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2023 Preppy Style Photoshoot: 10 Outfits | 20 Captivating Photo Ideas

CEO Tinh Phung
The preppy fashion trend is making a glorious comeback in 2023, blending classic aesthetics with a modern twist. This ultimate guide offers valuable tips and innovative ideas to help you create unforgettable preppy-style photoshoots. Preppy...

The preppy fashion trend is making a glorious comeback in 2023, blending classic aesthetics with a modern twist. This ultimate guide offers valuable tips and innovative ideas to help you create unforgettable preppy-style photoshoots.

Preppy Style Evolution

1. How It All Began

The preppy style originated from the traditional clothing worn by students in elite preparatory schools and Ivy League universities in the United States during the early 20th century. It quickly gained popularity, becoming synonymous with social status, academic institutions, and a refined and sophisticated appearance.

2. The Fabulous 50s Preppy Style

In the 1950s, the preppy look embraced pastel colors, full skirts with appliques like poodle skirts, and neatly pleated skirts. Saddle shoes paired with ankle socks were a popular choice for footwear. Here's a glimpse of the iconic 50s preppy style:

The 50s Preppy Style

Photo by Les Anderson on unsplash

3. The Trendy 80s Preppy Style

The 80s witnessed the rise of preppy fashion after "The Official Preppy Handbook" was released, encouraging the adoption of khakis, plaid blazers, and tied sweaters. It was a decade marked by confident and polished looks.

4. The Trendy 90s Preppy Style

The 90s preppy style embraced lower-rise pants and boot-cut styles, incorporating plaid patterns and tying shirts around the waist. It exuded a relaxed and vibrant vibe, reflecting the youthful spirit of the decade.

5. The Millennium Preppy Style

In the early 2000s, preppy fashion took a bold turn by incorporating vibrant colors and playful elements. However, the rise of athleisure in 2015 led to a shift towards comfortable joggers and leggings, overshadowing the traditional preppy style.

The 2000s Preppy Style

Photo by ESB Professional on shutterstock

6. The Revival of Preppy Fashion

Today, the preppy style is making a strong comeback, as evidenced by its prominent presence in Fashion Weeks. Esteemed designers like Chloé, Michael Kors, Burberry, Versace, and Dior have showcased various preppy elements, reigniting the trend's popularity.

Guides for Preppy Photoshoots in 2023

Preppy Outfits (Men/Women)

If you're looking to create a classic preppy outfit, consider timeless knitwear. A cozy and elegant knit sweater or cardigan never goes out of style. Combine it with other preppy staples to create a sophisticated ensemble.

Timeless Knitwear

Photo by Mentatdgt on shutterstock

Another essential item for a refined and polished look is loafers. For men, wearing sophisticated loafers adds a touch of class to their ensemble.


Photo by David Karp on unsplash

Preppy Style Staples: Adding Character to Your Outfit

To showcase the timeless charm of the preppy style, incorporate plaid and polka-dot patterns into your outfits. These playful yet sophisticated patterns add a touch of personality to your look.

Plaid & Polka-Dot Patterns

Photo by Norbert Braun on unsplash

Touches of shearling can also elevate your preppy outfits. Luxurious shearling details, such as collar trims or lining, add a touch of luxury and warmth to your style.

Touches of Shearling

Photo by Anna Zhuk on shutterstock

For a feminine and sophisticated look, consider incorporating pleated skirts into your preppy ensemble. Pleated skirts add an elegant and timeless touch to your overall outfit.

Pleated Skirts

Photo by Sean Kong on unsplash

Button-down shirts are a classic staple of the preppy style. They provide a polished and tailored appearance, perfect for any occasion.


Photo by Rui Silvestre on unsplash

To add a vintage touch to your preppy outfit, consider incorporating Mary Jane shoes. These retro-inspired shoes bring a sense of nostalgia and elegance to your overall look.

Mary Janes

Photo by Kelly Sikkema on unsplash

To infuse a sporty and collegiate aesthetic into your preppy outfits, opt for varsity-inspired sweaters and jackets. These pieces represent a timeless and energetic style.

Varsity Sweaters & Jackets

Photo by Te9l on shutterstock

For a polished and refined preppy look, reach for khakis or chino pants. These versatile bottoms provide a tailored and sophisticated option for any occasion.

Khakis & Trousers

Photo by Pixs4u on shutterstock

The sweater vest is a timeless preppy garment that adds a touch of sophistication to any outfit. It's the perfect layering piece to complete your preppy look.

The Sweater Vest

Photo by Ben Iwara on unsplash

20 Captivating Preppy Photoshoot Ideas

1. Preppy Graduation Photoshoot

Symbolize the completion of an educational journey by having your model hold a suitcase in school uniforms. Capture the emotions of accomplishment and excitement in stunning photographs.

Preppy Graduation Photoshoot

Photo by Romsavka on shutterstock

2. Reimagined Iconic Movie

Dress your model as your favorite movie/TV character, recreating their iconic outfit, hairstyle/makeup, and unleashing your creative imagination.

Reimagined Iconic Movie

Photo by Volodymyr Shtun on shutterstock

3. Unforgettable Group Portraits

Gather your friends, dress in casual preppy outfits, strike a pose as a group, and capture the perfect shot that encapsulates the fun and camaraderie forever.

Unforgettable Group Portraits

Photo by Priscilla Du Preez on unsplash

4. Charming Schoolgirl Style

Dress your model in a woolen vest sweater, loafers, and neat white ankle socks for a timeless and playful look.

Charming Schoolgirl Style

Photo by Eye for Ebony on unsplash

5. Tennis Fever

Immerse yourself in the golden era of Ivy League sports excellence by dressing your model in a throwback preppy tennis outfit. Complete the look with tennis accessories and classic tennis jewelry.

Tennis Fever

Photo by Christian Tenguan on unsplash

6. Mystery Girl

Create a fashion-mystery ambiance by dressing your model in a stylish preppy outfit. Have them artfully hide their face with a phone or handbag, capturing an air of intrigue.

Mystery Girl

Photo by Sincerely-media on unsplash

7. Beach Dresses

Embrace the vibrant spirit of the 2000s with colorful beach preppy outfits. Capture spontaneous candid photos that embody the carefree essence of coastal living and the effortless style of beach dresses.

Beach Dresses

Photo by Iam Os on unsplash

8. Stylish Outdoor Soiree

Immerse yourself in a delightful preppy picnic experience. Dress attendees in traditional preppy clothes and hats, capturing the elegance of outdoor gatherings.

Stylish Outdoor Soiree

Photo by David Pereiras on shutterstock

9. Preppy Golfing Style

Dress your models in golfing attire, have them handle props like golf clubs, and set the scene at a picturesque golf course. Capture the grace and style of a preppy golfer.

Preppy Golfing Style

Photo by Cristhian Rojas on unsplash

10. A Classy Approach to Study Time

Dress in khaki trousers and a blazer, add books as props, and capture a sophisticated academic vibe. Channel the timeless elegance of preppy scholars.

A Classy Approach to Study Time

Photo by Helena Lopes on unsplash

These are just a few of the captivating preppy photoshoot ideas to inspire your creativity. Explore different themes and settings to bring your vision to life.


Preppy fashion remains an enduring source of inspiration, offering a fusion of timeless elegance and modern flair. Whether you embrace the classic elements or add your personal twist, the preppy style continues to captivate with its sophistication, charm, and enduring appeal. It's time to embrace this fashion trend and create stunning photos that reflect your unique style.

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