Preppy Podcast

40 Episodes
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By: Patricia Mae Olson

The Preppy Podcast features interviews every Tuesday with the brands, businesses and influencers who are keeping the modern preppy lifestyle alive. 

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Laura Dunn
Today at 9:00 AM

Laura Dunn is an acrylic painter and mixed media artist based on St. Simons Island, Georgia, where she lives with her husband and their 2 young children. 

As a child, Laura grew up inside commercial greenhouses, her family’s business. Her earliest memories are of flowers that she examined at eye level and being completely surrounded by hanging ferns. This perspective has stayed with her and is the reason she captures blooms and foliage up close. The exhilaration of being enveloped by ferns or examining buds and blooms up close is imprinted in her memory.<...


Easkey Right
10/20/2026

Easkey Right is a female-founded, coastal lifestyle and accessories brand created by friends Ashley and Sara. Inspired by summers on the water - Ashley in Ocean City, New Jersey, and Sara on Cape Cod, Massachusetts - the duo connected while raising their families in the seaside town of Scituate, Massachusetts. Combining Ashley’s background in product retail sales and Sara’s expertise in marketing and advertising, they merged their corporate experience with a shared design aesthetic and a passion for neon. The resulting collection blends East Coast roots with West Coast vibes. Built around nautical tradition, Easkey Right weaves mari...


Lindry Lab
10/13/2026

Lindry Lab set out to create the best fabric and home care products without compromise. Unlike other detergents and cleaning products Lindry Lab checks off all 3 pillars of formula fragrance and packaging-without compromising quality, ingredients, safety and social responsibility. Shop at https://lindrylab.com/ 

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The Fancy Society
10/06/2026

Adjani is the founder and creative behind Fancy Society, a colorful, handmade jewelry brand started in Jacksonville, Florida, in 2019. Obsessed with color, specifically pink!, sparkle, and making everyday life feel a little more fancy. Fancy Society is really about celebrating the fun things in life, being unapologetically yourself, and wearing the statement jewelry. Shop at https://thefancysociety.com

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Pastel Proper
09/29/2026

Pastel Proper began in 2022 with a simple idea: the places we love deserve something more personal than a souvenir and more lasting than a photo on a phone. Our signature blank books were created to give those places a home. Designed to be displayed, gifted, and filled over time, each one becomes a place for handwritten notes, guest signatures, photos, inside jokes, family traditions, and the little details that make a destination feel yours. In October 2025, friends Eleanor and Marie took ownership of Pastel Proper, bringing together their love of interiors and backgrounds in design, retail, and consulting. Today...


Marfa Boots
09/22/2026

Brooke John is the owner and designer of Marfa Boots. Started in October of 2022 in Dallas, Texas. The inspiration for Marfa Boots came when attending the American Rodeo and couldn’t find a pair of boots that would stand out from the crowd without breaking the bank. She realized there was a need for a brand of boots that is trendy, affordable, and can pair with a variety of looks. They have worked tirelessly to design and create a line of boots we believe to be a centerpiece in everyone's wardrobe. Shop at https://marfabootsco.com/ 

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Ink + Alloy
09/15/2026

Gretchen Hollingsworth is a serial entrepreneur who built Paddywax into an internationally recognized candle brand before selling it in 2015 and turning her attention to her next chapter. She launched INK+ALLOY in 2016 — a handmade accessories brand designed in Atlanta and brought to life by skilled artisan women in India, now beloved in boutiques across the country. Purpose-driven from the start, INK+ALLOY  partners with Commit 2 Change to fund education for girls in India — giving back to the community that inspires every piece INK+ALLOY makes. Shop at https://inkalloy.com/ 

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Allie+Bess
09/08/2026

Allie+Bess is beaded jewelry made for living in color! Located in Dallas, Texas and founded by best friends and business partners Allie Wardlaw and Bess Callarman. Shop at https://shopalliebess.com/ 

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LBS Designs
09/01/2026

Lalania Balas is the founder of LBS Designs, creating hand painted canvas totes and Italian silk scarves inspired by the places we love and the places we want to go.

Her career began in New York City’s Garment Center, spanning fashion, product development and accessories companies including Daniel Wellington, where she worked with early influencer programs and brand partnerships. She later moved into talent management in Los Angeles, helping influencers translate their personal brands into product.

Covid took her to Boca Grande to hide out with family and recharge. A longtime boat & tote girl fr...


Hey Friends
08/25/2026

Shaefer Santos is the founder and designer behind Hey Friends, a women's clothing brand inspired by timeless coastal style and thoughtful design. She started sewing and designing clothes as a little girl, and what began as a hobby eventually turned into the business she runs today. She launched Hey Friends when she was 16, and today she designs every collection with the goal of creating beautiful, wearable pieces that women can reach for season after season. Whether she is sketching new designs, working with artisans, or sharing the behind-the-scenes journey of building the brand, her heart has always been in...


Mahj
08/18/2026

Thirty years ago, Kathy Wise learned to play mahjong from a friend's Jewish grandmother while she was a law student at The Ohio State University (Go Bucks!). She spent a decade as a litigator before deciding to pursue her original passion, magazines. In 2016, she joined D Magazine, where she currently serves as editorial director. Under her leadership, the magazine has won numerous national awards, including CRMA awards for General Excellence and Excellence in Writing. Kathy has personally won a CRMA Award for reporting for “The Most Lawless County in Texas,” a feature about a Collin County judge who was conv...


Cuvée Home
08/11/2026

Bailey Ward is an Atlanta-based interior designer, founder of Cuvée Home, and the creative force behind the brand's thoughtfully curated collection of lighting and home décor. With over a decade of design experience and a degree in interior design, Bailey brings a refined eye for detail, craftsmanship, and functionality to every project and product she creates.

Guided by a designer's perspective, Bailey personally leads the design and curation process for Cuvée Home. Inspired by global interiors, timeless craftsmanship, rich layers, bold color, and the interplay of pattern and texture, she founded the brand to fil...


Vietri
08/04/2026

When Susan, Frances, and their mother, Lee Gravely, took their first trip to Italy in 1983, they fell in love with the Italian culture. Thus, a brand was born that started with Campagna, VIETRI's flagship dinnerware. Throughout the years, VIETRI's focus has been to celebrate the simple act of sharing a meal with family and friends. Inspired by the Italian lifestyle, VIETRI encourages savoring one another's company, and keeping sacred the time spent around the table. Learn more at https://www.vietri.com/

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Love All
07/29/2026

Love All is a family of classic, vintage-inspired sportswear brands designed for real life: on the court, on the course, on the slopes, in the water, and everywhere in between. They believe sports should feel joyful, flattering, and accessible at every stage of life.
From tennis whites to ski knits, swimsuits to aprÚs layers, Love All blends heritage style with modern performance fabrics, creating pieces that move with you and live beautifully beyond the game. Shop at https://loveall.com/. 

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WanderFull Brand
07/21/2026

Stay hydrated and never forget or lose your expensive reusable water bottles with this stylish water bottle bag. Shop at https://wanderfullbrand.com

Use code PreppyPod for 20% off. 

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Nattie Golf
07/14/2026

Nathalie Sheehan offers refined golf instruction, curated golf lifestyle inspiration, and timeless style for women. Rooted in the traditions of golf and expressed through a modern feminine lens, it celebrates the sport not only as a game to be played, but as a way of living. Through refined instruction and an authentic female perspective, Nathalie invites more women to experience the game with confidence, clarity, and ease. Discover more at https://www.nattiegolf.com/. 

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Chassity Evans
07/07/2026

Chassity Evans is a content creator sharing finds in fashion, home decor, beauty, and wellness. She’s a romance author with her debut beach romcom novel, Pink Sand Summer, set in Harbour Island, The Bahamas, where she owns a home called Coral House. Discover more at https://chassityevans.com/

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Lippa
06/30/2026

Beeswax lip balm is designed to heal dry, cracked lips while providing deep, lasting moisture so your lips stay healthy, not just temporarily relieved. Shop at https://lippaskincare.com/ 

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York Design Co
06/23/2026

Modern heirloom needlepoint Hand-stitched cuffs, keychains, accessories with small batch drops in support of pediatric cancer research. Shop at https://www.yorkdesignco.com

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Elisamama
06/16/2026

Elisamama is a vibrant, women-led apparel brand known for joyful, easy-to-wear clothing featuring joyful colors and traditional African Ankara prints. Founded by Fisayo Che, all pieces are handmade by local artisans in Nigeria to support economic empowerment, and focus on functional, stylish silhouettes. Shop at https://elisamama.com/ 

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The House of Makeup
06/09/2026

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.

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George Cookware
06/02/2026

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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Kait & Crowne
05/26/2026

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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Midspring Sport
05/19/2026

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 reta...


Sj Bailey Co.
05/12/2026

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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Fete & Vignette
05/05/2026

FĂȘte & Vignette was created to be Birmingham's go-to source for tabletop event rentals, styling, florals, and decorative accents designed to elevate everyday and occasions. We offer curated rentals to make your events unforgettable and hosting more effortless. 

Founded by Dorothy Branch, a former photo stylist for a magazine production company, FĂȘte & Vignette was born out of Dorothy’s love for creating stunning tablescapes, floral arrangements, and designing spaces that tell a story. Dorothy’s background in styling for editorial shoots, where she crafted beautiful settings for various themes and events, has equipped her wit...


The Burgess Collection
04/28/2026

Founded by Cathy Burgess, The Burgess Collection was born from a desire to redefine modern Luxury for women. Inspired 
By her love for Newport; a beautiful seaside city in Rhode Island. 
Born and raised in Rhode Island, Cathy studied fashion and retail in Boston. She started her career as a fashion sales rep for high end women's clothing. Cathy realized her potential to create her own brand and began designing and curating a line that she loved and felt was missing in the industry. Today, The Burgess Collection can be found in stores across the country making wo...


Finding Silver Pennies
04/21/2026

Danielle is a self trained watercolor artist and designer. She lives in Scituate, MA on Boston’s South Shore with her husband, two sons, and rescue dog. She found her creativity when starting her blog, Finding Silver Pennies, which has grown into a lifestyle brand and shop. Her work is inspired by the nature in her coastal town. Her work has been featured on WCVB’s Made in Mass and in What Women Create, South Shore Home Life, and Style, Boston Globe Magazine and more.  It’s her goal to help everyone find their inner creativity. Use code PreppyPodcast for 10...


Kelly Hughes Designs
04/14/2026

Kelly Hughes Designs is a stationery and gift company with a mission to spark happiness through our whimsical and delightful designs! All of our artwork is hand-illustrated by Kelly. She pays attention to the smallest details in products, with a focus on delivering high quality merchandise that brings joy to everyday life. Shop at https://kellyhughes.com/ 

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Kahora Palm Beach
04/07/2026

KAHORA has a distinct style that combines sophistication and femininity with a fun aesthetic. In 2021, KAHORA began with one silhouette-The La Guerite- and has naturally grown into a capsule collection of timeless dresses.

KAHORA inspires all women to embrace their individuality with confidence. Their artisans pay meticulous attention to the finer aspects of construction, ensuring that every piece is crafted with care. They only cut a small number of garments for each style intentionally, as we strive to keep our waste to a minimum.  Shop at https://kahorapalmbeach.com/ and use code preppypodcast20 for 20% off 

Su...


Shore Bags
03/31/2026

Made from sustainable raw materials in our family factory, ShoreBags's mission is to help reduce the amount of single-use plastic in the environment and empower local communities. We believe in ethical and fair manufacturing practices, transparent supply chains and creating bags that reflect the best in functionality and eco-fashion. Shop at https://shorebags.com/ and use code "FRIENDS30" for 30% off. 

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Flaire Lighting
03/24/2026

Flaire Lighting is a luxury brand redefining the world of portable, battery operated lighting. The story began with our founders, husband and wife team Andrew and Claire, who saw an opportunity while searching for a battery-powered lamp for their charming 1920s home, which had limited outlets. Frustrated by the lack of unique, functional options, Claire immediately began sketching ideas for a new design. Her vision was simple: add a little FLAIR to every space, while creating the most durable and high quality lamp on the market at a price point one could justify for the quality. With experience as...


Timeless Grace
03/17/2026

Timeless Grace Lifestyle Wear is a woman-owned small business based in St. Louis, Missouri, dedicated to helping women thrive in the many dimensions of modern life. We create luxurious yet functional garments that offer full coverage, comfort, and confidence—designed to support today’s woman in every role she embraces. Use code preppy20 for 20% off at https://timelessgracewear.com/

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Dana Small
03/10/2026

Dana Small is a South Florida based interior designer and the founder of Dana Small Designs, a full service firm specializing in residential projects of all sizes, from a single room refresh to full renovations and new builds.

Known for her thoughtful approach to space and style, Dana creates interiors that blend timeless tradition in with coastal charm. Her work feels elevated yet approachable, layered with color, texture, and personality. She often incorporates antique rattan, wicker, and bold hues to infuse warmth and character into every room.

With projects across the country and the Caribbean...


The Cookie Countess, Royal Mahjong Society and Crown & Coastal
03/03/2026

For over 13 years, Hilary Ramos built a company called The Cookie Countess into one of the most trusted and beloved brands in baking and the cookie-decorating world. Yup — it’s a thing. 😉 It’s a world where creativity, community, and craftsmanship come together.

After years of designing products that inspire joyful baking, she found herself falling in love with another kind of artistry: mahjong.

And in the same way The Cookie Countess began — as a hobby (or, some might say, an obsession) — mahjong quickly became my new creative outlet. She was captivated by the history of the game...


Up Down Sports
02/24/2026

Tennis is much more than a sport to this dedicated and engaged mother of four who lives in New York City. Her Friday tennis group, made up of close friends she’s known for over ten years, provided the spark and encouragement to create Up Down Sport. Week after week, they would show up with their tennis rackets in hand while juggling the day’s essentials. No one could find a bag they loved that could house their racket and all of the other things their active lives required. With an eye for design and detail, coupled with her ever...


Cowtown Clay
02/17/2026

Cowtown Clay  helps preserve your memories by creating professional impressions of your children’s hands and feet that will last a lifetime. They know too well that children grow up way too fast, and we find ourselves wanting to bottle up every stage- from newborn to preschool and beyond. Their own littles are the inspiration behind their craft- and while they can't slow the clock, they have found this wonderful way to remember their innocence for years to come. No two impressions are the exact same- every one is as unique and special as your child (or pet...


Timo & Violet
02/10/2026

Timo & Violet is devoted to creating timeless, enchanting products that honor nature, spark wonder, and are inspired by the world around us—proving that softness, beautiful prints, and sustainability can live beautifully together.

Every order plants a tree, laying down roots for tomorrow.

Learn more at https://timoandviolet.com 

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Tipsy Threads
02/03/2026

My name is Austin Gleason, but most people know me as AG (that’s a story for another time). I’m the owner and designer of Tipsy Threads, a brand born from creativity, change, and a leap of faith.

I graduated from The University of Alabama in 2020, and like many graduates at the time, my path was anything but traditional. I went from waiting tables in Tuscaloosa to selling clothing in Athens, Georgia from August 2020 to May 2022. Eventually, I moved to Fairhope, Alabama to help open that company’s fourth store—where I unexpectedly fell in love with fas...


Jennifer Scott
01/27/2026

Jennifer L. Scott is the New York Times bestselling author of Lessons from Madame Chic, At Home with Madame Chic and Polish Your Poise with Madame Chic, Mademoiselle Chic, and Connoisseur Kids. She is also the creator of the YouTube channel, The Daily Connoisseur, where she explores the fine art of living. Jennifer has been featured on CNN, BBC, CBS News, and in The New York Times, The Wall Street Journal, The Epoch Times, Vanity Fair, USA Today, Newsweek, and The Daily Mail. She and her family live in Southern California and the English countryside...