11 Best Southern Preppy Brands You’ll Love to Wear

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Genuine Southern Preppy brands able to epitomize the style’s blend of classic elegance and relaxed charm are just a few and kept secret by Preppy connoisseurs.

In this article, I’ll introduce you to the 11 best Southern Preppy names, a curated selection from over 100 high-profile brands specializing in Preppy clothing, footwear, and accessories.

With heritage and years of expertise, these brands are at the top of the list with silhouettes that blend Southern aesthetics with modern looks for a chic vibe you won’t find anywhere else.

1. Lilly Pulitzer

Best for Coastal-Themed Summer Preppy Apparel

Lilly Pulitzer Southern Preppy

Founded in Palm Beach, Florida, in the late 1950s, Lilly Pulitzer is a Preppy fashion label synonymous with the coastal allure of the South.

The brand’s unmistakable prints depict seaside landscapes, tropical florals, and marine life in colors inspired by sun-soaked afternoons and balmy evenings.

Whether it’s dresses, tops, or accessories, Lilly Pulitzer’s creations capture the essence of Southern leisure and the relaxed elegance of beachside living.

Lilly Pulitzer Mila Stretch Shift Dress Lilly Pulitzer Luxletic Brickell Dress

2. Vineyard Vines

Best for Button-downs, Shep Shirts, and Club Shorts

Vineyard Vines Southern Preppy

Launched in 1998 on Martha’s Vineyard, Vineyard Vines specializes in casual wear for Southern leisure activities such as boating, horse riding, and golfing.

With themes inspired by beach, ocean, seashells, fish, and boats, the brand’s printed button-down shirts are essential to Southern coastline ensembles.

The brand’s Shep shirts, made of breathable cotton and club shorts in regional patterns, are excellent options for an authentic Southern Preppy look.

Vineyard Vines Heritage Polo Vineyard Vines Large Heritage Classic Tote

3. Jack Rogers

Best for Whipstitched Sandals and Woven Leather Footwear

Jack Rogers Southern Preppy

Jack Rogers gained popularity with the Preppy fashionistas thanks to Jackie Kennedy after she was spotted wearing the brand’s now-iconic whipstitched sandals.

Since then, JR’s sandals, recognizable by their distinctive rondelles and whipstitching, have become wardrobe staples for Southern Preppy enthusiasts.

Perfect for warm Southern climates, Jack Rogers’ woven leather footwear is a must-have for summer gatherings and coastal getaways.

Jack Rogers is best known for its iconic Whipstitched sandals, woven leather, and suede footwear.

Jack Roger Jacks Flat Sandal Jack Roger Hunley Tassel Loafer

4. J Crew

Best for Lightweight Chinos, Shirts, and Comfortable Ballet Flats

JCrew Southern Preppy
Image courtesy: @spiritedpursuit

Since 1983, J Crew has skillfully blended tradition with modernity into garments suitable for the warm Southern climate.

The brand’s lightweight chinos, perfect for balmy days, breathable cotton shirts in humid environments, and cushioned ballet flats are loved staples in the Southern Preppy style.

With a keen eye on quality materials and meticulous design, J Crew outfits and footwear are enduring, stylish, and comfortable, encapsulating the modern Southern Preppy vibe.

JCrew Ruffle-collar long-sleeve shirt in striped vintage rib JCrew Sailor heritage chino pant

5. Brooks Brothers

Best for Tailored Suits and Dress Shirts

Brooks Brothers Southern Preppy

Established in 1818, Brooks Brothers is a pioneer American clothing retailer known for introducing the ready-to-wear suit to the U.S. market.

With roots in New York City’s cosmopolite aesthetic, the brand carved a niche among the nation’s elite thanks to bespoke tailoring suits, dress shirts, and classic Preppy ties.

Over the decades, Brooks Brothers has upheld its commitment to exceptional craftsmanship and timeless designs, becoming a staple for Southern Preppy fashionistas seeking to depict sophistication.

Brooks Brothers Linen Pleated Wide Leg Pants Brooks Brothers Linen Short Sleeve Polo

6. Sperry

Best for Boat Shoes and Preppy Essentials

Sperry Southern Preppy

Since its inception in 1935, Sperry has been a hallmark in Southern Preppy fashion and synonymous with its iconic boat shoe, also known as the “Top-Sider.”

Initially designed to provide better traction on wet decks, the world’s first boat shoe became trendy and gained tremendous popularity beyond boating circles.

With a solid nautical heritage, quality craftsmanship, and iconic designs depicting maritime life, Sperry is an essential clothing brand for the Southern Preppy style.

Sperry Boat Shoes Sperry Leather Loafer Boat Shoes

7. Tommy Hilfiger

Best for Tops and Jackets in Iconic Stripe Patterns

Tommy Hilfiger Southern Preppy

Established in 1985, Tommy Hilfiger captures the essence of American heritage, weaving contemporary fashion trends into traditional Preppy aesthetics.

Tommy Hilfiger’s breathable cotton polo shirts in red, white, and blue stripe patterns, symbolic of the brand’s identity, are ideal for the warm, humid climate.

Complete your look with white chinos and brown leather boat shoes in a perfect blend of tradition and contemporary flair that embodies Southern Preppy’s visual sophistication.


8. L.L.Bean

Best for Canvas Tote Bags, Lightweight Chinos, and Slip-On Loafers

L.L.Bean Southern Preppy

Launched in 1912, L.L. Bean gained early fame thanks to its outdoor gear that earned a steady place in Southern Preppy style.

The label is famous for durable canvas tote bags and lightweight chinos – Southern outing staples from the beach to a picnic in the park.

Combine them with slip-on loafers for a breathable, comfortable ensemble ideal for Southern heat.

L.L.Bean Women's Wrinkle-Free Bayside Shorts, Ultra High-Rise Hidden Comfort Waist 9" L.L.Bean Women's Soft Stretch Supima Tee, Crewneck Short-Sleeve Striped

9. Tory Burch

Best for Ballet Flats, Handbags, and Feminine Sundresses

Tory Burch Southern Preppy

Established in 2004, Tory Burch became synonymous with luxurious American Preppy style infused with a bohemian twist.

The brand’s ballet flats adorned with a medallion logo confer any Preppy outfit with a touch of upscale elegance.

However, the best Tory Burch garment that fits the Southern Preppy style is the brand’s tunic in colors reminiscent of sunny seaside vacations.

Tory Burch is best for embellished ballet flats, patterned tunics, and leather tote bags.


10. Kate Spade

Best for Pearl Necklaces, Handbags with Bow Accents, and Dresses

Kate Spade Southern Preppy

Founded in 1993, Kate Spade New York excels in detailed Preppy accessories and outstanding garments.

Spade’s knee-length dresses, from breathable cotton and seersucker, are perfect for the Southern hot and humid climate.

Accessorize with pearl necklaces, charm bracelets, and leather handbags adorned with bow accents or scalloped edges for a touch of traditional sophistication to your Southern Preppy look.

Kate Spade Leandra Loafers Kate Spade Awning Stripe Tie-waist Dress

11. Draper James

Best for Midi Dresses, Seersucker Pants, and Gingham Accessories

Draper James Southern Preppy

Founded by actress Reese Witherspoon in 2015, Draper James clothing and accessories exemplify Southern charm and hospitality.

The brand’s floral midi dresses are quintessentially Southern and perfect for garden parties or Sunday church services.

The brand is also excellent for gingham pattern handbags, scarves, and seersucker pants made of lightweight, breathable fabric suitable for Southern heat.

Draper James Fit & Flare Dress in Gingham Draper James Woven Pull On Shorts in Lily Floral

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Keep up with the latest in fashion, beauty and style!

Key Takeaways

From the enduring legacy of Brooks Brothers’ meticulously tailored suits to the Southern charm of Draper James’ floral midi dresses, this guide has the best Southern Preppy brands.

It is essential to understand that, compared to Ivy League and Northern Preppy, the Southern Preppy style is lighter and more colorful.

The style has a cheerful and relaxed look that blends the traditional sophistication of classic Preppy with the comfort required for the Southern climate.

After years of managing hundreds of fashion brands from London's office of a global retailer, Mandy has ventured into freelancing. Connected with several fashion retailers and media platforms in the US, Australia, and the UK, Mandy uses her expertise to consult for emerging fashion brands create top-notch content as an editorial strategist for several online publications.

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