You know that guy at brunch who shows up in pastel chinos, a striped button-down, and boat shoes… yet somehow looks like he stepped out of a country club catalogue circa 1984? That’s the thing about preppy style: done wrong, you look uptight and out of place. Done right, you look like you woke up in a Nancy Meyers movie, texted your yacht captain, and decided to meet friends for champagne before noon. The trick is balance. Preppy doesn’t have to scream “trust fund energy”. It can feel modern, effortless, and cool if you know where to edit. Let’s break it down.
1. Forget Perfect. Aim for Relaxed Elegance
Old-school preppy is crisp and pressed. But modern preppy is less about starch and more about attitude. Think soft Oxford shirts with the sleeves slightly rolled. Chinos that skim, not strangle, your legs. Blazers cut sharp but unstructured enough to move with you.
When designer Thom Browne once reimagined Ivy League tailoring with shrunken proportions, people thought he’d broken the preppy code. He didn’t. He rewrote it. That’s the key. Today, preppy is about subtle rebellion. Skip the matchy-matchy vibe. Mix your khaki shorts with a vintage band tee, or wear your penny loafers with white socks and denim. Make it yours.
2. Play With Colour Without Going Full Rainbow Row
Preppy has always loved colour, but there’s a fine line between “playful” and “parody”. Pastels still work, but they shine when balanced with grounding neutrals. A mint-green polo? Perfect with white jeans and leather sandals. A salmon blazer? Best friends with crisp beige trousers.
French street-style star Simon Porte Jacquemus once said that the secret to wearing bold hues is making the rest of your outfit whisper. Let one piece speak loudly and keep everything else calm. That’s how you look intentional, not like you raided a golf club locker room.
3. Accessorize Like Someone Who Has Stories to Tell
Accessories separate the preppy novice from the preppy pro. But here’s the rule: avoid anything that screams “costume”. That braided leather belt your uncle wore in 1993? Retire it. Instead, go for timeless, textured accents: a woven bracelet from a summer in Mykonos, a leather-strapped vintage watch, or a baseball cap from that indie coffee shop in Lisbon.
The vibe? Effortless wealth of experience, not endless spending. You want pieces that say “I travel” without announcing “I booked business class just for the Instagram post.”
4. Mix Old Money With Street Energy
Here’s where the modern preppy renaissance is thriving. Labels like Ralph Lauren and J. Press have heritage locked down, but brands like Aimé Leon Dore and Noah are redefining what preppy looks like today. It’s rugby shirts paired with chunky sneakers. It’s cable-knit vests layered under bomber jackets. It’s an Ivy League soul with downtown energy.
Watch how stylists at Paris Men’s Fashion Week have been remixing preppy staples recently: cropped cardigans worn open, tennis whites turned into all-day uniforms, and loafers styled with basketball socks. There’s a freedom in bending the rules without breaking the aesthetic entirely.
5. Confidence Is the Real Outfit
The most preppy thing you can wear is self-assurance. The clothes are secondary to the energy you bring into a room. You can rock a vintage Lacoste polo or a thrifted blazer, but if you look like you’re auditioning for a role you don’t believe in, it’ll show.
Here’s a trick: pick one preppy staple you genuinely love and build around it. If it’s a striped Oxford, lean into it with casual linen trousers and sneakers. If it’s loafers, let them anchor your look while the rest stays modern. Ease is attractive, and attractive is always in style. And if you ever feel unsure, remember this: no one ever regretted a perfectly fitted blazer, a clean white shirt, or a good pair of loafers. The rest is just editing.
