26+ Must-have Preppy Capsule Wardrobe Essentials For Your Daily Preppy Outfits

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Preppy Capsule Wardrobe Essentials For Your Daily Preppy Outfits

Wanna wear preppy outfits effortlessly? All you need to do is have a preppy capsule wardrobe and be creative with the preppy wardrobe essentials!

In this post, I will show you what you really need in your preppy capsule wardrobe. Plus, some useful fashion tips related to the preppy aesthetic.

Alright, let’s check them out!

Preppy Capsule Wardrobe Essentials

Preppy Clothes


Shirts are literally the basics of preppy style. They are often layered with sweaters, cardigans, and blazers. Shirts made of Oxford cloth are not only great for preppy outfits but also excellent items to invest in. They are very durable, which means you can wear them for a long time, and suitable for both casual and formal occasions. In addition to common button-up shirts, button-down shirts (the shirts that have buttons on the edges of the collar) are also something you can consider wearing.

Solid shirts are classic and versatile, while striped shirts can add flavor to your preppy looks. I would say the colors of white, soft blue, and soft pink are classier and highly recommended. (Especially for spring and summer) If you choose a darker color like navy, it is likely to give a mature and sophisticated image.


Polo Shirt

Polo shirts are widely worn by athletes, especially polo players, tennis players, golfers, etc. Preppies enjoy those sports, so polo shirts are undoubtedly one of the preppy wardrobe essentials.

Polo shirts are less formal than shirts and can be more comfortable compared with some types of shirts because of their softness. In other words, they are good to wear daily! Pairing polo shirts with solid pants can be natty while pairing them with mini skirts can make you look really lovely.


Rugby stripe polo shirts are also something that frequently appears in preppy outfits. Because of their bright colors and stripes, you can effortlessly create a dynamic, casual, and sporty preppy look with these polo shirts.



Only wearing a shirt or pairing it with a blazer can sometimes look very professional, and therefore, unapproachable. Simply putting on a sweater can add a touch of gentleness, warmness, and coziness to your outfit! The easiest and most typical way to dress like a preppy is to wear a sweater on top of a shirt, or wear a shirt and then put a sweater on your shoulders and tie it up. (Some of you may already know this is one of the most iconic preppy looks!)

Here are some sweaters that can help you achieve the preppy look:

  • V-Neck Sweater: This is nice to highlight your necktie and bow tie. I like the one with contrasting stripes at the edge, which looks very fashionable.
  • Cable Knit Sweater & Fisherman Sweater: A sweater with a texture can make your outfit less boring and cuter!
  • Turtleneck Sweater: This one seems less common in preppy style, but you can still have a classy preppy look with this. For instance, you will look great when you pair a turtleneck sweater with a blazer or a V-neck sweater (with contrasting stripes!). Plus, it’s good to wear on a cold and windy day.

It’s better to have a solid sweater in your preppy capsule wardrobe because it can match all the other preppy wardrobe essentials. Also, it contrasts with a plaid mini skirt (which I will talk about later), and they form a decent preppy outfit (many school uniforms consist of solid sweaters and plaid mini skirts).

However, if you want to try something different, it’s totally fine! You can do the opposite, like pairing a plaid sweater with a solid mini skirt. Moreover, you can wear a striped sweater or a graphic sweater to make your preppy outfits more appealing!


Sweater Vest or Suit Vest

In addition to the sweaters I mentioned above, you have another option which is the sweater vests! They are perfect to wear in spring, on a cool summer night, and at the beginning of the fall. I particularly like the combination of a sweater vest and a striped shirt. The sleeveless design of the vest makes the stripes to be more visible. It is quite refreshing and stylish.


Suit vests are fun items to flavor your preppy outfits. They can be dressed for formal occasions or worn casually for a more relaxed look. Suit vests can be cute and stylish, depending on how you style them. Typically, suit vests are paired with blazers. Whether you choose a matching or contrasting suit vest for your blazer, either way, can elevate your chicness to a higher level! Of course, you can experiment with other items for a different look if you feel like it.



Cardigans can be an alternative to sweaters. That means you can wear a cardigan exactly like a sweater. But I would like to let you know some benefits of wearing a cardigan: You can wear it as a light jacket and take it off whenever you want to. And you can easily change the look by buttoning all, unbuttoning all, or buttoning some of the buttons. Depending on the design of a cardigan, the buttons can be an accent. If you wear a contrast trim cardigan, you can certainly grab some attention!


Mini Skirt

Without a preppy style mini skirt, your preppy capsule wardrobe will never be completed. That’s how important it is. The mini skirts I recommend the most are pleated mini skirts and plaid mini skirts. Think about uniform skirts and tennis skirts, and you may understand why I recommend those skirts for your preppy outfits. You can also consider wearing a pencil skirt for a more sophisticated look. If you’re tired of thinking, that’s ok! Any of the skirts below can help you create an attractive preppy outfit!

SolidSolid Pencil Mini SkirtSolid Pleated Mini Skirt
PlaidPlaid Pencil Mini SkirtPlaid Pleated Mini Skirt

All of them are really cute, but I want to briefly mention the white pleated skirt. It is a great item to wear in summer because it makes you feel cool visually.


Shorts or Bermuda Shorts

When you get tired of wearing mini skirts for your preppy outfit, try upgrading it with dressy shorts and Bermuda shorts (a type of shorts whose length is slightly above the knees) for a fresh look! Even if you wear shorts, you can still look classy and sophisticated by pairing them with shirts, polo shirts, sweaters, cardigans, etc.

Those shorts are not only preppies’ summer outfit essentials but also one of the best items to wear when they go yachting or on vacation. It might be fun to try a preppy summer look with these shorts when you go on vacation, just like the real preppies!



Preppies always have at least a pair of dressy pants that can be worn on formal and casual occasions. (How convenient!) These tips may help you find the perfect preppy style pants:

  • Consider adding a pair of slacks, chinos, or cropped pants to your preppy capsule wardrobe.
  • Whether you choose slim-fit or straight-fit pants, both are great! Slim-fit pants can give you an edgy look, while straight-fit pants can make you look charismatic.
  • As for colors, choose the colors that never go out of style, such as white, beige, khaki, gray, navy, black, etc.
  • The pants (and shorts) without any pattern are preferred for a timeless look. But if you want to have fun with your fashion occasionally, having an extra pair of patterned pants (or shorts) is not a bad idea!


Wearing one of these dresses can let you effortlessly embody the preppy aesthetic:

  • Shirt Dress: It can be solid or striped. Some are belted and some are not. If your shirt dress is not belted, you can occasionally add your own belt to give it a different look.
  • Polo Dress: Remember the polo shirt I mentioned earlier? A polo dress is like the longer version of a polo shirt (just like a shirt dress is a longer version of a shirt). I think it is super cute!
  • Striped Dress: A casual striped dress that has nautical vibes is a great one!
  • Collared Dress and Tie Neck Dress: These dresses can remind us of shirts and bow ties (The preppy wardrobe essentials). Not all collared dresses and tie-neck dresses are suitable for preppy outfits, but some can help you achieve a lovely preppy look.
  • Shift Dress: Jacqueline Kennedy Onassis, who was considered one of the most influential fashion icons and the icon of preppy style, often wore various shift dresses. The minimal and elegant design is probably why the preppies love shift dresses. Besides the timeless solid shift dresses, bright printed shift dresses, especially the ones from Lilly Pulitzer (a famous fashion brand that associates with preppy style), are adored by the preppies as well. Those shift dresses are ideal for wearing on weekends, vacations, and social occasions. (These activities are important to the preppies.) In fact, Jacqueline Kennedy Onassis wore Lilly Pulitzer‘s printed shift dresses and that actually popularized the brand.

Only wearing a dress may not be “preppy” enough. To make your outfit more “preppy”, try putting a sweater (whose color or pattern contrasts with the dress) on your shoulders and tying up the sleeves, just like the iconic preppy look I mentioned before. (I suggest doing it once in a while when wearing a polo dress or shift dress!)

If you just want to choose one dress to be in your preppy capsule wardrobe, I encourage you to go for a shift dress. Because if you already have a shirt, polo shirt, something striped, and a bow tie in your preppy capsule wardrobe, then I think you don’t have to be rushed to have a shirt dress, polo dress, striped dress, collared dress, and tie neck dress.


Wearing blazers that resemble school uniforms can let people easily recognize you’re wearing a preppy style. For example, a blazer with an academic logo or a monogram on the chest. Or a contrast trim blazer (the blazer that has the contrasting line at the edge).

Besides the basic solid blazers like navy (the most classic color!), dark green, burgundy, brown, gray, or black, you can try blazers with vertical stripes or plaid patterns for a fancier preppy look.


If you think buying a blazer with a logo on the chest is over your budget, here is a tip for you: You can get a blazer and a patch and attach it by yourself. It might save you some cash! But always follow the correct instructions and be careful. I hope everything goes smoothly when you do it!

Although the blazers I mentioned above are preferable, you don’t necessarily have to wear them. A blazer without a logo is still enough to complement your preppy outfits.

Jacket or Coat

A blazer is not enough for preppies to spend the winter. We need jackets and coats, especially for your preppy winter outfits! A basic wool coat (whether short or long) and a trench coat are usually the preppies’ go-to choices. The jackets and coats below are not preppy wardrobe essentials (in my opinion) but can be added to your preppy capsule wardrobe if you want to have a different look:

  • Tennis Jacket (for a sporty look)
  • Field Jacket or Waxed Jacket (for an outdoor look)
  • Peacoat (This can be an alternative to blazers)
  • Duffel Coat (This is so cute!)

Preppy Accessories


Wearing a headband can keep your hair neat and beautiful. (I think that’s what prep school wants you to be, haha) Perhaps that’s why it gives an impression of a “good girl” and is associated with “preppy”. Additionally, a preppy look with a headband is widely popularized by Blair Waldorf in Gossip Girl.

For choosing a nice headband for your preppy look, I want to give you a few tips:

  • Wear a wide headband rather than a thin one. (Come on, don’t be shy! It is fashionable and will be easier for people to recognize your preppy look.)
  • I personally don’t recommend a headband with embellishments like knots, pearls, rhinestones, etc. I think that’s too much for the preppy style. The only thing I can accept is the headbands with “understated” bows. However, if you want to wear fancy headbands like Blair Waldorf in Gossip Girl, that’s your choice!
  • Instead, try to wear headbands with different fabrics: plaid, velvet, satin, tweed, corduroy, and more! It can be a lot of fun!


Hats are functionally and fashionably useful for preppies. There is no specific hat that you have to have in your preppy capsule wardrobe because preppies wear a variety of hats depending on different occasions, such as berets, fedoras, straw hats, sun hats, baseball caps, etc. If I had to pick one to start with, I would choose the baseball cap. It is the most practical hat that you can wear every day!



Preppies enjoy various outdoor activities such as polo, tennis, golf, yachting, etc. Therefore, sunglasses are definitely a must-have! The types of sunglasses vary from person to person. The classic ones are always the safest choice!


Necktie or Bow Tie

Neckties and bow ties are parts of prep school uniforms. In some schools, neckties are for male students, and bow ties are for female students. But in the unpredictable fashion world, everything is possible! (Plus, female students wear neckties too in many schools) So, you can wear both of them for your preppy outfits!

Striped neckties are very common in prep school uniforms. Have you seen the movie Dead Poets Society? It is about the story of a teacher and students in a preparatory school. If you look closely at the students’ uniforms, you will realize they wore striped neckties! Striped neckties can make preppy outfits not so tedious compared to solid neckties. You can also choose other types of neckties, like plaid neckties, silky neckties, or neckties with special patterns, depending on your entire preppy look!


If you want to look more charismatic, I suggest wearing a necktie. If you want to look girlier, then go for a bow tie!



Adding a colorful printed silk scarf really can enrich your preppy outfit. Sometimes, it’s nice to replace your necktie and bow tie with a silk scarf for a chic, luxurious, and elegant look.


Use a plain cashmere scarf or plaid scarf to keep you warm and fashionable in fall and winter! I love the combination of a blazer and scarf, especially when the colors or patterns contrast each other.


Classic Watch

Wearing a classic watch shows what type of person you are. Maybe you value something traditional. Maybe you have taste in fashion. Or maybe the watch represents your wealth and social status… Sounds like a preppy, isn’t it?



Gloves are one of the equipment for the sports that preppies enjoy: polo, equestrianism, and golf. Since preppy fashion is mostly connected with their lifestyle, it is no wonder that gloves are one of the essential accessories that complete the preppy style.

However, you don’t necessarily have to wear the same sporty gloves as them. Instead, think about the gloves that you can wear daily. I would choose a pair of high-quality leather gloves. Not only because they can keep my hands warm on a cold day but also because they are posh and sophisticated, therefore more suitable for regular preppy outfits than sporty gloves.



Some prep schools require students to tuck in their shirts and wear the belts. This can help students to have a neat look. That is very important to preppies and a small detail that sets the preppy style apart from others. I’m not saying you must wear belts for all your preppy outfits. What I want to say is it’s good to have a belt in your preppy capsule wardrobe and use it whenever you need it.



There are three types of jewelry I want to talk about:

  • Pearl Jewelry: As you may noticed, preppies’ wardrobes are full of classic things, including blazers, silk scarves, watches, and pearl jewelry. Just like other preppy wardrobe essentials, pearl jewelry is one of the items that effortlessly makes preppies stay classy. And it will definitely make your preppy outfits much classier too! Pearl necklaces and earrings are great to start with. You can pair a pearl necklace with a shirt or a shift dress (Jacqueline Kennedy Onassis did it sometimes. She was a pearl jewelry lover!). Pearl stud earrings and basic pearl drop earrings are wonderful items to elevate your daily look. Of course, you can wear a pearl necklace and earrings as a set for the most refined look.
  • Understated Gold or Silver Jewelry: Understated jewelry like dainty pendant necklaces and minimal bracelets, which you may already have in your jewelry box, will complement your preppy outfits better than statement jewelry. (Gold and silver jewelry are basics that can match most of your looks. If you want to wear rose gold jewelry, that’s fine too!)
  • Jewelry with Nautical Elements: Some preppy outfits are inspired by nautical elements because preppies enjoy the activities on the boats. (yachting, sailing, etc.) Jewelry with nautical elements (such as anchor, rudder, and sailboat) is not a must-have but I think it is a good idea to wear them once in a while, especially in summer or on a vacation. Why not let those cute jewelry brighten up your mood?
Where to Buy Pearl Jewelry Online?


You may need different bags for different preppy looks. A versatile leather bag usually works for most preppy outfits. I highly recommend the brown color because it is posh and can match well with light-tone and dark-tone outfits. A cute satchel bag can emphasize your academic (school girl) preppy outfit and make it lovelier. When you want to dress more casually or are ready for a vacation, a tote bag or duffel bag is an ideal option.


Socks, Knee-high Socks, or Tights

Socks are so important for academic and sporty preppy outfits. Generally, socks and knee-high socks are required as school and sports team uniforms for dressing appropriately in school and protecting the athletes’ bodies when they play sports.

Socks are pretty basic and often needed for a variety of outfits, so we should have them in our preppy capsule wardrobe (you probably already have them). You can wear knee-high socks for an outstanding academic preppy look. (Especially when you wear a mini skirt!) Tights are not essentials, but you can use them to diversify your preppy outfits.

Black and white socks are always recommended. Sometimes, it can be fun to wear colorful or patterned (striped, argyle, polka dot, etc.) socks as an accent!


Dress Shoes

Dress shoes are necessary for preppies to wear with uniforms and at social events. (They can be worn with casual outfits too) What I list below is perfect to wear with your school girl preppy look. (No need to have them all. Just pick one pair that you like!)

  • Loafers
  • Oxford Shoes or Derby Shoes
  • Mary Jane Shoes and Ballet Flats (for a girly look)

Black is the color you will never go wrong. (It goes well with both black and white socks) Alternatively, you can choose dress shoes with brown, beige, and cream colors to match light-tone outfits.


Boat Shoes

The world’s first boat shoes from Sperry (also known as Top-Siders) were meant to be worn on boats. Their special design helps the wearer prevent slipping on a boat. So they are adored by those who often spend time on boats, including the preppies! After the famous The Official Preppy Handbook came out in 1980, boat shoes are regarded as the preppy style staple. (You can even see a boat shoe on the cover of the book.)

The leather boat shoes kind of have a dressy look, so they can be worn with semi-formal and casual outfits without seeming overly casual. (They are no longer shoes that are only worn on boats!) They are usually worn without socks, but it’s your choice to wear them with or without socks.



How can a preppy plays tennis, golf, or other sports without a pair of nice sneakers? Although you don’t have to play those sports like the preppies, you can be inspired by their sporty fashion!

If you want to save some money, the only sneakers you need in your preppy capsule wardrobe are a pair of white sneakers. They not only can accomplish your sporty look but also can match your academic look and a casual daily look, especially when your outfit is in a light tone. Additionally, you can mix and match the sporty style, academic style, and dressy items to create a new look!


I personally think Keds Champion Originals Lace Up is a decent one. The design of these sneakers is very elegant, and I love that they are purely white! But that’s just my personal taste. You can find the white sneakers that you like regardless of the brand. If you already have one, then you don’t have to!

Riding Boots

Preppy fashion is also inspired by equestrian outfits since equestrianism is one of the activities that preppies like to do. (I briefly mentioned that when I talked about gloves earlier) As part of equestrian outfits, riding boots will help you complete various equestrian style preppy outfits that look extremely chic!

Moreover, you can wear riding boots even if it’s not for an equestrian look. Think of them as regular boots and try styling them with other preppy wardrobe essentials. You may accidentally create a cool preppy outfit! By the way, no need to wear professional riding boots. Wearing similar boots (knee-high boots with a round toe and low heel) will be fine!


Those are the best preppy wardrobe essentials that I want to recommend to you. (I know it’s a lot!) With those essentials, you will be able to create a couple of basic preppy outfits that look classic and stylish. I hope this post inspires you to create your own preppy capsule wardrobe, and I hope you have fun building it!

Some of the links in this post are affiliate links. This means if you click on the link and purchase the item, I will receive an affiliate commission(No Additional Charge to You). The commission I earn will be used for creating great content in this blog and thank you for your support.

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