Adventurous, spirited and f-u-n. These words not only describe the designs and fashions of one of our favorite brands, Cynthia Rowley, but also the namesake designer herself!

Cynthia has gone from Art Institute of Chicago alum to designer, author and creator of a global lifestyle brand. Through her success, Cynthia has continued to remain true to her energetic spirit. And it’s certainly contagious!

Always up for an adventure (and, as we found out, a dare), we caught up with Cynthia and played a quick round of “20 Questions.” Read on to learn some more from the iconic Cynthia Rowley, including her secret talents, pitching ability and surprising thoughts on brunch.


Most worn item in your closet? Cut-off jeans that are about ten-years-old.

Three things every person should have in their wardrobe? See above, plus shoes you LOVE and a sexy dress that you can style a little more conservatively if you have to.

Color you wear the most? Denim.

What book are you currently reading? “Barbarian Days: A Surfing Life” by William Finnegan.

Person you last followed on Instagram? My sixteen-year-old daughter @crybabykit.

Most surprising website you visit on regular basis? My own website, checking in on things.

What is on your nightstand? It’s kinda messy. Notebook and pen, magazines, books, electronics, sleep mask…

Always up for…a dare.

Never up for…brunch!

Favorite dessert? “S’moreos.” I invented roasted marshmallows smooched between an Oreo.

Best gift you have ever received? Robb Pruitt’s painting of a mother and baby panda.

Favorite city in the world? C’mon!? There’s only one!

I never leave the house without…shades

Movie you laughed the hardest during? Triple tie: this weird vampire movie What We Do In The Shadows, Superbad, and Bridesmaids.

Movie you cried the hardest during? Bambi – gets me every time!

A talent or skill you wish you had? Doesn’t everyone wish they could sing like Adele?

The last hobby you picked up? Bass guitar – I’m so into it!

Most random fact about yourself? I threw out the first pitch at a Cubs game and nailed it.

If your life was a song, what would the title be? “Time Of My Life” by Toploader.

Proudest moment of your life? Besides the birth of my own kids… I’m a really good matchmaker and a couple of years ago, friends that I fixed up really DID name their first born child Rowley after me.

Photos by Roger Tully via Tully Productions and @cynthia_rowley on Instagram.