Dress in the Ivy League: A Style Guide to the Best Preppy, Collegiate Brands

Rooted in Tradition

The Ivy League look didn’t just pop up overnight. It emerged from American East Coast campuses, where students combined casual comfort with a hint of formality. This style is anchored in history: think decades-old pictures of students wearing tweed blazers, wool sweaters, and well-polished loafers. These looks have been refined over the years, but they still hold that timeless, scholarly aura.

The resurgence of '80s preppy style owes much to the overwhelming popularity of shows like Monsters: The Menendez Brothers. While the gripping storyline captivates viewers, the standout preppy fashion takes center stage, especially as Lyle Mendendez was in his Princeton University days. The Menendez aesthetic lore is more iconic than ever.

If you too are fascinated by the preppy aesthetic and its 80’s revival, you’re in the right place. 

Fun fact: the word preppy emerged from Prep school culture and style, when prep school dominated education in the early 20th century, then the style was born inspired by collegiate uniforms and sporty co-ords for tennis, track, golf, rowing, croquet etc...

Quality Over Flash

Rather than focusing on flashy logos or over-the-top patterns, the Ivy aesthetic leans toward understated elegance. Fabrics and fits matter more than big brand names splashed across your chest. You might spot subtle patterns like stripes, checks, or understated crests, but nothing screams. The result is clothing that looks just as good now as it will in ten years—maybe even better with a bit of wear and history behind it.

Essential Pieces for an Ivy-Inspired Wardrobe

Building a preppy wardrobe isn’t about buying everything at once. It’s about selecting a few well-made staples and then layering in extras as you go. Here are the key pieces that often find their way into Ivy-inspired closets.

The Classic Polo

A polo shirt is almost the mascot of preppy style. It’s casual but not sloppy, comfortable but still neat. Usually crafted in breathable cotton, the polo can be paired with chinos or shorts. Stick to solid colors—navy, white, light blue, maybe a pale pink—shades that remind you of leisurely afternoons spent strolling across campus lawns.

Button-Down Shirts

A good button-down, especially one with a soft collar roll (the collar that arches gently), anchors many Ivy League outfits. White and blue are must-haves, but adding in a few stripes or subtle checks never hurts. These shirts fit well under blazers, sweaters, or just by themselves with rolled-up sleeves for a relaxed weekend look.

Blazers and Suits

A blazer can instantly raise your style game. Navy blazers are a classic choice, usually paired with dark muted tones. They match easily with chinos, dress trousers, and even well-fitted jeans for a modern twist. A good blazer frames the shoulders, skims the body, and can last for years if you invest in quality materials.

Chinos and Khakis

Forget skinny jeans—chinos and khakis are the real MVPs in an Ivy-inspired wardrobe. They’re comfortable, versatile, and work with just about any top. Look for pairs in neutral shades like tan, beige, navy, or stone. The fit should be tailored but not tight. You should be able to sit, walk, and maybe even toss a football on the quad without feeling restricted.

Sweaters and Cardigans

When the weather cools, a well-chosen sweater is your friend. Crewnecks, V-necks, and cardigans in wool or cotton bring warmth and style. Cable-knit patterns, argyle, and subtle stripes can add personality without going overboard. Wear them over a button-down and under a blazer, or toss one around your shoulders for a casual, effortless look.

Loafers and Other Footwear

Leather loafers and boat shoes practically define Ivy League footwear. They’re comfortable enough for all-day wear but polished enough for a dinner out. Keep them clean and well-maintained—these aren’t sneakers meant to be tossed around. If you prefer something more rugged, a pair of well-made boots can also fit in nicely, especially in the cooler months.

Accessories That Seal the Deal

Preppy style thrives on subtle details. A woven belt, a simple striped tie, a leather watch with a neutral strap—these items can pull an outfit together. Don’t overlook a good pair of socks. Argyle patterns or simple solids in natural fibers show that you pay attention to the small stuff. And if you really want to lean into tradition, consider a pocket square or a wool scarf.

The Best Brands to Channel Ivy League Style

Certain labels have shaped and sustained this aesthetic for decades. While you can find preppy pieces almost anywhere, these brands have well-earned reputations for delivering that collegiate feel.

Brooks Brothers

Brooks Brothers is practically synonymous with Ivy style. Their button-down shirts set the standard, and their suits, ties, and sweaters have dressed generations of college students, presidents, and cultural icons. If you want something that screams “classic East Coast,” this is a good place to begin.

J. Press

J. Press has roots in the Ivy League world going back over a century. They’re known for their sack suits (a jacket style without darts, giving it a slightly looser fit), classic ties, and wool blazers. Their clothes often feel like they’ve stepped out of an old photograph—reassuringly traditional.

Ralph Lauren

Ralph Lauren might have expanded into many style territories, but their early roots in preppy aesthetics remain. Polo shirts, chino shorts, cable-knit sweaters, and navy blazers—Ralph Lauren has it all. The brand’s signature horse-and-rider logo has become almost synonymous with a polished, collegiate vibe.

Abercrombie & Fitch

No conversation about the preppy aesthetic is complete without mentioning Abercrombie & Fitch. Once synonymous with collegiate cool and effortless American style, the brand defined the preppy wardrobe of the late ‘90s and early 2000s. With its iconic moose logo, crisp polos, cable-knit sweaters, and perfectly distressed denim, Abercrombie & Fitch became the go-to label for a generation embracing laid-back sophistication.

J.Crew

J.Crew often offers a more relaxed, modern approach to preppy style. Their chinos, blazers, and shirts might have slightly slimmer fits, appealing to those who want the Ivy League look with a contemporary twist. They’re great for blending traditional and modern pieces seamlessly.

Rowing Blazers

If you’re looking for something that breaks from standard traditions while still honoring them, Rowing Blazers is an option. They play with color, patterns, and sometimes bold stripes, referencing rowing clubs, rugby jerseys, and other sports historically linked to Ivy League universities. It’s preppy, but with a wink.

Sporty & Rich

Founded by Emily Oberg, a visionary with roots in streetwear and editorial design, Sporty & Rich began as a passion project and quickly cemented itself as a preppy-cool cultural staple.

At its core, Sporty & Rich champions timeless simplicity, impeccable quality, and a commitment to wellness. Its collections blend vintage-inspired aesthetics with modern sustainability, offering clean lines and effortlessly chic designs. With the motto “Be nice, drink water, be good to the planet,” the brand has become a favorite for those who value classic style paired with mindful living.

Lacoste

Lacoste popularized the polo shirt decades ago, and it still stands as a symbol of refined leisure. The small crocodile logo on a well-fitted polo is iconic. Pair it with chinos and boat shoes, and you’re channeling a style that works on the tennis court or at a weekend brunch.

Incorporating the Look into Everyday Life

Mixing and Matching

Preppy collegiate style doesn’t require you to wear a blazer 24/7. Mix dressier pieces, like a navy blazer, with more casual items, like jeans or a T-shirt. Blend a crisp button-down with a cable knit tied around your shoulders. The goal is to look effortlessly put-together, not as if you’re on your way to a board meeting.

Dressing for Different Seasons

This aesthetic adapts well across seasons. In spring and summer, go for lighter fabrics, pastel polos, and boat shoes. When the weather cools, layer sweaters, scarves, and wool coats. Don’t be afraid to experiment with seasonal colors—burgundies, forest greens, and browns in autumn; greys and navy blues in winter.

Caring for Your Clothes

Investing in quality pieces means you’ll want them to last. Follow the care instructions. Hang your blazers properly, fold your sweaters to maintain their shape, and polish your leather loafers now and then. Remember that wrinkles and slight wear can add character, so don’t stress over perfection. These clothes are meant to live with you, not just hang in a closet untouched.

Personalizing the Style

There’s no need to copy a look straight off a catalog page. Your version of the Ivy League aesthetic could include a favorite band’s pin on your shirt’s lapel or an elegant neckerchief that reflects your personality. Maybe you prefer a slimmer fit or you like to add a statement watch that reminds you of your grandfather’s old timepiece. Preppy style is a canvas, not a strict rulebook.

When done right, dressing in this collegiate manner can lend a sense of calm confidence to your everyday life. It suggests thoughtfulness and care, but without forcing the issue. It’s about embracing a heritage of quality, comfort, and understated class. Whether you’re heading to a meeting, a casual dinner, or simply enjoying a weekend coffee, these looks can help you feel ready for whatever comes your way.