There’s something irresistibly crisp—dare I say poetic—about summer prep. It’s structured but breezy, nostalgic with a wink. And lately, it’s having a vibrant little revival.
We’re not talking about stuffy blazers or elbow-patched professors. The new prep for casual summer outfits is more relaxed, more artistic. Think: tennis skirts with a twist, striped polos turned graphic tees, and a wardrobe made for docked sailboats, golden hour matches, and iced lattes.
At The Striped Palm, we live where preppy charm meets playful imagination. If you’ve ever dreamed of boating before brunch or collecting seashells in a crisp monogrammed cap, this one’s for you. Here’s how to style 5 casual-meets-polished summer outfits, each built around our buttery-soft graphic tees.
Table of Contents
5 Casual Summer Outfits With A Preppy Twist
1. The off-duty club member
What she’s wearing:
- White pleated skirt
- Striped Palm brunch tee, tucked just right
- Low-top tennis sneakers and crew socks
- Silk scarf + glossed lips

SHOP THIS LOOK ON LTK: https://liketk.it/5eAbZ
She’s sporty, but make it soft. Whether she just aced her doubles match or skipped to mimosas instead, she looks like summer prep personified—fresh, effortless, and just a little bit flirty. 🏸
📍 Perfect for: brunch al fresco, pickleball warmups, driving convertibles without a care.
2. The dockside daydreamer
What she’s wearing:
- Linen wide-leg pants (buttery cream or seafoam green)
- The Striped Palm nautical tee, untucked with a half-tuck flair
- Vintage sunglasses + a straw sun hat
- Minimalist sandals

SHOP THIS LOOK ON LTK: https://liketk.it/5eAqE
She writes poems in her notes app and lets the ocean air decide how her hair will look. This look feels like Sunday mornings by the harbor—quiet, polished, and deeply romantic.
📍 Perfect for: boat days, farmers markets, long journal entries with a lavender latte.
3. The retro time traveler
What she’s wearing:
- High-rise denim shorts
- Patriotic striped Striped Palm tee
- Red bandana tied with attitude
- Platform espadrilles + oversized hoop earrings

SHOP THIS LOOK ON LTK: https://liketk.it/5eAQ6
If you’ve ever wanted to time-travel back to a ‘70s seaside boardwalk, she’s already there (#inspo: vintage postcards and Kodachrome). This outfit’s all about adding bold, storybook details to a minimal silhouette.
📍 Perfect for: record store browsing, ice-cream cone selfies, retro diner lunches.
4. The cool girl at the country club
What she’s wearing:
- Open cardi + Striped Palm golf graphic tee
- Tailored khaki shorts (think buttery champagne tones)
- Loafers with hidden socks
- Monogrammed tote, possibly full of magazines + lemon water

SHOP THIS LOOK ON LTK: https://liketk.it/5eBJM
She blends classic and curated with vibes that say “I brunch here often” without trying too hard. You’ll find her flirting with a crisp G&T and winning every lawn game like she wasn’t even trying.
📍 Perfect for: garden luncheons, lawn parties, spontaneous croquet tournaments.
5. The preppy artist-in-residence
What she’s wearing:
- Wide-leg painter’s pants (ideally with actual paint splatters)
- Striped Palm tee with a pickleball paddle or crest
- Oversized linen blazer with rolled sleeves
- Hand-painted canvas tote + slightly messy bun

SHOP THIS LOOK ON LTK: https://liketk.it/5eC6A
Art school meets yacht club. She’s bold, highly specific about fonts, and maybe a little obsessed with blush pink. This look nods to prep tradition but breaks all the right rules.
📍 Perfect for: gallery nights, studio loafing, coastal bookstores with espresso on tap.
💡 The Takeaway: Casual Summer Outfits
Preppy style doesn’t have to be stiff, and personal style doesn’t have to follow every trend to feel current. The sweet spot? Somewhere between heritage and whimsy—with a graphic tee that tells your story, whether it’s “I play pickleball in pearls” or “My outfit has a playlist.”
With just a few standout pieces (hello, Striped Palm tees), you can build a summer wardrobe full of charm, personality, and casual character. The kind of looks that say:
“I dress like it’s golden hour… even when it’s Tuesday.”
✨ Feeling inspired?
Explore our Preppy Line of graphic tees here, where varsity fonts, coastal crests, and a dash of nostalgia meet your dream summer outfits.
We’ll meet you on the court. Or better yet, the dock.