The Preppy Style: 7 features you must know

Two men are standing on a wooden boat at a lake. This image represents the preppy style.

The preppy style is commonly associated with the offspring of rich, old-money families that likes to dress a certain way. This article will cover in detail what this style is all about and how you can implement it in your daily outfits.

Along with a detailed description of different core features, the history and modern appeal of this timeless style will be discussed. Also, you will get some inspiration how to wear it on your own in the end.

If you went to check out how preppy style looks in much more detail for each gender, check out my article about preppy style for men and the preppy style for women.

Definition of the preppy style

Preppy style refers to a fashion trend that originated among students at Ivy League schools in the Northeast of the United States during the 1950s. The at first low resonance rose pretty high up with the polished book “The Preppy Handbook” by Lisa Steinbach. Though meant as a joke, many preps still follow the rules of this book to live a preppy life.

The term “preppy” derives from the word “preparatory,” as these schools were mostly attended by students preparing for prestigious Ivy League universities. Therefore, it is no wonder that you can encounter many students wearing preppy outfits.

If you want to learn more about preppy outfits for men and women and get some inspiration, check out my other article.

Preppy style in modern time

Nowadays, the preppy style combines the different periods and offers a combination of the more conservative style and the relaxed one of the 1990s. 

With contemporary preppy fashion incorporating elements of streetwear and modern fashion trends, the preppy style manages to stick out once again besides all the others. However, the core values of classic, high-quality clothing and a focus on tradition remain central to the preppy aesthetic. 

Trademarks of the preppy style

Now, let’s look at some key characteristics. The preppy style is characterized by clean, classic lines, unique patterns, and a focus on traditional, high-quality clothing.

1. Unique button-downs

One crucial component of preppy style for men and women is the use of button-down shirts. Whether it is in form of a classic dress shirt or an Oxford shirt, button-downs will always level up a preppy outfit.

Optimally, you will want to opt for two to three ones in neutral colors like grey, light blue, or white.

2. Timeless tops and shirts

Additionally, timeless tops and shirts offer a great way to express a casual preppy vibe. Therefore, polo shirts, rugby, shirts, and classic tops are great garments. Opt for mostly neutral colors but also make sure to add some bolder ones. Pink, yellow, green, and red are great colors when it comes to this style.

3. Elegant sweaters

To either layer or wear them on their own, elegant sweaters offer a great and versatile use in terms of preppy style. With the collared option or a simple cable-knit sweater you can do nothing wrong.

Also, you may opt to check out my article about old money sweaters to gain additional inspiration.

This picture shows a sweater looking just like the one from Tommy featuring old money great.

4. Pleated skirts

Pleated skirts are core essentials of the preppy style. May it be with a gingham or checkered pattern or a plain alternative, they represent the preppy style perfectly. Also, women can opt for the sporty alternative, the tennis skirt. This one typically comes in white whereas others mostly feature other neutral colors like navy or grey.

5. Elegant chinos

Chinos are core essentials of the preppy style for both men and women. You will find them in almost any timeless and sophisticated outfit. Due to their use for casual and formal occasions, chinos and khaki pants in neutral colors offer a great option for any outfit.

6. Unique shoes

Unique and timeless shoes will complement any outfit of prep perfectly. To find the right ones, here is a list of shoes:

  • Loafers
  • Boat shoes
  • Mary Janes
  • Ballet Flats
  • Elegant sneakers
  • Pumps
  • Boots

Here, you will want to opt for high-quality natural materials to ensure a timeless and enduring appeal. Get a more detailed guide on preppy shoes here.

7. Luxurious accessories

The Last feature of the preppy style is it’s timeless and sophisticated accessories. Ranging from fine jewelry to belts, sunglasses, and scarfs, you will find numerous ways to complement your outfits accordingly.

To find out more, check out my recent article about preppy accessories here.

How to incorporate preppy style in your everyday outfits

If you want to try out the preppy style yourself but don’t want to go on full send, this paragraph is perfectly suited for you:

In order to look preppy, you have to first follow some basic principles. One of them is to try to match your clothing. Also, you should combine something sporty and casual with formal items of clothing. If you are following these rules, you will have no trouble looking put-together and preppy. 

If you are wearing a pair of jeans, try to go for a plaid button-down shirt and a blazer. Depending on the weather you can either opt for some fashionable white or black sneakers or Loafers. 

When it’s summer and it’s getting warmer outside, some linen button-down shirts or linen trousers are a great option. Paired with some Loafers or boat shoes, this will look amazing. You should opt to wear light colors such as beige, khaki, or white.  

If you are going out for a meeting with your friends or family on a summer day, try to wear a colorful but matching polo shirt. You can combine this with some chino pants or shorts to make this look even better. Additionally, if you are a woman, a blouse and a skirt should be in your wardrobe. 

With these items, you can level up your daily style and start looking more preppy as you progress.

Final thoughts on the preppy style

As a result of over 70 years of evolution, the preppy style is one of a kind. Typically expressed by button-down shirts and chino pants as well as blazers and Loafers, this style will make you look unique. 

You can add it to your daily outfits or stand out as a style on its own, depending on your budget and occasion. Nevertheless, the preppy style is something you should consider wearing to any occasion as it will suit them perfectly. 

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