23 best preppy outfits you need to know

Preppy outfits are mostly common in the upper-middle and upper class. Prep typically follows exact rules when it comes to its outfits and ways of styling.

Therefore, let’s dive into a list of 23 of the best preppy outfits for men and women.

Preppy aesthetic

The preppy aesthetic consists of the offspring of wealthy families. They follow traditional rules to live their life by. Unlike the old money aesthetic though, prep likes to sometimes break these norms and be more outgoing and crazier. May it be getting drunk at an exclusive party or breaking with the standards of clothing, prep likes to stick out. 

Creating unique outfits is something, prep likes to do, combining traditional clothing with sporty or outstanding items that will match.

Preppy outfits

This list will contain some outfits, you can put together with preppy clothing, to match the preppy style. The list will be divided into preppy outfits for men and women.

Preppy outfits for women

Unlike preppy outfits for men, the outfits women wear are more based on the typical beauty ideal of the 1960s and 70s. Even though most of the outfits are combined, just like the male ones, they are different in detail. 

Mini skirt & Blazer

The combination of a mini skirt with a blazer is a typical preppy outfit. Perfectly suited for the warm months this can be a great option. Depending on the length of the skirt this can even be worn on business occasions.

Try to keep it simple with the colors as you don’t want to mix them up too much. The outfit can be combined with preppy shoes like boots. 

Check/Tartan dress

Ideally suited for either formal occasions or a casual walk on the golf course. The dress with check or tartan patterns will be suited for warmer months. Keep in mind that the fabric can be warm. Don’t wear this dress during a heat wave or extremely high temperatures. Try to wear a lighter fabric for the hottest days.

Some heels fit this outfit perfectly as well as some jewelry. 

Nantucket red shorts & Button-down shirt

For a unique outfit combine some Nantucket red shorts with a button-down shirt. Though this outfit can be very colorful, try to keep the colors matching. Otherwise, you will look sloppy. Try to opt for quality or else, the outfit will lose lots of the vibe. 

The outfit can be worn on formal occasions. Moreover, this combination can be expanded to be even more formal, with a blazer.

Pleated skirt & Mary Janes & Cardigan

For this preppy outfit, it is crucial to decide on a color scheme. Try to keep it light, dark, or based on a series of similar colors. Typically, the Mary Janes are black or dark blue. Even though this outfit can be worn in the warmer months, I wouldn’t recommend wearing it in the heat. Rather than wearing it in the warmer months, try to put on some tights. To keep you warm, you can layer the cardigan with a shirt or something else to ensure a little more of an edgy style.

Sailing outfit

Another outfit that is made for cold weather is a sailing outfit. This outfit is not only meant to keep you warm. Moreover, it should be suited to withstand heavy winds and splashing water while still providing enough space to maneuver properly. Therefore, layering can be a great option. To keep you warm, sweaters are a great option. 

Try to opt for either cable knit sweaters or V-neck sweaters. These will offer enough room for an oxford shirt to withstand the wind. 

School uniform

Prep likes colleges universities and especially Ivy League universities are something desirable for them. As a result, school uniforms are pretty commonly worn by prep. Though real school uniforms are even better, you can surely recreate one, using the right clothes. 

School uniforms are commonly based on one color and the outfit is built around that. Skirts are a usual thing as well as blazers or sweaters paired with a button-down shirt. 

To check out more preppy school outfits, read my recent article here.

Tucket sweater over the shoulders

Something that also works for the old money style, as well as the preppy aesthetic is a tucked sweater over the shoulders. This not only looks stylish but even more offers a great opportunity to carry something with you when it gets colder. Especially in the early summer when it pounding hot in the sun but rather cold in the evening, a tucked sweater over the shoulders is a great option. 

In this particular outfit, it can be paired with a mini skirt as well as a button-down shirt.

Bias check dress

Perfectly suited for formal occasions, a dress with bias check patterns is a great piece of clothing. Additional to this dress, a button-down shirt can be worn underneath to create a school uniform-like look. 

This outfit can be combined preferably with heels, but some sneakers are also an option. For some more formal outfits, check out my article about preppy workwear here.

Plaid skirt & sweater vest

Suited for the colder months, a mid-length skirt with plaid fabric and a sweater vest is a great preppy outfit to wear on formal occasions.

Paired with some boots and a button-down shirt, this outfit can get pretty colorful. Try to keep it simple though! If you mix too many bright colors, this outfit will not be suited for formal occasions anymore and will look overdone. 

Chino pants & Cable knit sweater

This outfit is one of the few that can be colorful. As seen in the picture, this outfit consists of a pair of Chinos and a cable knit sweater as well as some Loafers. This outfit should be primarily worn on casual occasions as it can be too bright for formal ones. 

For this fit, you can create unique looks and be experimental with colors, as there isn’t much you can do wrong. 

Shorts & Striped Top

To match the former sailing look for the warmer months, shorts and a striped shirt can be worn. Beyond, this outfit can be added up with a nice blazer to create a more business-like look. Even though this look will be created, I would still recommend wearing it primarily for casual occasions. 

Dominating colors should be blue and white or beige. For more nautical preppy inspiration, check out my recent article here.

Polo shirt & Dress pants

To combine sporty clothing with something formal, a polo shirt combined with dress pants is a suited outfit. Unlike other preppy outfits, where it is mandatory to combine colors, this outfit can mainly consist of one color. 

A belt is something that creates some contrast, to not make it look like a pajama. Nevertheless, this outfit can also be worn on formal or casual occasions.

Preppy outfits for men

After a long list of outfits for women, we finally come to the male section. The outfits will consist of a combination of casual or sporty and formal attire to create a contrast between old, traditional clothing and the new, trendy style. If you want to learn more about it in detail, read my article about the preppy style for men.

Shorts & V-Neck sweater

This outfit is the perfect example of a combination of formal attire paired with some sporty clothing. To even underline this fact further, in this picture the man is equipped with a tennis racket. The sweater and the shorts should create a contrast, through color, texture, or both. Additionally, preppy shoes, like white tennis sneakers, add up to this outfit perfectly. Additionally, you can wear a button-down shirt underneath the sweater for a more formal look.

For more sporty preppy outfits, check out my recent article here.

School uniform look

Just like the female version, this outfit consists either of a school uniform or clothes that will imitate one. Crucial for this outfit is formal attire, like a suit jacket and dress shoes or Loafers. Furthermore, this outfit should be combined with a button-down shirt and most of the time a necktie with the school’s typical colors. In addition, a formal pair of trousers, like chinos or dress pants suits this outfit very well.

Casual preppy outfit 

This casual preppy outfit combines formal attire with casual clothes. Moreover, the striped polo shirt combined with the Loafers and dress socks creates a unique look. Furthermore, this outfit consists of a combination of accessories, like a watch, sunglasses, or bracelet. For trousers, you can choose anything that matches your aesthetic.

Outdoor outfit

A preppy outfit suited for the colder months is this one. Starting with the shoes, this outfit can’t be any more preppy. The JJ. Bean boots are not only the perfect footwear for colder seasons and outdoor activities but also look great. Moreover, the zip hoodie adds a relaxed vibe and can be used for layering. Some gloves, like those portrayed in this picture, can be added but are not essential.

To get more inspiration on what to wear in colder months, check out my article about 13 preppy winter outfits.

Sporty summer outfit

If you are playing sports games at a party in the summer with your well-off friends, this outfit will suit the occasion perfectly. For this occasion, a nice button-down shirt is as crucial as a belt. Furthermore, the pants can be chino pants or shorts. A detail that mustn’t be overlooked is the footwear. Loafers or boat shoes add up to the occasion perfectly.

Cocktail party outfit

Are you invited to a cocktail party and don’t know what to wear? This outfit is exactly suited for you. Even though this picture portrays a party with a sailing theme, the outfits still work fine at any place for a cocktail party. Starting at the top, a button-down shirt is crucial, the fabric can be chosen. Blazers can be worn but are no must-have. Additionally, the trousers should be chinos or other formal pants. For shoes, Loafers or boat shoes will do a great job.

Formal boat outfit

If you want to seal the deal on a boat with some clients or business partners, this outfit will be perfect. The combination of a button-down shirt with a unicolored sweater and a great pair of chinos not only withstands the winds of the sea but also looks very formal and preppy at the same time. You should create contrast in colors as otherwise, this outfit will not look as formal.

Relaxed sports outfit

This preppy outfit creates a very relaxed look. Even though this outfit is considered preppy I wouldn’t recommend wearing this to anything else than a casual occasion where you go shopping or to the gym, or to play sports. The combination of sweat shorts and a sweater creates a chill look that is nevertheless somewhat suitable to go out in public.

Colorful look

This outfit is suited to go on an adventure with your friends or to just hang around. Typically, this outfit consists of button-down shirts with unique patterns like elephants or palm trees and monkeys combined with some colorful pants. Additionally, Loafers are a great shoe to wear to that outfit. 

School uniform casual outfit

Unlike the previous outfit, this one is suited for casual occasions. This zip sweater with university logos can be combined with anything that is considered prep. If you want to dress it up, wear matching button-down shirts and a necktie. If you want to dress it down though, you can go for a polo shirt or a simple white t-shirt.

Matching colors summer outfit

If you have the confidence to wear it, a matching color outfit can be the real deal for a casual occasion. Perfectly suited for a barbecue party with your well-off friends, the matching colors will make you stand out. As a result, you can do this, as portrayed in the picture, by combining a striped polo shirt with matching pink shorts or with some linen fabric. 

Nevertheless, I would recommend not wearing this outfit daily and just having it as an addition for a fun occasion.

Final thought on preppy outfits

As portrayed in this article, the preppy style consists of many preppy outfits that will make you look great and suit any occasion. To wear this look right, try to opt for quality over quantity when it comes to your clothing. Nevertheless, these preppy outfits will create a unique look.