Preppy fashion never goes out of style.
It’s all about blending classic pieces with modern touches to create outfits that look sharp and polished.
From tailored blazers to cozy cable-knit sweaters, preppy outfits are versatile for any occasion, whether casual or formal.
In this guide, I’ll show you 23 preppy outfits for men that look stylish and help you stand out wherever you go.
1. Classic Navy Blazer with Khaki Pants
Embrace the timeless preppy style with a navy blazer and khaki pants. The crisp white shirt and patterned tie bring elegance, while brown loafers and a leather satchel add classic charm. Perfect for a polished yet approachable look, this outfit is ideal for campus strolls or casual business meetings. Ivy-covered walls and vintage details amplify the collegiate vibe.
2. Argyle Sweater with White Chinos
Channel effortless preppy charm with an argyle sweater and white chinos. The layered light blue shirt and tan loafers bring a touch of refinement, while the braided belt ties the look together. Set against a serene park with autumn leaves, this outfit balances sophistication and a relaxed outdoor vibe. Ideal for casual gatherings or weekend outings.
3. Button-Down Shirt with a Sweater Vest
Elevate your style with a burgundy sweater vest layered over a crisp button-down. Grey trousers and brown brogues offer a polished finish, while a wool scarf adds warmth and sophistication. The round glasses and classic stone architecture in the background evoke an intellectual, scholarly vibe, perfect for library visits or casual professional settings.
4. Navy Polo with White Shorts
Achieve a timeless nautical look with a navy polo and white shorts. The boat shoes and woven leather belt add classic details, while aviator sunglasses enhance the preppy aesthetic. Perfect for a day by the marina, this outfit offers both comfort and style. The serene yacht-filled backdrop completes the summer vibe effortlessly.
5. Cable-Knit Sweater with Plaid Trousers
Stay cozy and stylish with a cream cable-knit sweater and plaid trousers. Dark brown boots and a newsboy cap enhance the preppy look with vintage flair. Ideal for chilly days, the outfit balances warmth and elegance. The rustic cabin backdrop and wintry details make it a perfect choice for casual outdoor gatherings.
6. Striped Rugby Shirt with Dark Jeans
Sporty and casual, this striped rugby shirt paired with dark jeans is a preppy wardrobe staple. White sneakers complete the laid-back look, while the leather duffel bag adds a touch of practicality. Perfect for weekend errands or casual outings, the schoolyard backdrop enhances its youthful, athletic charm.
7. Pastel Pink Oxford Shirt with Beige Chinos
Add a touch of softness to your wardrobe with a pastel pink oxford shirt paired with beige chinos. The brown loafers and gold watch elevate the outfit, making it versatile for garden parties or casual lunches. The blooming flowers and sunny patio backdrop enhance the light, sophisticated vibe.
8. Double-Breasted Blazer with White Pants
For a classic yet striking look, opt for a double-breasted blazer with white pants. The gold-button detailing and pocket square exude sophistication, while tan loafers keep it grounded. Perfect for formal events, the elegant staircase and grand backdrop emphasize this polished preppy style.
9. Crewneck Sweater with White Collared Shirt
Layered perfection comes to life with a crewneck sweater and collared shirt. Navy chinos and brown loafers keep the look polished yet comfortable, making it ideal for casual days out. The leather messenger bag adds a functional touch, while the autumn park setting enhances the relaxed sophistication of this outfit.
10. Navy Peacoat with Wool Scarf
A navy peacoat paired with a wool scarf delivers timeless winter sophistication. Tailored black trousers and Chelsea boots complete the polished urban look, while the leather briefcase adds a professional edge. Perfect for brisk city days, this outfit shines against the vibrant backdrop of skyscrapers and bustling streets.
11. Preppy Cardigan with Checked Shirt
Stay cozy and stylish with a preppy cardigan over a checked shirt. Paired with dark jeans and suede boots, this outfit is perfect for chilly mornings or weekend strolls. The vintage bicycle and cobblestone alleyway add a rustic charm that complements the laid-back, preppy aesthetic effortlessly.
12. Seersucker Suit with Loafers
For a refined summer style, try a seersucker suit paired with a bow tie and loafers. This light and airy outfit is ideal for garden parties or outdoor weddings. The straw hat adds charm, while the gazebo and vibrant garden backdrop amplify the timeless preppy elegance of this look.
13. Camel Trench Coat with Turtleneck
Exude sophistication with a camel trench coat layered over a black turtleneck. Grey trousers and leather Oxfords create a sleek silhouette, perfect for rainy days in the city. The umbrella and briefcase add practical elegance, while the glowing streetlights and rainy reflections set a moody, stylish tone.
14. Preppy Gingham Shirt with V-Neck Sweater
Combine casual and polished elements with a gingham shirt layered under a V-neck sweater. Beige chinos and penny loafers bring a classic touch, perfect for relaxed brunches or coffee dates. The lively café setting adds a vibrant urban charm that matches this effortlessly preppy style.
15. Polo Shirt with Sweater Draped Over Shoulders
Embrace coastal preppy vibes with a polo shirt and draped sweater. Navy shorts and canvas sneakers keep it casual yet refined, ideal for seaside strolls or weekend getaways. The serene beach backdrop and minimalist accessories add a relaxed elegance to this stylish summer outfit.
16. White Cable-Knit Sweater with Khaki Pants
Nothing says classic preppy style like a white cable-knit sweater paired with khaki pants. Perfect for chilly evenings by the fireplace, this outfit combines comfort and elegance. Brown moccasins and the cozy cabin ambiance add a touch of warmth and sophistication to this timeless winter look.
17. Striped Rugby Shirt with Slim-Fit Jeans
Channel sporty preppy vibes with a striped rugby shirt and slim-fit jeans. The white sneakers keep the look casual and dynamic, ideal for weekend outings or sports matches. The grassy field and goalposts enhance the active, stylish aesthetic of this outfit.
18. Tweed Blazer with Dark Denim
Achieve a scholarly preppy look with a tweed blazer paired with dark denim and brogues. This combination strikes the perfect balance between formal and casual, ideal for campus or cultural events. The library backdrop adds depth to this intellectual and timeless outfit.
19. Linen Shirt with Roll-Up Sleeves and Chinos
Opt for effortless preppy style with a linen shirt and chinos, perfect for sunny days by the water. Tan boat shoes and rolled-up sleeves keep the outfit relaxed yet polished. The marina backdrop, with its sailboats and sparkling water, enhances the breezy, coastal charm of this look.
20. Fair Isle Sweater with Corduroy Pants
Bring warmth and color to your winter wardrobe with a Fair Isle sweater and corduroy pants. Leather hiking boots and cozy accessories make it ideal for outdoor adventures. The snowy trail and scenic mountain backdrop perfectly capture the rugged elegance of this preppy outfit.
21. Black Turtleneck with Tailored Overcoat
Sophisticated and sleek, a black turtleneck paired with a tailored overcoat is the ultimate evening look. Slim-fit trousers and polished loafers complete the refined ensemble. The cobblestone streets and warm streetlamp glow enhance the timeless appeal of this preppy outfit, perfect for nights in the city.
22. Plaid Shirt with Puffer Jacket
Blend rugged and preppy styles with a plaid shirt and puffer jacket. Black cargo pants and hiking boots make it both functional and stylish for outdoor adventures. The vibrant autumn backdrop with golden leaves highlights the cozy and dynamic appeal of this fall-ready outfit.
23. Navy Blazer with Grey Trousers
Command attention with a navy blazer and grey trousers, a classic preppy combination for professional settings. Brown leather shoes and a silk tie add elegance, making it perfect for work or formal occasions. The modern office backdrop enhances the polished, confident appeal of this outfit.
Conclusion
Preppy outfits offer a perfect balance of elegance and comfort, making them a go-to choice for stylish men. Whether you prefer a classic blazer or a cozy sweater, these looks ensure you’re always on-trend and well-dressed.
