Reviewed & updated: October 19, 2022 by Jamie Wilson BA
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. Are you looking for some new hairstyles? If you want to try out something new and done in layers, keep on reading. Here, we will list a ton of medium length to simple style hairdos. Find your next preppy hairstyle down below.
What Is A Preppy Haircut?
Looking for a list of versatile hairstyles that can all look preppy? Say no more, since you’re exactly where you need to be! When it comes to a preppy hairstyle, this is a haircut that is elegant and defined, as well as well taken care of. It is neat and always in style, along with being a fashionable statement. Men and women of all ages can try out this hairdo, and give it more so a casual look vibe. Aim for a preppy look if you:
- Want to have a good sporty hairstyle that stands out
- You are looking for an office look
- You want to look neat for your prom
This cut can work well on curly hair, wavy hair, or short hair. It all just comes down to customizing it per your face shape, texture, and casual style or workaholic vibe.
5 Classic Preppy Haircuts Any Guy Can Pull Off!
#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. It is one of those short haircuts that are very low maintenance + it can work well on thin 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. Basically, the Ivy League is like a crew cut with three different lengths, the longest being around your front portions, 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 a preppy look, it’s all about the sleek refinement, and accentuated side parting fits perfectly with the style. If you prefer wavy preppy hairstyles and you want to wear one half of your hair on the side, this look is for you.
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. This will leave your strands shiny and without frizzy hair.
#3: Curtain Fringe
One of the slightly…different hairstyles for men, and definitely not everyone’s favourite, the curtain fringe is a staple preppy hairstyle and one that, when styled correctly, can be a great statement cut. It is the next level haircut that looks wonderful when you have longer hair and as you spice it up with some beautiful tunics. 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. Apply a bit of your favorite texture spray to push the hair in your preferred direction.
#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. A ton of guys like to do this haircut for the winter season since it is such a chic look that can make you feel warm while being trendy.
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. If you have loose waves you can style them into new preppy hairstyles!
#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. This is where messy buns, braids, or wavy hair side pony looks can come in handy!
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.
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.