Size-Inclusive Preppy Summer Looks to Feel Confident & Stylish

by Yvette in Comment — Updated June 7, 2024

The preppy look has long been a classic and timeless style choice, especially during the summer when the sun is shining and the days are long.

Originating from Ivy League colleges, this fashion trend is known for its sophisticated yet casual vibe, making it an excellent choice for summer. 

With its clean lines, bright colors, and nautical influences, preppy fashion exudes a sense of elegance that is perfect for any occasion. A look into the history of vintage preppy style reveals timeless trends.

However, the fashion industry has often overlooked the importance of size inclusivity, leaving many women feeling left out of the preppy fashion world. But fear not, as more size-inclusive options allow women of all shapes and sizes to rock the preppy look with confidence and style.

This article’ll explore the key elements of classic preppy style and highlight various size-inclusive options to help you put together chic, summer-ready outfits.

From button-down shirts and polo tops to shorts, skirts, and dresses, you’ll find an abundance of high-quality, thoughtfully designed preppy pieces to suit your personal taste.

We’ll also discover top brands that cater to a wide range of sizes how to incorporate bright colors and fun prints, and provide tips for different occasions.

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Key Takeaway

  • Preppy fashion is characterized by clean lines, bright colors, and nautical influences, making it a sophisticated yet casual style perfect for summer.
  • Key elements of preppy style include button-down shirts, polo tops, solid-colored shorts, linen pants, and classic footwear like boat shoes and espadrilles, all of which provide a polished and versatile look.
  • Accessories such as sunglasses, baseball hats, oversized pearl earrings, and tote bags play a crucial role in completing the preppy outfit, adding both functionality and a touch of elegance.
  • The fashion industry is increasingly embracing size inclusivity, with brands like Ralph Lauren and Vineyard Vines offering preppy styles in a wide range of sizes, allowing women of all body types to confidently wear preppy fashion.

Key Elements of Classic Preppy Style

The classic preppy style is defined by its clean lines, timeless pieces, and polished appearance. Here are some key elements that form the foundation of preppy fashion, ensuring you look effortlessly stylish and put together.

Button-down Shirts and Polo Shirts

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Button-down shirts and polo shirts are quintessential pieces in any preppy wardrobe. For a retro twist, consider a 70s floral sleeveless shirt, which adds a playful touch.

These versatile shirt styles can be dressed up or down, making them perfect for various summer activities. Brands like Ralph Lauren and Vineyard Vines offer a wide range of styles and fits, ensuring you find the perfect piece.

Solid-Colored Shorts and Linen Pants

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Solid-colored shorts and linen pants are staples of preppy fashion. They provide a clean, polished look while being comfortable enough for hot summer days. Pairing these with a crisp white shirt or a brightly colored top can create a balanced and stylish outfit.

Boat Shoes and Preppy Summer Shoes

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Classic footwear choices such as boat shoes, loafers, and espadrilles are integral to achieving a preppy summer look. They are stylish, comfortable, and perfect for various summer activities.

Boat shoes, in particular, are synonymous with preppy style. They are known for their durability and slip-resistant soles, making them ideal for both seaside and everyday wear.

Loafers and espadrilles add a touch of elegance and are versatile enough for various summer activities. Other great options include preppy summer shoes like Jack Rogers sandals, which add elegance to any outfit.

Sunglasses, Baseball Hats, and Oversized Pearl Earrings

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Accessories play a crucial role in completing the preppy look. A pair of sunglasses and a baseball hat can add a casual yet stylish touch to your outfit. Sunglasses also protect from the sun.

For a more classic touch, oversized pearl earrings are perfect for adding a bit of sophistication.

Incorporating Bright Colors and Fun Prints

Color is central to preppy style, especially in summer. Bright colors are a hallmark of preppy fashion, infusing your wardrobe with a cheerful, vibrant vibe perfect for the season.

Classic shades like navy, various blues, and crisp whites form the foundation of a preppy wardrobe, evoking the nautical vibes synonymous with summer yachting.

Lilly Pulitzer and the Iconic Preppy Color Palette

Lilly Pulitzer is renowned for her vibrant, eye-catching color palettes that have become iconic in preppy fashion.

These palettes often feature bright pinks, lush greens, and deep blues, providing a fresh and lively aesthetic perfect for summer apparel. Incorporating these colors can transform any outfit into a joyful and stylish statement piece.

Mixing and Matching Bright Colors and Fun Prints

Achieving a lively preppy look involves embracing a mix of bright colors and fun prints. Patterns like nautical stripes, gingham, and plaid are staples in preppy fashion.

Gingham, with its clean and bright appearance, is particularly suited for warm weather and can be found in everything from dresses to casual shorts. Pairing these patterns with solid colors can balance the look, making it vibrant yet harmonious.

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Size-Inclusive Brands and Retailers

Melly M. Designs

Melly M. Designs stands out in preppy-style clothing, offering garments that blend traditional aesthetics with modern flair. Their collections are known for their original designs and premium print selections, appealing to a broad audience.

High-quality materials ensure durability and comfort, while relaxed silhouettes cater to various body types, emphasizing the brand’s commitment to size inclusivity.

Ralph Lauren and Vineyard Vines

Ralph Lauren and Vineyard Vines are synonymous with classic preppy staples, offering a wide selection of apparel that appeals to modern women. Celebrated for their fashionable wear suitable for special events, these brands embody elegance and timeless style.

Both have made significant strides in embracing size inclusivity, ensuring their beloved styles are available in a more extensive range of sizes. This approach broadens their market and aligns with the growing demand for fashion that respects and celebrates diverse body types.

Styling Tips for Different Occasions

Casual Summer Outfits for Hot Summer Days

For those sweltering summer days, a preppy wardrobe can offer both style and comfort. Start with a classic polo shirt or a breezy, floral print dress that mirrors the free-spirited nature of bohemian style. Pair these with light-colored chinos or a vibrant pair of shorts to keep the look fresh and cool.

Accessorize minimally with a simple pair of sandals or boat shoes to complete the casual yet chic ensemble.

Dressing for Country Clubs and Golf Courses

For country clubs and golf courses, a collared shirt paired with crisp white shorts or a tennis skirt is a perfect choice. Add a pair of Jack Rogers sandals for the perfect finishing touch.

Preppy Outfits for Formal Occasions and Special Events

When dressing for more formal events, preppy fashion offers a timeless charm that is both elegant and appropriate.

Choose a structured blazer paired with a pleated skirt or a full-length preppy dress in a classic print. Enhance the outfit with high-quality accessories such as oversized pearl earrings or a sophisticated watch.

A stylish dress from Melly M. accessorized with oversized pearl earrings and a pair of Anna jeweled sandals, makes for a sophisticated ensemble.

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Adding a Little Bit of Sparkle with the Trend of Shimmery Sandals

Incorporating shimmery sandals into your preppy summer wardrobe can elevate even the simplest outfits.

These twinkling sandals work wonderfully with casual and formal wear, adding a glamorous touch without overpowering the look.

Pair them with everything from white jeans for a laid-back spring vibe to a sleek slip dress for evening affairs. Sparkly footwear’s versatility allows you to transition effortlessly from day to night while maintaining a chic and cohesive preppy style.

Accessorizing Your Preppy Look

The Perfect Finishing Touch: Jack Rogers Sandals

Jack Rogers sandals are renowned for their classic charm and versatility, making them an essential accessory for any preppy summer outfit. These sandals provide a polished look that complements a variety of ensembles, from casual shorts and polo shirts to more formal summer dresses.

Tote Bags for a Beachy Vacation

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Tote bags are not just practical; they are a style statement for beachy vacations and summer outings. Choose designs that feature bright colors and fun prints to embody the preppy vibe. These bags are spacious enough to carry all your essentials, like sunscreen, a good book, and a towel, while still being stylish.

A striped or nautically themed tote bag aligns perfectly with the preppy style, making it a must-have accessory for any seaside adventure.

Statement Pieces with Gorgeous Gemstones

Incorporating statement pieces such as jewelry with gorgeous gemstones can elevate your preppy look, adding a layer of sophistication and sparkle.

Pearls, often associated with preppy fashion, symbolize purity and elegance and work beautifully with both casual and formal preppy outfits.

Consider oversized pearl earrings or a pearl bauble necklace to add a classic touch, or choose bracelets and rings with colorful gemstones to inject a bit of fun and personality into your ensemble. These pieces not only enhance the outfit but also boost confidence with their eye-catching appeal.

Confidence-Boosting Accessories

Accessories can significantly boost your confidence. Whether it’s a pair of stylish sunglasses, a baseball hat, or an oversized pearl earring, these elements can enhance your overall look and make you feel great.


Size-inclusive preppy summer looks are the perfect way to feel confident and stylish this season. By incorporating key elements of classic preppy style and embracing bright colors and fun prints, you can create a look uniquely you. Shop at size-inclusive brands and retailers to ensure a perfect fit.

So, go ahead and experiment with your personal style. Remember that the beauty of modern preppy wear lies in its ability to make a much bigger impact when it is size-inclusive. Experiment with your look, and enjoy the confidence of dressing in a way that truly represents you.

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