Featured, Society & People

Brands that Rock: Tipsy Skipper

If you love Lilly Pulitzer, Vineyard Vines, J. Crew, and other preppy patterns (and let’s be serious, many, many BC girls do), you need to check out Tipsy Skipper. I recently heard about this brand and was immediately excited to hear that the founder, Kearsley Lloyd, is an alumnus of my high school, Tabor Academy. I was even more excited when I looked at the website and fell in love with what I found. After telling my friends about it, I couldn’t help emailing Kearsley to ask if I could feature her brand on The Rock. KAL_boat2

It seems as though Kearsley was destined for this career. She grew up by the ocean in Rhode Island where she spent her childhood sailing and drawing. After spending four years at Tabor Academy, a high school located on Buzzard’s Bay in Massachusetts, she attended Rhode Island School of Design. I was surprised to hear that Kearsley was a bit of a “black sheep” at RISD; while many other students had piercings, dyed hair, and artsy tattoos, she preferred wearing pink and pearls. Kearsley interned with different designers, such as Vineyard Vines and Lilly Pulitzer, which influenced her gorgeous, playful designs. Throughout her four years as a graphic design major, she decided to combine her passion for art and design with her love for preppy patterns. With this in mind, she designed a line of accessories for her senior project and, as a result, the Tipsy Skipper was born.

“New England – and its extraordinary beauty – has had a tremendous impact upon my artistic identity,” Kearsley says. Many of the patterns are nautical and summery, yet still perfect year-round. As the winter drags on and I grow tired of brown and black sweaters and boots, nothing makes me happier than shopping online for spring break and summer accessories, and Tipsy Skipper offers just what I’m looking for. Currently, after just two years of business, the Tipsy Skipper offers a wide range of clutches, tote bags, shoes, and jewelry. The prices range from $12 to over $100, making the Tipsy Skipper a great place to shop for a little gift or a bit of a splurge. In the future, Kearsley hopes to expand and even start a men’s line. Further, she does custom designs for different schools, hotels, and sororities. I can already imagine a BC maroon and gold “Captain Morgan Clutch”!

photo by Connerton Photography
photo by Connerton Photography

One aspect of the website that really appeals to me is the link to the Tipsy Skipper blog. Here, you can read updates and browse through various outfit ideas. The ensembles are an adorable, perfect cure for winter blues. And not only are the products beautiful, but Kearsley’s story is truly inspiring. She has taken her artistic talents, her love for New England and the ocean, and her sweet, bubbly personality to create her very own brand and business. Tipsy Skipper is a breath of fresh, summer air and I can’t wait to see how it expands in the future!


  1. This is awesome! Just checked out her site – so many cute things! I love that the custom clutches with monograms are either the same price as the other clutches or only a tiny bit more. Love the personal touch!

  2. Tipsy Skipper looks like a great new entry into the preppy fashion world. I will definately be adding a tote bag in the near future.

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