Ultimate Preppy Style for Men [2025]: 7 Tips and Icons to Inspire Your Look

The preppy style is a timeless trend in men’s fashion that started in East Coast universities and country clubs. For many decades, people have loved it for its sophisticated and refined appearance. When I tried it, I found that its key elements made my everyday wardrobe look simple and stylish. A helpful guide showed me how to explore its origins and use essential pieces that feel cleaner and fit my personal style. Preppy style for men has evolved into a dynamic and versatile fashion trend in 2025, the roots of the trend started with the return of preppy fashion.

“Preppy never goes away.” — Michael Bastian

Lisa Birnbach’s official Preppy Handbook (1980) became the definitive guide that defined the rules of preppy style for both men and women. It played a crucial role in shaping my approach to this timeless look.

The preppy style for 2025 is modern and fresh, blending classic elements with contemporary flair. Brands like UNIQLO and JW Anderson offer stylish spring and summer outfits that include timeless pieces like Oxford shirts, denim jeans, and polo shirts. Add fun accessories like neckties, caps, and nautical bags to bring a bright, cool vibe to your look. This style is easy to wear, fun to mix, and perfect for any occasion.

Preppy style comes from the look of students at preparatory schools on the East Coast of the United States. It is a mix of refined and laid-back fashion. This style is inspired by the Ivy League schools and includes classic shapes and tailored fits, which make the clothes both neat and comfortable.

Preppy style began in the 1890s as a symbol of Ivy League privilege, featuring button-downs, knit sweaters, and loafers. By the 1950s, it became mainstream with rugby shirts and plaid, evolving in the 1980s through brands like Tommy Hilfiger and icons like Princess Diana. The 2000s saw bold updates with bright colors and sparkle, while today’s designers like Ralph Lauren and Chanel mix argyle, plaid, and neck ties, keeping preppy modern and timeless. The style is always elegant, giving a timeless and cool vibe. If you’re wondering, “Do I want to look sharp, but not stuffy?” then preppy is the perfect answer.

“I’m very choosy, which is why I haven’t played the typical role that people expect to see from someone of my stature and size, as the mean jock or the preppy.” — Kellan Lutz

Preppy style began in the mid-1900s, inspired by Ivy League schools and the upper class in the Northeast. I remember movies like The Great Gatsby and characters like Blair Waldorf from Gossip Girl, who showed this neat and classy look. This timeless fashion is still popular and inspires men’s outfits today. Want to look cool like a skater? Skater boy style is all about feeling free, having fun, and dressing your best.

“The preppy lifestyle has gone global.” — Tommy Hilfiger

When you think of preppy fashion, you probably picture tailored outfits with soft pastel colors. Maybe you imagine classic khaki pants and a nautical striped shirt. There are so many combinations that create this style. By building a good wardrobe, you can start creating timeless looks that show off your unique style. These ensembles are not only easy to wear but also represent the classic look that people love today.

“I’m a big shoe person. Sometimes I’ll be punky, the next day I’ll be preppy.” — Hannah Montana

A navy blazer is a timeless piece that elevates any men’s casual outfit and adds polish to a dressy look. It’s a versatile item that can easily make your style look more put together for various occasions.

Polo shirts are made of breathable piqué cotton and come in classic colors and fun stripes. It is an integral part of preppy menswear. You can wear them with a navy blazer for a fancy look or with chinos for something more casual. These shirts are great for building a preppy wardrobe because they are comfortable and always look good.

Chinos are a must-have in any preppy wardrobe. These trousers, made from twill fabric and often 100% cotton, are the foundation of classic style. While some chinos come in synthetic blends, the best options are still pure cotton. Brooks Brothers and other fine clothiers offer a wide selection of colors like khaki, which is popular in coastal culture. You can also explore other colors like navy and olive for a versatile look.

The rugby shirt, a classic British piece, has become a favorite for preps due to its bold, colorful stripes and white collar. This aesthetic perfectly aligns with other preppy clothing items, making it a staple in stylish wardrobes.

Button-down collars were first made by Brooks Brothers in 1896. They became popular for wearing dress shirts to look more casual. They have buttons on the collar points. People like to wear them with an iconic navy blazer and a repp tie. They are perfect for work or a night out. You can also wear crisp oxfords in light blue, white, or gingham.

“I love preppy style; I like J. Crew for guys.” — Olivia Culpo

Crewnecks, V-necks, and cardigans keep you warm and look great. Fair Isle knits and argyle sweaters are cool patterns, often seen in golf clothes. Cable knit sweaters made from cotton, wool, or cashmere are always in style. For a preppy wardrobe, try them with bow ties or Tennis and Cricket sweaters.

Pro tip: Preppy style is about quality over quantity. Choose timeless, well-fitting pieces that mix and match easily.

Chinos, cords, and GTH pants can elevate your outfit with well-fitting choices. For an obnoxious yet fun style, look for bright pants with bold embroidery featuring sailboats, anchors, lobsters, and frogs. Brooks Brothers calls it a game of chicken—be a daring dresser and embrace this variety of icons!

To achieve a preppy style, focus on classic colors like navy, white, and light blue as your staples. Adding pastels such as pale pink or yellow can bring some personality to your outfit. Neutral tones like cream and beige often dominate, but you can also incorporate accents of mint or peach for a fresh touch.

For a preppy style, classic stripes like seersucker, along with gingham and madras plaid, are excellent choices. These patterns add depth and detail to your look, offering a subtle touch to elevate the outfit. Plaid and stripes are perfect for making your preppy style stand out.

• Loafers: For a preppy style, start with loafers like penny loafers or boat shoes for their timeless versatility.
• Leather belt: Pair them with a brown leather belt to tie the outfit together.
• Watches: A classic timepiece with a leather band is a must-have accessory.
• Ties and Scarves: Add some repp stripes or woven patterns in your dress shirts and bow ties for special occasions to bring in preppy flair.
• Footwear: For a polished edge, opt for brogues or stick to loafers and boat shoes.
• Belts: Finally, a woven belt or leather belt finishes the look with a sharp and cohesive style.

To truly master the preppy look, make sure your clothes are perfectly tailored to your body. When your clothes fit well, it creates a polished and put-together appearance, showcasing clean lines that give off a refined vibe. Always ensure that the overall fit emphasizes structure, making sure you’re always looking your best.

Whether you’re at the boardroom, studying the books, or having fun at the bar, a preppy outfit will always have you covered. You can look classy and stylish no matter the place, making sure you always feel good and look great.

“I went through different looks. At one period, I was preppy because that’s how I grew up.” — John Waters 

Tommy Hilfiger’s aesthetic is recognized as a symbol of classic American style, preppy look, and modern flair. Exciting news about Tommy Hilfiger and preppy style in 2025! The Fall 2024 collection, called “New York Minute,“ is all about the classic American preppy look with a modern touch. It includes fancy fabrics, updated designs, and a mix of casual and dressy outfits. This collection gives the preppy style a fresh and trendy update for today’s fashion lovers.

“I knew exactly what I wanted to do. I wanted to build some kind of lifestyle brand that was preppy and cool.” — Tommy Hilfiger

Below is the video guide on preppy style & clothes. Feel free to watch:

Prefer to read instead of watch? Here is the full video transcript for your convenience.

Outfit:

To keep it simple and neat, wear a polo shirt with chinos or khaki pants. Add boat shoes or loafers for a clean and finished style.

Accessories:

A leather belt and a classic watch are great accessories to make your outfit look better without doing too much. This is an easy way to look good and feel comfortable!

Outfit:

To look sharp and professional, wear tailored chinos with a button-down shirt in light blue or white. Add a blazer for extra style and a neat tie if it’s a formal event.

Accessories:

Keep it simple with a leather belt and watch for a clean and classy look.

Outfit:

For a casual brunch, wear an oxford shirt with a soft cardigan and comfy denim jeans. It’s a comfortable and stylish choice.

Accessories:

Keep it simple with minimal jewelry and a casual watch to add a refined touch to your look.

Outfit:

To make your style stand out, wear a button-down shirt with dark-wash chinos and a nice blazer.

Accessories:

Add Chelsea boots for a modern touch to your look, making it both cool and stylish.

Here are some of the top influencers and icons who have defined and continue to influence preppy style for men:

John F. Kennedy:

He helped make classic American style popular with clothes like khakis, Oxford shirts, and nautical-inspired pieces. He made preppy fashion a big deal in the 1960s.

Prince Charles (now King Charles III):

He is known as a preppy style icon. He wore traditional British clothes like tweed jackets, regimental ties, and well-tailored suits.

Steve McQueen:

He is an iconic actor and race car driver, who gave preppy style a more rugged and refined edge.

Eduardo Valderrama:

Eduardo Valderrama is a Fashion & Creative Consultant who mixes classic and trendy fashion. He combines timeless pieces with cool, new touches, like the socks and shorts in this outfit. People love his style, and he’s a big inspiration for anyone wanting to try preppy fashion!

Photo credit: @mrwhospain

“Preppy? Not me mate, I like the street look.” — Idris Elba

If you want to look preppy, brands like Ralph Lauren and Barbour are perfect for you. They have the best preppy clothes that give you a stylish and classic look. These preppy clothing brands help you stock your wardrobe with clothes that match the preppy fashion style. There are also women’s preppy clothing brands that offer clothes in the same great style!

• Ralph Lauren: Ralph Lauren has stylish clothes like Polo Ralph Lauren that look sophisticated but also casual. Their clothes have a simple, elegant style and often look sporty. Try the Plaid Tweed Double-Breasted Jacket with a button-down shirt and trousers for a classy look. For something lighter, the Logo-Crest Knit Blazer has a great fit and their famous logo on the breast pocket.

“I came from a private school, and public high school was the first time I ever went to a public school. So I went into it very preppy.” — Cassadee Pope

• J. Crew: When you’re building a preppy wardrobe, finding a go to brand that offers classic pieces at reasonable prices is key. Look for staples like tailored shirts, chinos, and casual blazers that can mix and match with ease. These reliable options ensure you stay stylish without breaking the bank.
• Barbour: Barbour is a luxury British brand that makes high-quality jackets and shoes with premium materials. Their best-selling jackets are great for hiking, fishing, and farming. One of their popular jackets, the Classic Beadnell, is a slim coat that keeps you dry in bad weather. For warm days, you can wear the Ella Striped Mini Dress with soft leather shoes for a striking look.
• Brooks Brothers: Brooks Brothers is known for its timeless clothes that are made with high-quality materials. The pieces they sell are built to last for many years. If you want something classic and stylish, this brand is a great choice for any preppy wardrobe.

The preppy style is a timeless trend that started with East Coast university culture. It mixes sophistication with a laid-back elegance and still looks great in 2025. Inspired by Ivy League fashion, iconic brands, and people like John F. Kennedy and Tommy Hilfiger, this style is easy to copy with key pieces like navy blazers, polo shirts, chinos, and Oxford button-downs. Adding classic accessories like loafers and leather belts helps show your personality. This look is about tailoring, simple shapes, and minimalism, so it works for any occasion. With a mix of modern updates and timeless elements, the preppy style makes you feel like the best version of yourself. It’s a polished and relaxed look that proves you don’t need to follow every trend to feel confident.

For daily preppy style inspiration – follow @mensminimal90 on Instagram, @MensMinimal on Youtube and @mensminimal on Pinterest! Join us for endless cute outfit ideas and aesthetic tips.

Dress preppy by wearing tailored outfits in soft pastel colors, such as khaki pants and a nautical striped shirt. Build a wardrobe with timeless looks that show off your unique style. These outfits are easy to wear and represent the classic preppy look that is still loved today.

Preppy today isn’t just about Ivy League schools; it’s more like a style or vibe. It mixes classic clothing, like blazers and polos, with a casual, modern touch. It’s not about strict rules but looking neat and stylish in an easy way. Being preppy now is about having a polished yet relaxed look that anyone can try.

To dress preppy in warm weather, choose light fabrics like cotton and linen, these materials allow air to flow, keeping you cool. Short-sleeve polo shirts or lightweight button-down shirts are great options. Pair them with chino shorts in soft or light colors for a relaxed yet stylish look. Loafers or boat shoes without socks work well for shoes. Add sunglasses and a leather belt to make the look neat and stylish. This style helps you stay cool and comfortable in the heat while looking good.

When building a preppy wardrobe, pick good-quality clothes that can be mixed and matched for a neat look. Thrift stores or secondhand shops can have great clothes, and they are usually cheap. You can find clothes with a special touch for your style.

Preppy style is about quality, not expensive brands. It’s focused on durable, well-made clothing that fits well and lasts. While some preppy pieces can be costly, buying second-hand or finding good deals at thrift stores is a smart option. The main goal is to invest in clothing that lasts and stays stylish, not just expensive brands.

Yes – preppy style is timeless! It’s a facet of classic style that has been around since the early 1900s and has endured for many years since.

If someone calls you “preppy,” it usually means that your style of dress looks neat, classic, and polished. Being called preppy is typically a compliment, as it means you are dressed in a way that follows this well-known, timeless style.