photo DesignProof.png
A Style for Every Story

A style that beckons you to simplicity, adventure & laughter! 

The company features curated collections of women’s apparel and accessories.

We LOVE working with local designers in accessories & fashion!  

Our vision is to create a beautiful space for a lifestyle brand to wander into your life and be a part of your story!!


Jennifer Winebrenner


Creating a beautiful space to discover & inspire is my passion! I have been blessed with leading teams of hundreds of women & interacting with audiences in both the beauty & gift market industries! My experience lies in direct sales and the fashion & entertainment industry! What a pleasure to invite you to experience Ollie & Gray! We would love to serve you!

An entrepreneurial life creates moments to explore & travel with my family! We moved to Charleston, SC in 2016 after traveling to Kiawah Island for 10 years! My son, Oliver, is my heart & sunshine! I’m forever grateful to my husband, Matthew, for his devotion & support especially on creative projects!  

I believe kindness & laughter are two of the best fashion accessories a girl can own - Jennifer