The Real Chic Life

The Ultimate Guide to Preppy Style: How to Dress Classic & Timeless

Recently I watched the gorgeous Ralph Lauren Spring 2025 fashion show that took place in the Hamptons, and I was reminded of how much I love classic, preppy style. Preppy style is a timeless fashion aesthetic that blends classic elegance with a touch of sporty sophistication. Originating from the Ivy League campuses of the early 20th century, this look has evolved while maintaining its signature elements: crisp tailoring, clean lines, and a polished yet effortless vibe. If you’re drawn to outfits that feel refined, put-together, and timeless, preppy style might be for you.

Here’s everything you need to know to embrace the preppy aesthetic with confidence.

1. Build a Classic Preppy Wardrobe

A preppy wardrobe is built on versatile, high-quality staples that never go out of style. Focus on well-tailored, structured pieces in a color palette of neutrals, pastels, and classic patterns like stripes and plaid.

Essential Preppy Clothing Pieces:

• Blazers – A well-fitted navy or camel blazer instantly elevates any outfit.
• Crisp Button-Down Shirts – Think white, light blue, or striped Oxford shirts, perfect for layering.
• Cable Knit Sweaters – Timeless and cozy, they look great draped over shoulders or layered over a collared shirt.
• Polo Shirts – A staple of preppy style, polos are both sporty and polished.
• Sweater Vests – A modern twist on classic prep, perfect for layering.
• A-Line & Pleated Skirts – Think tennis skirts or full poplin skirts for a preppy feminine touch.
• Chino Pants & Tailored Shorts – Opt for beige, navy, or pastel shades for a sophisticated yet relaxed look.
• Dark-Wash or White Jeans – Clean, slim-cut denim keeps your look polished.
• Trench Coats – A timeless outerwear choice that exudes sophistication.

2. Choose the Right Footwear

Shoes play a big role in achieving the preppy aesthetic. The key is to stick with classic, well-made styles that are both stylish and practical.

• Loafers – A staple of preppy fashion.
• Ballet Flats – Simple, elegant, and easy to wear with skirts or trousers.
• Boat Shoes – A casual yet polished footwear option, ideal for warm weather.
• White Sneakers – A modern prep essential that pairs well with everything from jeans to skirts.

3. Master Preppy Patterns & Colors

Preppy fashion embraces classic patterns and soft, sophisticated colors.

Signature Patterns:

• Stripes (Breton, rugby, or pinstripes)
• Plaid (especially gingham)
• Polka dots

Go-To Color Palette:

• Neutrals – White, navy, beige, gray, and black
• Pastels – Soft pinks, baby blue, mint green, and lavender
• Bold Classics – Red, hunter green, and mustard yellow for statement pieces

4. Keep Accessories Polished & Understated

Preppy accessories are refined, classic, and never over-the-top. A few key pieces can instantly enhance your look.

• Pearl or Gold Jewelry – Think pearl stud earrings, delicate gold chains, or signet rings.
• Headbands & Hair Bows – A signature preppy touch.
• Structured Handbags – Opt for leather totes, crossbody bags, or top-handle purses.
• Silk Scarves – Worn around the neck, tied to a bag, or as a hair accessory.
• Classic Sunglasses – Think wayfarers, cat-eye, or tortoiseshell frames.

5. Preppy Beauty: A Polished & Natural Look

The preppy beauty aesthetic is about looking fresh-faced, polished, and effortless.

• Minimal Makeup – A light base, soft blush, and a swipe of mascara.
• Natural Lips – Stick to tinted balms, nude glosses, or classic red lipstick.
• Well-Groomed Brows – Keep them neat but not overly sculpted.
• Glossy or Neutral Nails – French manicures, soft pinks, or classic red polish work best.

Preppy style is all about looking put-together, polished, and effortlessly chic. By investing in classic wardrobe staples, embracing timeless patterns, and keeping your beauty and accessories refined, you can embody this sophisticated aesthetic with ease.

Are you a fan of preppy fashion? Which pieces are your go-to?

Xo,

Courtney

P.S.- Don’t miss our seasonal update- The Real Chic Guide to Preppy Fall Style!