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Preppy Podcast

Patricia Mae Olson
Preppy Podcast
Latest episode

311 episodes

  • Preppy Podcast

    The House of Makeup

    2026/06/09 | 33 mins.
    Crissy Rose McWeeney is the founder of The House of Makeup, a luxury on-location hair and makeup team known for creating elevated beauty experiences for brides, events, and celebrity clientele. In addition to her beauty services, Crissy developed a clean beauty line carried in luxury boutiques nationwide, as well as on Amazon and through The House of Makeup’s online store.
    A true serial entrepreneur, Crissy has expanded her brand beyond beauty into real estate investing, owning sought-after short-term rental properties in both Charleston and the The Hamptons, including @LittleBohoBeachHouse and @SouthamptonHouseNewYork with more on the horizon.
    Before launching her businesses, Crissy built a foundation in both finance and fashion, producing shows during Mercedes-Benz Fashion Week. A lifelong creative with an entrepreneurial spirit, she grew up in the salon industry and developed an early passion for beauty, branding, and hospitality.
    Outside of business, Crissy is an avid world traveler who has explored 55 countries and studied Mandarin in college, experiences that continue to shape her global perspective, aesthetic, and approach to luxury experiences.
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  • Preppy Podcast

    George Cookware

    2026/06/02 | 37 mins.
    Lindi and Anna are the NYC-based sisters behind George Cookware, a brand rooted in decades of steelmaking expertise and a shared love of cooking and hosting. Named after their grandfather George, they set out to create thoughtfully designed kitchen pieces, starting with a baking steel that brings the effect of a wood-fired pizza oven into your home. Today, George Cookware is all about helping people create memorable moments in the kitchen and around the table. Shop at https://www.georgecookware.com/. 
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  • Preppy Podcast

    Kait & Crowne

    2026/05/26 | 46 mins.
    A women's clothing brand where classic British lifestyle meets feminine Charleston elegance. Slow fashion prioritizing natural fibers and ethical sourcing. Learn more at https://www.kaitandcrowne.com/
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  • Preppy Podcast

    Midspring Sport

    2026/05/19 | 50 mins.
    Shannon Arniel and Meredith Carmody are the co-founders of Midspring, a preppy women’s golf and activewear brand designed to bridge the gap between performance and feminine style.
    Best friends since childhood, Shannon and Meredith grew up playing golf together in Connecticut, where their shared love for the game—and frustration with the lack of stylish, flattering women’s golf apparel—sparked the idea for their brand decades later. Their journey spans friendship through school, careers, marriage, and motherhood, all while staying connected through golf.
    Shannon brings deep fashion industry experience, having worked with brands and retailers including Barneys New York, Kate Spade, Evereve and Brandon Maxwell. Meredith contributes a strong background in retail and a lifelong connection to golf as both a family tradition and business networking tool.
    Inspired by the season when golf returns and confidence blooms, Midspring was created to help women feel stylish and empowered from the course to everyday life. 
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  • Preppy Podcast

    Sj Bailey Co.

    2026/05/12 | 45 mins.
    SJ Bailey is an Atlanta-based tastemaker and the founder and designer of SJ Bailey Co., a jewelry brand known for its lightweight, heirloom-inspired earrings. With a background in brand marketing and event planning, she has grown SJ Bailey Co. into a beloved name for brides and special occasions. Through SJ Bailey Curated, she also shares her love of collected interiors, antiques, entertaining, and thoughtful everyday living. Shop at https://sjbaileyco.com/ 
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About Preppy Podcast
The Preppy Podcast features interviews every Tuesday with the brands, businesses and influencers who are keeping the modern preppy lifestyle alive.
Podcast website

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