Cultivate your style with these preppy shoes

Preppy shoes are an essential item to complete your preppy aesthetic. They not only contribute very well to preppy outfits overall but can even set the tone depending on the occasion.

General Requirements to preppy shoes

There are different preppy shoes worn depending on the occasion. In general, they have to suit the preppy style and match the outfit, just like any regular shoe, which they are. Since prep typically comes from the upper-middle-and upper class, these shoes also serve the purpose of being suitable for the office or spontaneous meetings with either the business partners of the parents or their business partners.

Thus, preppy shoes serve different purposes, one trait of them is their cleanliness. No one likes to wear dirty clothes full of sprinkles of mud and sand from the tennis or golf court, so they should always be cleaned, especially if they are white. Speaking of colors: Preppy shoes are usually in certain colors to fit the preppy clothes they are worn with. These colors are mostly white, blue, brown, and black.

Let’s look at them always to ensure you have a fitting pair of shoes for any occasion.

Preppy shoes

This list will not be divided into male or female, as some shoes fit each gender. Keep in mind that only because it is a particular type of shoe, not every style can be worn to match the preppy aesthetic.

Loafers

The ultimate footwear of prep, regardless of gender, is Loafers. The cropped shoe is the perfect footwear for any casual or business occasion and fits almost any outfit in the warmer months. Typically made out of leather these shoes will cost you some money but their quality is very good and they will last you a long time.

The shoe is meant to add to the outfit smoothly but not dominate by standing out. To keep it in the background, try to wear subtle colors like blue, grey, beige, brown, navy, and black. Shining colors and bright red doesn’t suit the preppy style when it comes to Loafers.

Polo Ralph Lauren crafts fine loafers, yet brands such as Gucci excel in producing premium ones too. Don’t be shocked by rather high prices as they will serve you a long time.

One trait that defines them is their missing laces. They all hold to your foot just by their shape and design. Also try penny loafers as they have a little decor on the tip of the shoe. Loafers that are equipped with laces are called boat shoes. These are typically worn on a boat and can be quite difficult to differentiate from the traditional ones.

For boat shoes, there are the same rules as for Loafers when it comes to colors. Whilst they can get wet though, loafers should be dry at most times.

They are also made out of leather and have non-marking rubber soles so that they can be worn on the deck. Some boat shoes are made out of canvas for more comfort.

Here, you can see a woman wearing some white Loafers. They are made out of leather with a brown sole. — White leather loafers

Marry Janes

Mary Janes or doll shoes are shoes that have a rounded toe box and a strap fastened with a button to open and close them. They are uniquely worn by women and for casual or business occasions. You might combine these stylish preppy shoes with somewhat of a school uniform.

Made out of leather, these shoes are not only pretty expensive and also don’t look that comfortable. With these, you will point a lot of attention to your feet for sure.

Whilst Mary Janes were typically meant to be doll shoes, over many years they evolved into pretty fashionable footwear as now there are many shoes considered Mary Janes that look quite good on many outfits. Now they come with big heels and even plateaus and in many colors.

Maybe try to pair the with jeans to create a new look.

Here, you can see a woman wearing Marry Janes, some preppy shoes. — Marry Janes

Sandals

Though there are many different types of sandals, only a few of them are considered to be preppy shoes. They are worn by women when it comes to the preppy aesthetic. Men refrain from wearing sandals in this style. To get to know more about them, check out my article about preppy style for men.

Typical types of sandals women wear are ones with thong (also called casual) or clog sandals and boating jacks. These can be pretty fancy and don’t have to be restrained at all. Nevertheless, they should be picked with a good sense of fashion. Don’t buy a cheap imitation of some trendy ones just to look like you got money.

They should have a leather sole as well as a colorful strap. This can be either golden or white or black. Unlike Loafers, sandals can stand out a bit as they are usually worn with shorter clothes and can lengthen the legs.

High-quality brands are Jack Rogers and Tods. Definitely try to get yourself a pair of jack rogers sandals!

In this picture, you can see a woman wearing some preppy sandals with leather straps. — Preppy sandals

Rain boots

In case prep goes hunting or does some activity that requires being in the mud, it surely wants to look good doing it. Hence, stylish rain boots are a must for achieving the preppy look. Of course, these shoes shouldn’t be worn on a casual or business occasion but for outside activities, boots and especially rain boots are a great option.

The material should be rubber and the colors can be anything from black to white except shining ones. Especially Hunter rain boots are a great option when it comes to preppy shoes as they are perfectly suited for any muddy occasion and make you look great wearing them. I would recommend owning one single pair of them though as the occasion will not come as often.

Boots

From rain boots, we now come to regular ones. Similar to rain boots, both can be worn by men and women. Nevertheless, there are major differences.

You can not only tell by the color but also the shape or height, which boot fits each gender. The boots women wear as the preppy style, are usually with taller heels and reach high up, almost to the knee sometimes.

Preppy boots are typically held in a dark or light brown or dark blue. Just like Loafers, they are typically made out of leather or suede to match that preppy fall aesthetic.

For some more inspiration on preppy outfits for fall, check out my article here.

Men in the preppy style don’t frequently opt for boots, but they still embrace them. They typically wear bean boots. These ones may look a little out of fashion but are mostly worn to walk in nature, not on the streets. The colors are, just like the boots for women, light and dark brown or even black.

While women can gracefully wear preppy boots to formal and casual events, men should mostly avoid them in formal settings. Nevertheless, they still may wear them with some formal preppy outfits, just not a tie or something similar.

In this picture you can see a man wearing bean boots with yellow laces. — Bean Boots

White tennis shoes

Prep likes to participate in exclusive hobbies. One of them is tennis. For obvious reasons, prep likes to wear tennis shoes. Not only are these shoes mandatory to even play tennis but also, they can make up pretty decent outfits.

No matter the gender, tennis sneakers will most likely complement your outfit. One important factor though is the color of these sneakers. Tennis sneakers should be white. Even though this can be a pain to clean them, it will be worth it.

If you keep care, you just need to buy a new one every year due to extensive usage. Generally, white sneakers make an excellent choice for preppy footwear.

You can see this woman wearing some low-cut preppy tennis shoes. She seems to keep them pretty white. — Low-cut tennis shoes

Ballet flats

Looking almost like Loafers, but with a more wide-cut opening at the metatarsus, ballet flats are preppy shoes that can match an outfit perfectly. Worn by women only, this is the go to shoe for formal occasions or a casual one in the summer.

The right pair should be high quality and in discreet colors. The shoe can also be striped or two-colored in general, like a beige shoe with a black tip. Just opt for a great feel as you will wear them throughout your entire day.

Dress shoes

Dress shoes are not only the perfect footwear for formal occasions in general but especially when it comes to the preppy aesthetic. Both men and women can and should own one pair of dress shoes at least.

Preferably these shoes are made out of leather and black or brown. Depending on your preferences they can be mat or glossy. Opt for a sleek option!

This man wears some preppy dress shoes consisting of brown leather and matching laces. — Brown dress shoes

Summary

As you can see, there is a preppy shoe for almost any occasion. The key factor of these shoes is quality. No matter how they look, quality should always be the number one priority. Your favorite preppy shoe may also be a great conversation starter.

Besides that, try to keep the shoes clean to not look scruffy. If you want to build your preppy wardrobe, I would recommend to pull one pair of Loafers, a pair of white shoes, and a pair of black dress shoes. These can be worn with most preppy outfits.