25 Wealthy-Looking Preppy Outfit Ideas That Feel Old Money

Discover in this post the best preppy outfit ideas.

Are you looking for stunning preppy outfit ideas? If yes, you’re in the right place! Preppy style is all about structured silhouettes, timeless pieces, and classic patterns, such as stripes, plaid, tweed, and argyle.

You don’t need flashy logos or extravagant designs to achieve this aesthetic. The secret is to combine tailored clothing and neutral shades to create a refined and luxurious look.

From pleated skirts and fitted blazers to cable knit sweaters and wool coats, there are so many ways to build outfits that feel sophisticated!

Discover 25 elegant preppy outfit ideas that will make you look chic and confident.

Preppy Outfit Ideas

Get inspired by these 25 trendy preppy outfit ideas to feel classy and wealthy!

1 – A Blue Striped Shirt With A White Sweater And Cream Shorts

A preppy outfit.

Source: Instagram, ©styledbyvienne

Pair a blue striped Ralph Lauren shirt with a white knit on your shoulders and cream shorts to create a refined and soft preppy outfit.

Accessorize this look with cream ballet flats, a black handbag, a light blue headband, and pearl jewelry for a feminine and delicate touch.

2 – A Plaid Blazer With White Pants

A preppy outfit.

Source: Instagram, ©evepecak

Pair a light brown plaid blazer with white tailored pants and light brown suede ballet flats to feel cozy and chic this spring.

Accessorize your outfit with a brown handbag and gold jewelry for a refined and luxurious touch.

3 – A Cream Cropped Blazer With A White Shirt And A Short Cream Skirt

A preppy outfit.

Source: Instagram, ©biancadiariesx

Combine a cream cropped blazer with a white shirt, a short cream plaid skirt, white socks, and brown loafers to look feminine and classy.

Accessorize your outfit with a black handbag and gold earrings for a glam and powerful touch.

4 – A Gray Sweater With A White Shirt And A White Pleated Skirt

A preppy outfit.

Source: Instagram, ©leximars

Layer a white shirt with a gray knit sweater. Wear them with a white pleated skirt, white socks, and black loafers to create a cute and soft spring outfit.

Accessorize your preppy look with gold jewelry to give it a classy and refined feel.

5 – A Light Pink Tweed Dress With A White Turtleneck Top

A preppy outfit.

Source: Instagram, ©lavinia.td

A short, light pink tweed dress will make you look so soft and feminine! Layer it with a white turtleneck top and cream boots for a delicate and dreamy touch.

Lastly, accessorize your preppy outfit with a cream handbag and silver jewelry to give it a luxurious feel.

6 – A Navy Sleeveless Sweater With A White Shirt And A Short Gray Pleated Skirt

A preppy outfit.

Source: Instagram, ©katviras

Layer a navy sleeveless cable knit sweater with a white shirt. Choose a v-neck knit for an even more wealthy and classy look!

Wear them with a short gray pleated skirt, white socks, and black loafers for a cute and feminine touch.

Lastly, accessorize this look with a silver handbag and silver jewelry to give it a fashionable and stylish feel.

7 – A Light Pink Cardigan With A Short White Pleated Skirt

A preppy outfit.

Source: Instagram, ©chiara.casiraghi

Combine a light pink Ralph Lauren cable knit cardigan with a short white pleated skirt and white ballet flats to feel feminine and classy this summer.

Accessorize your outfit with a woven handbag and silver jewelry for a radiant and elegant touch.

8 – A Blue Striped Shirt With White Shorts

A preppy outfit.

Source: Instagram, ©sophielouisesdiary

Pair a blue striped shirt with white tailored shorts, a brown belt, and white ballet flats to look classy and elegant.

Accessorize your preppy outfit with a brown handbag and minimal jewelry for a refined and confident touch.

9 – A White Tweed Dress

A preppy outfit.

Source: Instagram, ©sophielouisesdiary

A white tweed dress will make you feel so classy and sophisticated! Wear it with white low heels, a cream handbag, and gold jewelry for a feminine and luxurious touch.

10 – A Navy And White Striped Shirt With A Navy Skirt

A preppy outfit.

Source: Instagram, ©thejoanadias

Combine a navy and white striped shirt with a navy knit on your shoulders and a short navy skirt to look wealthy and classy.

Accessorize your preppy outfit with navy ballet flats, a brown handbag, and minimal jewelry for a refined touch.

11 – A Light Blue Tweed Jacket With A Light Blue Sweater And White Tailored Pants

A preppy outfit.

Source: Instagram, ©aaagistyle

Pair a light blue knit with a light blue tweed jacket and white tailored pants to feel feminine and elegant.

Accessorize your outfit with white heels, a white handbag, and pear earrings for a luxurious and sophisticated touch.

12 – A Black Blazer With A Black Turtleneck Top And White Skinny Jeans

A preppy outfit.

Source: Instagram, ©ellizabethh

Mix a black blazer with a black turtleneck top, white skinny jeans, and black knee-high boots to create a refined equestrian outfit.

Accessorize this look with a black handbag and a gold necklace for a classy touch.

13 – A White Cardigan With A Short Plaid Skirt And A Trench Coat

A preppy outfit.

Source: Instagram, ©chlce

Pair a white cardigan with a short plaid skirt, a trench coat, white socks, and red Mary Janes to feel feminine and elegant.

Accessorize your preppy outfit with a red handbag and gold jewelry for a bold and confident touch.

14 – A Taupe Blazer With A Short Camel Pleated Dress And A White Shirt

A preppy outfit.

Source: Instagram, ©keziacook

Combine a taupe blazer with a short camel bustier pleated dress, a white shirt, and brown ballet flats to look classy and elegant this fall.

Lastly, accessorize your outfit with a red handbag and gold earrings for a striking touch.

15 – A Brown Sweater With A Blue Shirt And A Cream Pleated Skirt

A preppy outfit.

Source: Instagram, ©taniabyday

Layer a brown cable knit sweater with a blue shirt. Wear them with a cream pleated skirt, white socks, and brown suede loafers to create a cute and feminine fall preppy outfit.

Accessorize this look with a brown handbag and pearl earrings to give it a classy feel.

16 – A Camel Blazer With A Black Top And White Striped Pants

A preppy outfit.

Source: Instagram, ©allchloerose

Pair a camel blazer with a black top, white striped pants, and brown loafers to feel classy and wealthy.

Accessorize your preppy outfit with a brown handbag and a silk bandana around your neck for a chic touch.

17 – A Camel Sweater With A White Shirt And A Short Black Skirt

A preppy outfit.

Source: Instagram, ©d.angelgomez_m

Combine a camel v-neck cable knit sweater with a white shirt, a short black skirt, white ruffled socks, and black Prada loafers to create a wealthy-looking preppy outfit.

Accessorize this look with a black Chanel handbag and gold jewelry for a luxurious touch.

18 – An Argyle Sweater With A Short White Skirt

A preppy outfit.

Source: Instagram, ©peytonjohnsonnn

Mix an argyle sweater with a short white skirt and cream suede knee-high boots to feel feminine and chic.

Accessorize your preppy outfit with a cream handbag and gold earrings to give it a classy and refined touch.

19 – A Navy Cardigan With A Black Pleated Skirt

A preppy outfit.

Source: Instagram, ©timeless_chicgirl

Combine a navy cardigan with a white shirt, a short black pleated skirt, and black loafers to look chic and classy!

Accessorize your outfit with a black handbag and silver earrings for a refined and luxurious touch.

20 – A Burgundy Plaid Blazer With Gray Leggings And Burgundy Boots

A preppy outfit.

Source: Instagram, ©style.saus

Pair a burgundy satin blouse with a burgundy plaid blazer, gray leggings, and burgundy boots to create a bold and feminine equestrian outfit.

Accessorize your preppy look with a burgundy handbag and gold earrings for a refined touch.

21 – A Camel Coat With An Argyle Cardigan And Navy Pants

A preppy outfit.

Source: Instagram, ©jlknnifer

Combine a camel wool coat with an argyle cardigan, navy pants, and brown loafers to feel classy and chic!

Accessorize your outfit with a camel Jacquemus handbag and gold earrings to give it a wealthy and luxurious feel.

22 – A Burgundy Sweater With Plaid Shorts

A preppy outfit.

Source: Instagram, ©chocolat.marie

Pair a burgundy sweater with plaid shorts, a burgundy houndstooth scarf, burgundy socks, and brown loafers to look cute and elegant this winter!

Accessorize your preppy outfit with a cream knit handbag and gold jewelry for a cozy and classy touch.

23 – A Brown Wool Coat With A Gray Sweater And Black Shorts

A preppy outfit.

Source: Instagram, ©svenjagzer

Layer a white shirt with a black tie and a gray knit sweater. Wear them with a long brown wool coat, black shorts, a black belt, and black pointy heels to create a sophisticated and refined winter preppy outfit.

Accessorize this look with a brown handbag, black faux leather gloves, and gold earrings for a bold and powerful touch.

24 – A Black Faux Fur Trim Jacket With A Short Brown Dress

A preppy outfit.

Source: Instagram, ©charlotteannaw

Combine a black faux fur trim jacket with a short brown plaid dress, a black belt, and brown boots to feel old money!

Accessorize your outfit with a brown handbag and gold jewelry for a classy touch.

25 – A Red Wool Coat With A Navy Cardigan And Black Shorts

A preppy outfit.

Source: Instagram, ©holajoannekennedy

Pair a red wool coat with a navy and red knit cardigan, black shorts, a black belt, and black knee-high boots to create a refined and classy winter outfit.

Accessorize your preppy look with a black handbag and gold jewelry for a luxurious touch.

FAQs

What Is Preppy Style?

Preppy style is inspired by classic Ivy League fashion and combines tailored pieces, timeless patterns, and refined color palettes to create sophisticated outfits.

What Colors Are Best For Preppy Outfits?

Neutral shades, such as white, cream, navy, gray, brown, and black, are essential. Soft pink, baby blue, burgundy, and forest green will also enhance the preppy aesthetic.

What Patterns Make An Outfit Look More Preppy?

Plaid, stripes, argyle, tweed, and houndstooth patterns will instantly create a classy and refined preppy look.

What Shoes Go Well With Preppy Outfits?

Loafers, ballet flats, Mary Janes, knee-high boots, and pointy heels are perfect to complete a preppy outfit.

Can You Wear Preppy Outfits Casually?

Yes! Pairing tailored pieces, such as blazers or pleated skirts, with simple knit sweaters or classic shirts will create relaxed yet refined everyday looks.

What Fabrics Look The Most Preppy?

Tweed, wool, knit, cotton, and structured fabrics will instantly elevate your outfit and give it a wealthy feel.

Conclusion

With these 25 cute preppy outfit ideas, you will be able to create timeless looks for every season.

Preppy fashion is all about structured silhouettes, refined fabrics, and harmonious color combinations. Classic patterns, such as plaid, stripes, and argyle, will instantly enhance your outfits.

Don’t hesitate to layer blazers, cardigans, and wool coats to add depth and sophistication to your look. With the right combinations, you will effortlessly create outfits that feel confident and truly old money.

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Hi, I'm Anna!

Welcome to Hastralys! This blog is for women who love elegant fashion, outfit ideas and accessories. Feel more confident in yourself with weekly ideas and inspiration!
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