20 Stylish Preppy Outfits For Men In 2025

Looking to up your style game in 2025?

Preppy outfits are making a major comeback, combining classic aesthetics with modern flair.

From tailored blazers to brightly colored chinos, this collection features 20 stylish preppy outfits for men that you can easily mix and match to create your perfect look.

Get inspired and step out with confidence!

Patterned Tie with Casual Blazer

preppy outfits for men

A patterned tie can really spice up a casual blazer look. It adds some personality while keeping things classy. This combo is perfect for both work and social events, making you stand out in a stylish way.

Tailored Blazer with Printed Shirt

A man wearing a tailored blazer over a printed shirt, looking stylish with sunglasses.

A tailored blazer over a printed shirt creates a sharp yet relaxed look. This combo works great for both casual outings and slightly dressier events. Pair it with some stylish sunglasses for that extra flair!

V-neck Sweater with Collared Shirt

Man in a brown V-neck sweater over a collared shirt, surrounded by autumn leaves.

The V-neck sweater paired with a collared shirt is a classic look that never goes out of style. This combination is perfect for layering, giving you a polished yet relaxed vibe. Choose warm, autumnal colors to fit right in with the season’s aesthetic!

Cable Knit Sweater Over Button-Up

A man sipping coffee while wearing a cable knit sweater over a button-up shirt.

Layering a cable knit sweater over a button-up shirt is a fantastic way to combine comfort and style. This look fits perfectly for any casual outing or relaxed office day. Pair it with chinos or jeans for an effortlessly preppy vibe that’s both cozy and chic.

Classic Polo Shirt and Chinos

A man wearing a gray polo shirt and beige chinos, standing outdoors in a park.

The classic polo shirt paired with chinos is a timeless look that never goes out of style. This combo is perfect for casual outings or smart-casual events, offering comfort without sacrificing style. Whether you choose a fitted polo or a relaxed fit, this outfit will keep you looking sharp in 2025.

Chino Shorts and Boat Shoes

A man walking on a boardwalk wearing striped shirt, chino shorts, and boat shoes.

Chino shorts paired with boat shoes create the perfect laid-back yet stylish look for warmer days. This combo is great for casual outings or beach trips, keeping you cool and comfortable. Add a fun, striped shirt, and you’re ready to turn heads while enjoying the sunshine!

Corduroy Pants with a Flannel Shirt

A man sitting casually in a cozy setting, wearing corduroy pants and a flannel shirt.

Corduroy pants paired with a flannel shirt create a cozy and stylish look that’s perfect for any casual outing. The texture of the corduroy adds depth, while the flannel brings a laid-back vibe. This combo works well in various settings, making it a go-to choice for 2025.

Graphic Tee and Tailored Shorts

A young man wearing a graphic tee and tailored shorts, engaged in conversation.

Rocking a graphic tee with tailored shorts is the ultimate combo for a relaxed yet stylish vibe. This look strikes the perfect balance between comfort and sophistication, making it great for casual outings. Pair it with sneakers or loafers, and you’re ready to turn heads without even trying!

Classic Denim Jacket and Khakis

A stylish man wearing a denim jacket and khaki pants, leaning against a vintage car.

The classic denim jacket paired with khakis is a timeless look that never goes out of style. This combo strikes a perfect balance between casual and polished, making it great for various occasions. Whether you’re meeting friends or heading to a casual event, this outfit is sure to make a solid impression.

Argyle Sweater Vest and Dress Pants

A man wearing a stylish argyle sweater vest over a blue dress shirt, paired with dress pants.

The argyle sweater vest paired with dress pants is a classic look that’s making a comeback in 2025. This outfit strikes a balance between relaxed and polished, perfect for both casual outings and slightly formal events. Add a button-up shirt underneath, and you’re all set to turn heads with your preppy style.

Wool Overcoat with Smart Casual Ensemble

A stylish man wearing a wool overcoat over a smart casual outfit, walking confidently.

A wool overcoat adds a sophisticated touch to any smart casual outfit. Pair it with a fitted blazer, a crisp shirt, and tailored trousers for an effortlessly chic look. This combination is perfect for a day at the office or a night out with friends.

Linen Suit for Summer Events

Man in a linen suit holding a drink at a summer event

A linen suit is a perfect choice for summer events. Its lightweight fabric keeps you cool while looking sharp. Pair it with a light shirt and a tie for a stylish finish.

Polo Shirt with Tailored Shorts

A man wearing a colorful striped polo shirt and tailored blue shorts, enjoying a picnic.

A polo shirt paired with tailored shorts is a classic preppy look that never goes out of style. This combination is perfect for a casual day out or a picnic with friends, blending comfort with a touch of sophistication. To add a retro flair, choose vibrant colors or patterns that nod to vintage aesthetics, making this outfit stand out while keeping it fresh and modern.

Classic Blazer with Chinos

Man wearing a classic blazer with chinos, embodying preppy style.

A classic blazer paired with chinos creates a stylish, preppy look for modern men. This combination can easily transition from casual outings to semi-formal events, offering versatility without sacrificing style. To add a vintage touch, consider a blazer with subtle patterns or colors reminiscent of retro styles.

Cardigan and Button-Up Combo

Man wearing a brown cardigan over a light blue button-up shirt, sitting thoughtfully.

The cardigan and button-up combo is a classic look that never goes out of style. This outfit gives off a relaxed yet polished vibe, making it perfect for various occasions. Mix in a few retro and vintage preppy styles, and you’ll instantly elevate your wardrobe with a timeless twist.

Sweater Vest with Dress Shirt

Man wearing a patterned sweater vest over a dress shirt, standing in a library setting.

A sweater vest paired with a dress shirt is a classic choice for modern men. This combo has vintage vibes, bringing a touch of retro style to your wardrobe. It’s perfect for both casual and slightly dressier occasions, making it versatile and stylish.

Nautical Stripes and Boat Shoes

A man wearing a striped shirt standing by the ocean

Nautical stripes are a classic choice for a preppy look that never goes out of style. Pairing a striped shirt with boat shoes gives a laid-back vibe that’s perfect for warm days. This combo brings together a few retro and vintage preppy styles for modern men, making it a great option for casual outings.

Seersucker Suit for Summer Events

A man in a stylish seersucker suit with a navy tie, standing outdoors with string lights.

A seersucker suit is a fantastic choice for summer events. Its lightweight fabric keeps you cool while still looking sharp. Pair it with a classic tie and some loafers for a touch of retro preppy style!

Houndstooth Patterned Blazer

A man wearing a houndstooth patterned blazer with a gray shirt, looking stylish and confident.

The houndstooth patterned blazer is a standout piece in any preppy wardrobe. This classic design adds a touch of sophistication while still feeling relaxed. Pair it with chinos or dark jeans to nail that retro vibe, perfect for modern men looking to blend vintage styles with contemporary flair.

Chino Pants with Oxford Shoes

A man walking confidently in a smart outfit featuring chinos and Oxford shoes.

Chino pants paired with Oxford shoes create a classic preppy look that’s perfect for any occasion.

This combo is not only stylish but also comfortable, making it a go-to choice for modern men.

Read Also: 10 Stylish Outfit Ideas for Men on a First Date

Incorporating a few retro and vintage preppy styles can add a unique flair to your outfit.