal is always for customers to feel cared for and valued, even when we’re working through an issue behind the scenes,” explained Roberts.

Hillary went on to share with us what she loves most about this season of life and her hidden figure work.

“What fills me with the most joy right now is that I get to watch my kids grow up, create timeless, whimsical pieces for others, and live my dreams all at once. I absolutely love being able to design adorable pieces for other children without ever missing a moment with my own. Of course, it’s busy and stressful at times, but it’s also so fun and always bursting with color, creativity, and meaning,” exclaimed Roberts.

This fairytale story isn’t even close to its final chapter. Hopes, dreams, and innovation continue to carry Roberts forward. And what we have to look forward to at The Happy Hill in the future—time will tell. But our wish for a sneak peek at her vision did come true!

“I’m passionate about growing The Happy Hill into a brand that reaches more little ones—and I’d love to eventually make that happen by bringing other moms on board. I would love to expand in a way that empowers women, invites their creativity, and gets our whimsical pieces into more hands. Alongside that, I’m committed to giving back to our community. I want to be able to consistently use a portion of The Happy Hill’s profits to help support organizations and create real, lasting impact in the community,” stated Roberts.

Rachel Redlin is a columnist, author, journalist, and award-winning radio host. She lives in Northwest Kansas with her husband and five children, where she writes about faith, food, and the simple everyday life. Want to read more or contact us? You can subscribe to the FREE newsletter at www.simplybloominggrace.com

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