25 Preppy Hairstyles for Men That Are Sharp, Timeless & Easy to Style

Preppy hairstyles have stood the test of time, offering men a clean, polished, and effortlessly stylish look. Inspired by Ivy League fashion and classic American grooming, these hairstyles are perfect for both casual and formal settings. Whether you’re headed to the office, a weekend brunch, or a special event, preppy cuts give you a sharp, well-groomed appearance with minimal effort.

This guide showcases 25 preppy hairstyles for men that combine timeless appeal, modern versatility, and easy styling for a sophisticated, put-together vibe.

25 Preppy Hairstyles for Men In 2025

1. Classic Side Part

The quintessential preppy hairstyle that never goes out of style.
Key Features: Defined part, neatly combed sides, clean finish.
Styling Tips: Use a fine-tooth comb with lightweight pomade for a sleek look.
Best For: Straight or wavy hair.
Vibe: Elegant, traditional, and versatile.

2. Ivy League Cut

A polished cut with slightly more length on top for styling options.
Key Features: Short, tapered sides with a neatly combed top.
Styling Tips: A touch of styling cream adds natural shine and volume.
Best For: Oval and square face shapes.
Vibe: Classy, intellectual, and timeless.

3. Tapered Comb Over

A modern twist on a classic preppy look, ideal for formal settings.
Key Features: Gradual taper fade, top combed neatly to one side.
Styling Tips: Keep the part defined with light-hold gel.
Best For: Professional and semi-formal events.
Vibe: Sharp, sophisticated, and clean.

4. Slicked-Back Style

A refined, gentlemanly look for special occasions or daily wear.
Key Features: Medium-length hair combed straight back with a glossy finish.
Styling Tips: Use pomade for shine or matte cream for a softer effect.
Best For: Men with straight or thick hair.
Vibe: Confident, suave, and timeless.

5. Short Textured Crop

An easy-to-maintain preppy hairstyle with a modern edge.
Key Features: Short, layered top with natural texture.
Styling Tips: Apply matte clay for a casual, tousled finish.
Best For: Thinning or fine hair types.
Vibe: Youthful, fresh, and low-maintenance.

6. Brushed-Up Quiff

Adds subtle height while maintaining a neat, preppy finish.
Key Features: Lifted front with cleanly tapered sides.
Styling Tips: Use a blow-dryer and light mousse for controlled volume.
Best For: Medium to thick hair textures.
Vibe: Sharp, elegant, and photo-ready.

7. Crew Cut with Defined Part

A military-inspired classic turned preppy favorite.
Key Features: Ultra-short sides, slightly longer top with a crisp part.
Styling Tips: Minimal product needed, just a quick comb-through.
Best For: Busy men who want simplicity.
Vibe: Masculine, neat, and structured.

8. Side-Swept Fringe

A softer preppy look that frames the face beautifully.
Key Features: Longer top layers brushed to one side, tapered sides.
Styling Tips: Use a light styling cream for a natural, touchable finish.
Best For: Men with straight or slightly wavy hair.
Vibe: Refined, approachable, and stylish.

9. Medium-Length Layered Flow

Perfect for men who like a bit of movement in their hairstyle.
Key Features: Longer top and back, layered for natural flow.
Styling Tips: Apply leave-in conditioner for smooth, frizz-free movement.
Best For: Wavy or straight thick hair.
Vibe: Relaxed, classy, and effortless.

10. Low Fade with Side Part

A modern preppy look that combines sharp fades with classic styling.
Key Features: Clean low fade, neatly parted and combed top.
Styling Tips: A small amount of pomade keeps it neat all day.
Best For: Men who like a polished, contemporary look.
Vibe: Trendy, sophisticated, and crisp.

11. Brushed-Forward Layers

Adds softness and structure while staying neat and professional.
Key Features: Short layers brushed toward the front.
Styling Tips: Use matte wax for natural hold and texture.
Best For: Men with fine or thinning hair.
Vibe: Understated, smart, and well-groomed.

12. Short Pompadour

A preppy take on the classic pompadour for a gentlemanly vibe.
Key Features: Lifted top with tapered sides.
Styling Tips: Use strong-hold mousse for volume that lasts all day.
Best For: Men with thick hair who like a polished look.
Vibe: Bold, refined, and confident.

13. Comb Over with Hard Part

Adds definition and edge to the traditional preppy style.
Key Features: Clean shaved part with neatly combed top.
Styling Tips: Keep the part sharp with regular barber visits.
Best For: Medium-length straight hair.
Vibe: Crisp, modern, and stylish.

14. Short Side Fade

Minimal yet preppy, perfect for men who prefer simplicity.
Key Features: Very short sides with neatly trimmed top.
Styling Tips: Requires almost no product, just a fresh cut every few weeks.
Best For: Men with active lifestyles.
Vibe: Clean, masculine, and timeless.

15. Wavy Side Part

Embraces natural waves for a soft yet refined style.
Key Features: Defined part, slightly tousled waves.
Styling Tips: Use sea salt spray for texture and natural hold.
Best For: Medium-length wavy hair.
Vibe: Relaxed, classic, and approachable.

16. Gentleman’s Buzz Cut

Short, even length with a tailored, preppy finish.
Key Features: Close-cropped cut that looks intentional and sharp.
Styling Tips: Keep hairline clean with regular trims.
Best For: Men who prefer ultra-low-maintenance grooming.
Vibe: Strong, neat, and minimalistic.

17. Side Part with Volume

Combines classic parting with subtle lift for a modern look.
Key Features: Slightly longer top, clean fade, brushed up at the front.
Styling Tips: Use volumizing powder for a natural, matte effect.
Best For: Oval and square faces.
Vibe: Elegant, contemporary, and versatile.

18. Slicked Side Fade

Perfect for formal events or professional settings.
Key Features: Tight fade on the sides, sleek combed styling on top.
Styling Tips: Apply medium-hold gel for a smooth, glossy look.
Best For: Straight hair textures.
Vibe: Sophisticated, mature, and dapper.

19. High Taper with Brushed Top

Adds a modern, fresh feel to the traditional preppy aesthetic.
Key Features: High taper fade with a clean, brushed-up top.
Styling Tips: Light mousse or wax for a polished, natural look.
Best For: Men wanting a youthful, sharp vibe.
Vibe: Contemporary, stylish, and sharp.

20. Layered Medium Cut with Natural Part

Lets hair fall naturally for an effortless preppy charm.
Key Features: Layers softly parted for a casual yet refined look.
Styling Tips: Use a light styling cream to keep strands in place.
Best For: Wavy or straight thick hair.
Vibe: Relaxed, classy, and easygoing.

21. Low Fade with Slick Back

A clean, modern haircut that stays sharp all day.
Key Features: Fade on the sides, longer slicked-back top.
Styling Tips: Use pomade for high-shine or matte wax for a natural finish.
Best For: Medium to thick hair.
Vibe: Smart, confident, and classic.

22. Textured Ivy Sweep

Adds youthful energy to a classic Ivy League style.
Key Features: Slightly tousled top, soft taper on sides.
Styling Tips: Work matte paste through hair for a textured finish.
Best For: Men in need of a casual yet professional style.
Vibe: Fresh, modern, and preppy.

23. Crew Cut with Line-Up

A sharp, clean preppy hairstyle with well-defined edges.
Key Features: Short length with precision hairline.
Styling Tips: Touch up the edges regularly for a polished look.
Best For: Any hair type or face shape.
Vibe: Neat, strong, and timeless.

24. Preppy Long Fringe

Longer front layers create a soft, modern preppy effect.
Key Features: Side-swept fringe with tapered sides.
Styling Tips: Blow-dry lightly and use a bit of styling cream for flow.
Best For: Men with straight or slightly wavy hair.
Vibe: Youthful, charming, and stylish.

25. Gentleman’s Flow Back

Medium layers styled back for a natural yet sophisticated vibe.
Key Features: Hair flows neatly with soft movement, minimal product needed.
Styling Tips: Use leave-in conditioner for smooth, healthy shine.
Best For: Longer hair with natural body.
Vibe: Relaxed, elegant, and effortlessly preppy.