5 Classic Preppy Haircuts Any Guy Can Pull Off!

by Welcome to Outsons
Men in sunglasses with brown bag over his shoulder

Love it or hate it, the preppy style is a classic, with some of the most popular men’s hairstyles coming from this refined subculture. So, dust off your boat shoes and that pastel shirt – we’re here to show you some of the best preppy haircuts for men, as well as some of the various ways you can style them. 

#1: Ivy League Haircut

The Ivy League haircut, sometimes called the Princeton haircut, is about as preppy sounding as you can get. Despite the name, however, you don’t need to own a yacht, spend your holidays in the Hamptons or even have a degree. You don’t even need a lot of hair, and an Ivy League haircut is a great style to go for if you’re struggling with thinning hair. You can also try a Princeton fade, which tapers out the sides a little more to disguise any thinning areas. 

It may look like one of the simplest short men’s haircuts out there, but there’s some subtle tapering and differences in lengths that make it stand out from more basic cuts. The sides should be kept fairly short, a little longer than a crew cut, with the top slightly longer, and the front of the top longer than that. Still with us? Basically, the Ivy League is like a crew cut with three different lengths, the longest being at the front, and the shortest being at the sides. 


#2: Side Parting

Many short hairstyles for guys tend to shy away from the side parting, preferring a less defined, unstructured look. However, if you’re going for preppy look, it’s all about the sleek refinement, and an accentuated side parting fits perfectly with the style. It’s pretty important to get the styling right though, especially if you don’t want to go for the super slicked down look.

To ensure it stays one of the more stylish men’s haircuts out there, have your barber cut in the parting to keep it defined and easier to style. Then apply a light wax – anything too heavy will leave you with a heavy, greasy finish, and comb the front part of your hair back a little, leaving you with a sleek wave.  


#3: Curtain Fringe

One of the slightly…different hairstyles for men, and definitely not everyone’s favourite, the curtain fringe is staple preppy hairstyle and one that, when styled correctly, can be a great statement cut. Made popular, as well as infamous, in the 90s, the curtain fringe comes in various lengths but remains a refined yet wispy cut that suits a range of hair types. 

This is a great hairstyle for guys with short hair who are looking to grow it out and don’t know how to manage the awkward in between length. Because the curtain fringe can work with chin length hair to hair just above the ears, it’s a hairstyle that you can pretty much just style a bit and then leave alone. Whether you’ve got thick curls or fine straight hair, as long as you define the center parting and you’ve got even length on either side, then you can’t go too wrong. 


#4: Slicked Back

This next look might not be an everyday type of haircut for men, but sometimes slicked back hair is just the best option and can provide an elegant finish to a smart ensemble. They’re no real rules on making this hairstyle work for you, except the obvious ones. To make this male haircut work for you, your hair needs to be long enough to sweep back, but not so long that it can’t be styled.

Your hair should preferably be thick enough to give a bit of volume when slicked back, but not so thick that you’re going to need a whole tin of wax to keep it in place. It makes sense then that this is the best hairstyle for men with straight, medium thick hair, and you can go as light or extreme as you like with how you style it. Give it a bit of a pompadour look with a voluminous front, or slick the hair down completely for a classic, sleek finish.


#5: Curls or Waves

So far, preppy guys haircuts tend to be fairly structured and neat, with the classic Ivy League haircut for men showcasing this perfectly. However, a preppy look doesn’t necessarily have to fit into this business-like style, and those of you with a variety of curls can pull off this unstructured look. Chin length curls, or even soft waves, styled to work with the texture of your hair is one of the best haircuts for men who like a slightly less defined look. 

If you’re working with tight curls you can opt for a chin length style that will give them enough breathing space to not frizz up but will enable you to style them without too much trouble. Softer, wispier waves can be left to grow to a longer length, creating a relaxed men’s haircut style that gives off a clean, yet unrefined finish. Give it more structure with a clean parting, or go for a relaxed look with a swept back, invisible parting look. 


5 Classic Preppy Haircuts

  • Ivy League Haircut – An awesome short hairstyle for those with thinning hair. Short at the sides, with a long swept back parting.
  • Side Parting – Defined parting with sleek sides.
  • Curtain Fringe – Center parting with even sides.
  • Slicked Back – Works best with manageable, medium thick hair.
  • Curls or Waves – Unstructured, with an emphasis on a relaxed finish.

preppy haircuts for men look

On That Note

So, we’ve shown you some of the top hairstyles for men who enjoy the preppy look, with certain ones embracing the classic, formal style, and others opting for the new styles haircuts for men that take on a more relaxed, modern approach. Make sure you’re choosing a hairstyle that works with the texture and curl of your hair, and remember to keep your locks styled with good quality products. 

Feature image from Pinterest

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