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A Style for Every Story

Our vision is to create a beautiful space for a lifestyle brand to wander into her life!

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

The company features curated collections of women’s apparel for the selective client.

Our unique focus on creativity & StyleBar opportunity brings alive the entrepreneur’s soul!

We have thought of her with every detail!


Jennifer Winebrenner

JENNIFER WINEBRENNER, Owner

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! I am honored to be a part of this creation and look forward to hearing your stories!

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!  - Jennifer