Journaling is a wonderful way to express yourself, capture memories, and reflect on your preppy lifestyle.
Whether you’re a seasoned journal writer or just starting out, sometimes it’s hard to know what to write about.
That’s where this ultimate guide comes in!
We’ll cover:
- Fun and creative writing prompts to inspire you
- Tips for documenting your preppy fashion and experiences
- Ideas for reflecting on your personal growth and aspirations
- Suggestions for tracking your friendships and social life
By the end, you’ll have plenty of preppy journaling ideas to fill up those crisp, monogrammed pages.
So grab your favorite pen and let’s dive in!
1. Describe your dream preppy outfit
One of the most enjoyable things to journal about is fashion, especially if you love the preppy aesthetic. Spend some time envisioning your ideal preppy ensemble from head to toe. Would it be a classic combo like a navy blazer, crisp white button-down, khakis, and penny loafers? Or maybe a bright Lilly Pulitzer sundress with Jack Rogers sandals for a summer soirée?
Get detailed in your description, noting the brands, colors, patterns, and accessories. You could even sketch it out if you’re feeling artsy. This is a great way to get inspiration for future outfits or refine your signature preppy style. Don’t forget to include how the outfit makes you feel – confident, polished, ready for anything!
2. Recount a memorable experience at a preppy event
Preppies love a good social gathering, from tailgates to tennis tournaments to garden parties. Think back on a recent event you attended that had a particularly preppy vibe. Maybe it was a charity gala where everyone was decked out in seersucker and sundresses. Or a sailing regatta where you cheered on your friends from the host yacht.
Jot down the details that made the event special. What did you wear? Who was there? Describe the setting, the food and drinks, the music, and the conversations. Reflect on how you felt being part of that preppy community. Was it exhilarating, comforting, inspiring? Capturing these memories in your journal allows you to relive the fun whenever you read back on it.
3. List your top 5 preppy style icons
Every preppy has a few fashion idols who perfectly embody the aesthetic. They could be classic style icons like Jackie Kennedy, modern preppy muses like Olivia Palermo, or even fictional characters (hello, Blair Waldorf). Make a list of your top five, and then elaborate on what you admire about each one’s style.
You can go into detail about their signature pieces, color palettes, or styling tricks and how you might incorporate those into your look. Over time, your style icons might change, so it’s fun to look back and see the evolution. Be sure to include some images if you have them – a picture is worth a thousand words, especially when it comes to fashion!
4. Set some preppy goals for the season
A new season is the perfect time to set some fresh preppy goals. Think about the preppy activities and experiences you want to have in the coming months. Maybe you want to attend your first polo match, host an epic Nantucket-themed dinner party, or finally splurge on those Stubbs & Wootton slippers you’ve been eyeing.
Write out your top goals and the steps you’ll take to achieve them. Be specific and motivating in your language. Instead of writing “Go shopping,” put “Update my wardrobe with classic preppy staples like cable knits and plaid skirts.” And don’t just focus on fashion – consider goals around preppy travel destinations, sports to try, books to read, or skills to learn. Aim high!
5. Reflect on a meaningful conversation with a preppy friend
Preppies value community and connections, and some of the best moments happen when connecting with friends. Reflect on a recent heartfelt conversation you had with a fellow preppy, whether it was seeking advice from an older sorority sister or catching up with your oldest friend from boarding school over G&Ts.
Write about what you discussed and how it made you feel. Did your friend share some words of wisdom or a hilarious story? Did you gain a new perspective or feel reassured about something? Perhaps it sparked an idea for your personal growth. Getting these thoughts and feelings down on paper can be cathartic and help you process them. And when you look back, you’ll smile remembering that special bond.
6. Plan your dream preppy vacation
Many preppies have a passion for travel, especially to classic East Coast destinations. Let your mind wander to your ideal getaway, and record all the details. Would it be a cozy fall weekend in Nantucket complete with sailing, seafood, and strolls on the beach? Or maybe a summer road trip along the coast, popping into preppy towns and staying in charming B&Bs?
Get specific with your itinerary, imagining the activities you’d do, the restaurants you’d try, and the outfits you’d pack. Describe the accommodations, whether it’s a historic inn or a sprawling beach house with friends. By the end, you should feel transported and motivated to make it happen. Even if you can’t swing the whole trip now, pick one or two elements to incorporate into your real life, like hosting a clambake-themed dinner party or going for sunset sails on a local lake.
7. Write about a time you embodied preppy values
The preppy subculture isn’t just about clothes – it’s also a set of values and a way of carrying yourself. Reflect on a recent situation where you feel like you embodied the best of preppy ideals. Maybe you volunteered your time for a good cause and rallied friends to help. Or you demonstrated good sportsmanship in a tough tennis match. Perhaps you wrote heartfelt thank you notes after attending a gala.
Recount how you handled yourself and how it made you feel to live up to those standards. Dig into why those values resonate with you. This journaling helps shape your identity and moral compass. We aren’t perfect, but reflecting on the times we get it right can help us choose that path forward again and again. Give yourself a little pat on the back.
8. Muse on your preppy role models
In addition to preppy-style icons, many of us have real-life preppy role models. These are the people who inspire us with their grace, integrity, success, and joie de vivre. Maybe it’s your poised and philanthropic sorority mentor or your friend’s dad who is a world-class sailor and brilliant executive. Perhaps it’s a professor who exemplifies preppy intellectualism and wit.
Identify a few of your role models and journal about what you admire in them. What qualities do they have that you’d like to emulate? What can you learn from their path? You could even write about how you met them and why they’ve been impactful in your life. Then, consider ways you might strengthen that relationship or follow their example. A little hero worship never hurts!
9. Brainstorm preppy party themes
Preppies love to entertain, and coming up with creative party themes is half the fun. Use your journal to brainstorm concepts for your next soirée. A garden party with croquet and G&Ts, perhaps? Or what about an Ivy League rivalry tailgate with each guest representing their school?
Get detailed with your ideas from the signature cocktail to the dress code. Sketch some decor ideas or make a sample menu. Having these blueprints in your journal will make party planning a breeze. Your friends will be wowed by your hosting prowess! Just don’t forget to journal about the actual event later to record the memories.
10. Dream up your ideal preppy home decor
Your preppy taste shouldn’t stop at your closet – it should extend to your space too! Whether you’re decorating a dorm room, first apartment or forever home, it’s fun to envision your ultimate preppy sanctuary. Create a mood board in your journal with images and descriptions of your favorite preppy decor elements.
Scour magazines and design blogs for inspiration and jot down what catches your eye. A blue and white color palette? Sailing motifs? Chinoiserie wallpaper? Seersucker bedding? The options are endless. Get a clear vision and then make a plan to gradually acquire key pieces. With every addition, your home will feel more like a reflection of you. And you’ll always have these early ideas to look back on fondly!
11. List your preppy essentials
Every preppy gal has her go-to essentials that make her feel put together and in her element. Make a list of your ultimate preppy must-haves, from fashion staples to beauty products to chic stationery. Think: a perfect fitting navy blazer, monogrammed Lo & Sons tote, Bobbi Brown makeup, Dempsey & Carroll notecards.
Then expand on why each item cuts. How does it make your life easier or more stylish? What’s the story behind it? Creating this list not only helps you identify the foundation of your preppy lifestyle but also makes packing and shopping a breeze. It becomes a checklist to keep your preppy game strong! As you test out new products, update the list with your honest reviews.
12. Jot down your favorite preppy quotes & phrases
Preppies have a way with words, from clever quips to cheeky phrases. Start keeping a running list of your favorite preppy expressions to pepper into conversation and writing. You’ll hear them everywhere from the tennis court to the cocktail party. “She’s a real Muffy!” “He’s such a bro.” “It’s 5 o’clock somewhere!”
Don’t stop at mainstream phrases – include family idioms, inside jokes with friends, or funny things your professors say. Over time you’ll have an incredible collection of witticisms that make you smile and remind you of your people. You can also include famous preppy quotes from movies, books, or real lifestyle icons. Having these words of wisdom at your fingertips will keep you in a preppy frame of mind!
13. Review a preppy book
Literature is a big part of preppy culture, and nothing beats cozying up with a classic. After your next read, take the time to journal a thoughtful review. Maybe it’s a coming-of-age story set at a boarding school or a historical romance in a seaside town. How did the setting and characters embody the preppy ethos? What themes resonated with you?
Don’t just summarize the plot – dig into your takeaways. Did it change your perspective or inspire you in some way? Would you recommend it to friends? Putting your analysis into words helps you engage more deeply with the book. You could even start a virtual book club and share your reviews. Becoming a more critical reader will take your prep school smarts to the next level!
14. Reflect on a preppy rite of passage
Preppy culture has its share of iconic experiences that act as rites of passage. From your first sailing lesson at age 7 to your debutante ball to your college graduation, these milestone moments define your coming of age. Pick one that you’ve recently gone through and reflect on its significance.
Set the scene in detail from what you wore to who was there. What emotions did you feel – nerves, pride, excitement? How did it test you or change you? What did it teach you about yourself? Recording these major life events builds your legacy. And it’s always enlightening to see how your perspective on it shifts over time. You might even want to tuck a memento from the experience into the pages!
15. Create preppy playlists
Music can be such a mood booster and memory maker. Have some fun in your journal by creating the ultimate preppy playlists for any occasion! Make one for a road trip to the Cape filled with oldies and yacht rock. Another for getting hyped up before a regatta with upbeat indie tracks. And of course, a dinner party mix that’s heavy on the Sinatra.
Not only will you end up with amazing playlists to use in IRL, but you’ll also get to express your personality and savor happy preppy memories associated with each song. Challenge yourself to discover new artists that fit your aesthetic. And ask your friends for their suggestions! A shared playlist can bond you over music and become a time capsule of a certain era.
16. Plan a preppy DIY project
Preppies are known for being industrious and resourceful. If you’re the crafty type, use your journal to plan out your next DIY project with a preppy twist. Maybe it’s cross-stitching Nantucket-style cocktail napkins, building wooden sailboat bookends, or sewing ribbon belts in every color.
Sketch out your design, make a supplies list, and outline the steps. This prep work ensures a smooth crafting session and a polished final product. Get creative with ways to personalize the project with your monogram or favorite preppy motifs. As you work, journal about the process – the challenges, the aha moments, the sense of accomplishment. Flex that artsy prep school kid muscle!
17. Map out your preppy family tree
Legacy is a huge part of preppy culture, so family history is a natural thing to explore in your journal. Start by mapping out a family tree, going back a few generations. Include names, birth/death dates, hometowns, schools, and careers. But also focus on the more colorful details and anecdotes that get passed down.
Maybe your great-grandfather started a tennis club that’s still around today. Or your grandma was the first woman in the family to get an Ivy League degree. Putting these stories to paper preserves them for posterity. Share the project with your relatives and see what they can add. You might decide to dig through photo albums and scrapbooks to add visuals. It’s a meaningful way to connect with your roots and your kin.
18. Paste in preppy inspiration
Journals aren’t limited to your writing – use yours to collect visual inspiration too. Whenever you come across a preppy image that speaks to you, paste it in and jot down a reflection. It could be a magazine ad with an outfit you love, a resort postcard, a ribbon from a party favor, or a paint chip in your fave shade of pink.
Suddenly your journal becomes a mood board that both informs your aesthetic and sparks your creativity. Add inspiring quotes, cheeky puns, posh shopping bags. Let it be a collage of your interests and aspirations. Flipping through this preppy scrapbook will make you smile, transport you, and maybe even shape your next chapters. Don’t be too precious – let it evolve along with you!
19. Write a letter to your younger preppy self
Hindsight is 20/20, as they say. Have you learned some key lessons in your preppy journey so far? Found your confidence or your true crew? Achieved a big goal or made a bold change? Journal it out in the form of a letter to your younger self.
Think back to a specific moment when you could’ve used that perspective or pep talk. Set the scene, then share what you would say now with love and wisdom. The advice can be deep and heartfelt or practical and lighthearted. The point is to recognize how far you’ve come and the insights you’ve gained. It’s a chance to nurture yourself at different stages. You could even make it a ritual, writing a new letter every birthday.
20. Free write about your preppy dreams
Not every journal entry needs a purpose or prompt. One of the most liberating things you can do is simply let yourself free to write about your wildest preppy dreams – no filter, no judgment. Set a timer for 10 minutes and just let it flow in a stream of consciousness.
You might find yourself gushing about your fantasy home on Martha’s Vineyard or an imagined flirtation with a handsome stranger at the Derby. The more you do this practice, the more you’ll tap into your innermost desires and ideas. It’s like your preppy subconscious taking the wheel. Over time, patterns emerge. Passions crystalize. True wishes float to the surface. And voilà, you have a treasure map to your most fulfilling future. Sure, not every random thought will be a winner, but there’ll be some gems in there if you let yourself play. It’s your journal, your imagination, your rules!
Conclusion
By now, your preppy journal should be bursting with personality, memories, and inspiration.
Whether you tackled every prompt or just the ones that called to you, you’ve created a portal into your perspective and experiences.
Whenever you need a dose of nostalgia, motivation, or self-reflection, you’ll have this trusty companion to revisit.
Remember, your preppy journal is a constant work in progress, just like you.
There’s no wrong way to fill its pages.
Let it be a place for your most authentic self to shine through – seersucker and all.
Happy writing!