20 Best Old Money Hairstyles: A Timeless Elegance

This is the title image of the article about timeless old money hairstyles.

When thinking of old money individuals, their unique old money hairstyles catch the eye very fast. Resembling elegance and timelessness, these haircuts are classic statements matching their overall aesthetic.

Complementing any outfit and occasion seamlessly, an old money hairstyle is a go-to option for you. Due to its versatility, you can also style it in different ways matching any occasion. Therefore, we will first take a look at various old money hairstyles for men and women and afterward show you how to get an old money hairstyle and how to style it according to the occasion. 

Old money hairstyles male

Let’s start with the old money haircuts for men. This section will feature lots of timeless cuts suitable for any occasion that match the old money aesthetic perfectly.

Ivy League Cut

This style became popular in the 1950s and 60s in the prestigious Ivy League universities. In those old money universities like Harvard or Yale, the Ivy League cut stands for a neat and clean appearance. 

With short sides and a short back as well as a longer front part, this style is a true classic. You can style the front part to the side and get a formal but timeless aesthetic. This style is suited best for round and oval face shapes due to it elongating the face a little. 

Crew Cut

Coming from military origins, the crew cut is a minimalistic and low-maintenance hairstyle with a timeless and classic appeal. Characterized by short sides and back, as well as a gradual length on top, this haircut is perfectly fitted for rectangular, square, or oval faces.

Side Part

The side part is an old money hairstyle that can easily adapt to the occasion. For a formal one, slicked-back or styled-to-the-side hair are perfect variations whereas for a casual hangout, a messier approach is the perfect choice.

Featuring short to mid-length hair at the sides and back, as well as longer hair at the top, this style mostly works on rectangular and oval faces. For square and round faces, it might work too but is not the best alternative.


The Comb-Over is a classic and timeless hairstyle where the hair on top is combed to one side, creating a neat and polished look. It is suited for any face shape due to the mid-length and not much of a lengthening effect.

Another variation, the pompadour comb-over works perfectly for oval, round, and square faces due to the lengthening effect.

Slicked back

The slicked-back hairstyle is similar to the comb-over but in a more formal way. With lots of pomade or gel, this hairstyle suits any formal occasion very well. Also, this old money haircut is perfect if you have a rectangular face shape or a diamond or oval face. It provides width and texture.

Mid-length middle part

With mid-length hair and a timeless appeal, the classic middle part is a great old money haircut for any occasion. Even though, you will see this hairstyle a lot in recent days, the middle part is a timeless and elegant hairstyle. This cut works with any face shape.

Messy curtains

The messy curtains are a hairstyle that became popular in the 1990s and early 2000s. This, well, messier haircut with longer hair can resemble a careless old money look perfectly. Keep in mind though, that you will not want to go too messy or unwashed as it will look sloppy.

You can also go for a man bun which is a rather modern style if the occasion is more formal. The messy curtains are suited very well for square, oval, rectangular, or diamond-shaped faces.

Classic side sweep

This sleek and polished hairstyle reminds me of the stock brokers and businessmen of the 1980s and ’90s. With hair combed to the side and a short to mid-length back this haircut is both timeless and elegant. It suits formal and casual occasions perfectly and suits an oval, square, or rectangular face best. Also, it will work great with a hat.

For more inspiration on old money hats, check out my recent article here.

Classic tousled Curls

The classic tousled curls are a little shorter than the messy curtains and typically reach the chin. This style reminds me of a sailing adventure, one of old money’s most-loved activities. 

This style works well with any face shape due to it not lengthening the face or making it appear much bigger.

Curly quiff

Lastly, on the list of great old money hairstyles for men, we have the curly quaff. This timeless hairstyle works best with mid-length hair. Typically, the top hair is longer than the side and back which is not particularly short either.

This style suits any occasion perfectly and will work perfectly on an oval, round, or square face. This is the best curly old money hairstyle for men in my opinion.

Old money hairstyles female

Now, let’s make a switch and head to the old money hairstyles for women. These haircuts will most of the time fit any occasion as they will always look stylish and elegant if not messed up.

Classic chignon

The classic chignon is a great hairstyle you can achieve with many longer cuts with no pony. It perfectly fits underneath a fascinator or other old money hats and generally has an elegant vibe to it. Also, it can be worn on casual occasions due to its versatility and practical usability. 

To achieve it, gather the hair at the nape of the neck, opt for a low placement, and secure them with a pin or multiple ones. Also, you can add hair accessories and make it look voluminous. It suits every face shape as well.

Glamorous waves

This style will also work with longer hair and is a way to spice a “normal” hairstyle up. You can either apply those elegant waves on a middle or side part by curling the hair. This style is often associated with the red carpet and generally formal occasions. 

Due to it adding volume, I would wear it to a smaller face shape like an oval or rectangular face. 

French Twist

Similar to the classic chignon, the French twist offers great use for any occasion and face shape due to its versatility. You will find it at a formal diner or just at a casual hangout with friends.

To achieve this hairstyle, you will want to form a horizontal roll by twisting the hair upward along the back of the head and positioning it in the center of the back of the head. Then, secure it with pins or a comb.

Low Bun

The low bun looks similar to the classic chignon but is located lower than it and of a different structure. It typically involves simply gathering the hair at the desired position and securing it with a hair tie or pins. Therefore, it is mainly suited for casual occasions but can also look great formally if done right.


The bob hairstyle is a very versatile and modern hairstyle with low maintenance. It typically reaches to the chin at max and will suit any occasion without much styling. Typically, you will want to wear this haircut with an oval, rectangular, or diamond-shaped face. For bigger face shapes it might just be too voluminous. Either way an amazing old money hairstyle.

Short sleek hair

The longer version of a bob and pretty much the same as a Vintage Pin Curls haircut but without curls is the short sleek. This hairstyle offers an elegant version for any woman. With lots of ways to style it (try a ponytail, some hair accessories, or just classic straight hair) this style offers lots of variety. For the most formal look, opt for straitened hair and maybe a little accessory.

Vintage Pin Curls

Vintage pin curls were a modern haircut in the 1920s to 1950s due to influences like Hollywood. To style this timeless haircut, you will want to curl your hair in small sections, typically 1-2 inches wide. Let the curls sit for some time and after removing them, comb through them with a wide-tooth comb. 

If you want to, add some hairspray at the end. This style suits any face shape due to its versatility and sophisticated look.

Sleek ponytail 

This picture shows a woman wearing tennis clothes and wearing a sleek ponytail.

The sleek ponytail typically is a youthful and rather casual old money haircut. You can easily achieve this aesthetic by just ironing your hair and gathering them at a desired, optimally high, point. Then, just secure them with an elastic band or a hair tie and they are ready.

This style suits old money activities like tennis or golf perfectly and makes a great appearance under any cap. 

Find out more about the old money golf or tennis aesthetic in those articles.

Long loose curls

Long loose curls are a timeless and elegant hairstyle that can look stunning on a woman. As the name says, this style just involves long curls looking a bit messier than the glamorous waves.

It suits any face shape well and is mostly great for casual occasions. You can pair it with any outfit to achieve the old money aesthetic.

Straight long hair

This old money haircut does not have a specific name but rather it describes long hair that are not styled by any means. Besides ironing them, these hair can be styled with a hair circlet and match a variety of styles. Also, they suit any face shape very well.

How to get an old money haircut

So, with your recent research about various old money hairstyles, let’s take a look at how to get the timeless haircut you want that suits you well. Therefore, we will look at two main steps.

High-quality barber or hairdresser 

First of all, you will want to find a good barber or hairdresser. Don’t just pick a random $10-a-cut-barber at the corner but instead opt for a barber or hairdresser who understands what they are doing based on recessions and experience.

This barber or hairdresser can then help you find a great haircut for you if you are still unsure of what you want. Additionally, you will not have to run to the barber the next week because something got messed up. For my hairdresser, I am paying $28 and it is worth every penny. Women will pay more, that’s for sure.

Adapt the hairstyle to the face shape

To really nail your appearance, choosing the right haircut for your face type is crucial. Therefore, try to find out what face shape you have and then read through this article to find out which hairstyle suits your face shape best. 

Here is a video that explains in detail how to find out your face shape. In my article, I only referred to the 5 basics oval, round, square, rectangle, and diamond as those are the main ones in my opinion.

Celebrities with old money haircuts

So, with your face shape and the perfect haircut for you, let’s have a look at which celebrities rock old money haircuts.

George Clooney

The classic side part is a well-known symbol of George Clooney’s appearance, one of the greatest actors of all time. With the side part, he looks great and formal every time.

Leonardo DiCaprio

Famously known for his classic side or middle part, Leonardo di Caprio sports the old money hairstyles very well. As you might know, he looks stunning wearing those hairstyles. He also is featured in multiple old money movies.

Find out about 25 old money movies here, at least 3 of them include Leonardo di Caprio.

Julia Roberts

Talk about glamorous waves and look for inspiration. That’s when you will find Julia Roberts. The American actress rocks this old money haircut looking timeless and elegant.

Charlize Theron

Charlize Theron has had multiple haircuts in her career. Some do stand out from the others like her Bob or the French Twist she pulled off.

Old money haircuts matching outfits

Lastly, we have to talk about matching the haircut with the outfit and therefore with the occasion.

Formal cuts

For formal occasions, you will want to wear formal old money outfits and your hairstyle should ideally match the overall aesthetic. Therefore, opt for a put-together haircut without messy hair. As a man, apply some pomade or gel and as a woman, opt for a clean look.

For a general guide on formal old money outfits, check out my article here.

Casual cuts

For a casual meetup, a messier haircut is perfect. Not the haircut has to be messy but the way you style it can be a little laid-back in general. With this, you will save lots of time getting ready and won’t come off as overdressed.

Final thoughts on old money haircuts

As you can see from this article, old money hairstyles are timeless and elegant and offer versatility and a great aesthetic. Get yourself a matching haircut for your face shape and style your old money aesthetic with matching outfits.


What are the best old money haircuts for men?

The best old money haircuts for men are the Ivy-League cut, the side part, and the slicked back.

What are the best old money haircuts for women?

The best old money haircuts for women include the bob, the French twist, and the glamorous waves.

Does old money dye their hair?

Old money individuals typically do not dye their hair and if they do so, they will only opt for natural colors and no crazy variations.

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