Are you finding it challenging to combine a casual-chic look with a touch of sophistication during the fall season? The answer to your fashion problem is a preppy outfit! This timeless and versatile classic style makes it easy to effortlessly transition from a laid-back day look to a more polished evening ensemble. Fall outfits can be effortlessly elevated by incorporating preppy elements like tailored blazers, crisp button-downs, and stylish loafers. In this blog, you will learn how you can effortlessly infuse preppy outfit elements into your wardrobe to curate your finest looks and elevate your style.

If you want to infuse a touch of sophistication into your ensemble, WhatColors’ AI personal color analysis app could be your new best friend. This valuable tool is designed to help you decipher the ideal shades that complement your complexion and elevate your style game.

Table of Contents

• What Is a Preppy Outfit?

• 5 Must-Have Elements to Recreate the Preppy Style

• 8 Do's and Don'ts of Preppy Style

• 31 Ever-Green Preppy Outfit Styling Ideas to Try in Fall

• A New Preppy Style Fall Capsule Wardrobe

• How To Style Your Outfit The Preppy Way into Different Occasions

• Try AI Personal Color Analysis For Free Today
  

What Is a Preppy Outfit?

The preppy style originated in the 1950s, focusing on Ivy League schools and affluent lifestyles. This style was about:

• Clean lines

• Classic cuts

• Polished appearance

Preppy fashion's typical colors and patterns include navy, khaki, plaids, and pastels. The style focused on a timeless appeal and was associated with higher education and wealthy backgrounds.

Evolution of Preppy Style

The preppy style evolved, adapting to modern fashion trends and technological advancements. Previously, preppy fashion was exclusive and less accessible due to limited distribution channels.

With the rise of the digital space and globalization, preppy style has become more accessible globally. Designers like Tory Burch and Thom Browne have influenced the aesthetic, making it more legible and prevalent. Today, preppy fashion is more accessible and resonates with a broader audience.

Preppy Fashion Today

Preppy fashion has made a significant comeback, resonating with younger and more fashionable audiences. 

Color

Designers now offer a more comprehensive range of colors and styles, departing from the traditional camel, red, navy, gray, and white palette. 

Preppy Essence

Despite some high-end interpretations of preppy fashion, the essence of preppy style remains frugal and based on understated luxury. 

Preppy's Global Reach

In times of uncertainty, preppy fashion serves as a form of comfort and a way to convey status. The global appeal of preppy style is evident in various interpretations by designers worldwide, blending traditional elements with modern aesthetics.

5 Must-Have Elements to Recreate the Preppy Style

1. Crisp Button-Down Shirts

A crisp white button-down shirt is a quintessential piece in any preppy wardrobe. It's versatile, timeless, and effortlessly chic. Opt for a tailored fit to maintain a polished appearance and pair it with chinos or a pleated skirt for a classic preppy look.

2. Navy Blazer

A navy blazer is a must-have item for nailing the preppy look. It adds a touch of sophistication to any outfit and can be dressed up or down. Choose a structured blazer in a high-quality fabric like wool or cotton for a polished appearance.

3. Khaki Pants

Khaki pants are a staple in the preppy wardrobe. They are versatile, comfortable, and easily dressed up or down. Opt for a slim fit for a modern twist or a classic fit for a timeless look.

4. Sweater Vests

Sweater vests are a fun and stylish addition to a preppy outfit. They add a layer of warmth and texture to your look while exuding a classic collegiate vibe. Choose a sweater vest in a traditional pattern like argyle for an extra preppy touch.

5. Rugby Shirts

Rugby shirts are a fun and sporty addition to a preppy wardrobe. They add a pop of color and pattern to your outfit while maintaining a casual yet polished appearance. Pair a rugby shirt with chinos or a pleated skirt for a preppy-chic look.

Tips on Choosing the Right Color, Fabric, or Fit

• Stick to a neutral color palette with pops of bright colors for a preppy aesthetic.

• Choose high-quality fabrics like wool, cotton, or cashmere for a polished appearance.

• Opt for tailored fits for a sophisticated look and classic silhouettes for a timeless vibe.
  
  

Discover Your Palette with WhatColors

WhatColors helps you find what colors to wear based on your skin tone. Unlock your colors and transform your style with WhatColors’ AI Personal Color Analysis app. 

Instant Color Analysis

With WhatColors’ AI personal color analysis app, you can complete your color analysis within 60 seconds. Download our app for free today on the App Store or Google Play store.

Related Reading

• Fall Family Outfits
• Fall Engagement Photo Outfits
• Plus Size Fall Outfits
• Mens Fall Outfits
• Fall Brunch Outfits
• Fall Date Night Outfits
• Casual Fall Outfits
• Fall Golf Outfits
• Fall Skirt Outfits
• Fall Wedding Outfits
• Fall Picture Outfits

8 Do's and Don'ts of Preppy Style

1. Embrace the Classics

When it comes to preppy fashion, classics are your best friends. Embrace the enduring charm of:

• Polo shirts

• Khaki pants

• Shift dresses
  
  

These pieces are the backbone of preppy style, and you can mix and match them endlessly to create refined and laid-back outfits.

2. Overdoing the Logos

We get it – you love your favorite brands. But in the preppy world, subtlety is key. Avoid drowning yourself in logos from head to toe. 

Opt for understated elegance rather than turning into a walking billboard. Let your style speak for itself without shouting brand names.

3. Play with Patterns

Preppy fashion is the perfect playground for patterns. Stripes, checks, and plaids are your pals. Mix them up, but remember to balance bold patterns with solid pieces to avoid going overboard. It's all about finding that sweet spot between lively and refined.

4. Tailoring Matters

A well-fitted garment can make all the difference. Whether it's a blazer, a pair of chinos, or a sundress, ensure your clothing hugs you in all the right places. 

Avoid drowning in oversized pieces or squeezing into something too tight. Tailoring is the secret weapon of the preppy elite.

5. Invest in Quality Basics

Quality over quantity, my friends. Invest in pieces that stand the test of time. A well-made blazer or a classic trench coat isn't just a purchase.

It's a lifelong commitment to looking fabulous. Build your preppy wardrobe with pieces that can weather both trends and seasons.

6. Shy Away from Colour

Preppy fashion is like a vibrant painting, but it is also all about aesthetics, and the color is your palette. Feel free to infuse your wardrobe with bright hues.

Whether it's a pop of coral or a splash of mint green, color adds personality to your preppy canvas.

7. Incorporate Accessories Thoughtfully

Accessories are the exclamation point to your preppy sentence. A sleek watch, a statement belt, or a tasteful headband can elevate your look. Just remember, it's about the details, not the excess. Less is often more in the preppy playbook.

8. Mix Too Many Trends

Preppy fashion has a rhythm, so avoid catching up on every passing trend. While it's fun to experiment, only a few trends in one outfit can lead to a style cacophony. Stick to the timeless elements and sprinkle in trends sparingly.

Related Reading

• Fall Concert Outfits
• Fall Senior Picture Outfits
• Fall Date Outfits
• Fall Pregnancy Outfits
• Fall Birthday Outfits
• Fall Office Outfits
• Trendy Fall Outfits
• Preppy Fall Outfits
• Fall Church Outfits
• Fall Baby Shower Outfits
• Fall Teacher Outfits
• Cozy Fall Outfits
• Fall Game Day Outfits

31 Ever-Green Preppy Outfit Styling Ideas to Try in Fall

1. Proud Monograms

Adding a touch of personality to your fall look with a monogrammed pullover sweatshirt is an excellent way to infuse preppy style into your wardrobe. 

Collegiate font patches can elevate a simple sweatshirt, creating a varsity-inspired, cozy, and stylish look. Pair this monogrammed sweatshirt with jeans or tailored pants for a casual yet polished ensemble.

2. Cher Horowitz-Inspired Plaid

Channel your inner Cher Horowitz by incorporating a yellow plaid mini skirt into your fall wardrobe. This '90s-inspired piece can be styled with a graphic knit for a modern twist. 

Embrace the preppy aesthetic by pairing this plaid skirt with knee-high socks and loafers for a chic and sophisticated look.

3. Vintage-y Cable Knit

Opt for a classic red cable knit sweater this fall to achieve an effortlessly preppy outfit. Pair it with jeans for a casual vibe, or dress it with trousers and loafers for a more polished look. 

Consider adding edgy accessories like combat boots and a trendy shoulder bag to balance this outfit's traditional preppy elements.

4. Cool in Crimson

Layer a white button-down shirt under a logo t-shirt for a preppy look with a pop of color. 

Incorporate cherry red accessories like a handbag or scarf to add visual interest to your outfit.

This ensemble strikes the perfect balance between classic preppy elements and contemporary style.

5. Trouser Shorts

Transition into fall with long plaid shorts paired with a relaxed button-down shirt. Taking cues from Barbie Ferreira's style, this outfit exudes a:

• Modern preppy

• Comfortable

• Chic vibe

Complete the look with statement accessories like a chunky belt and platform shoes.

6. Sweater (Vest) Weather

For those days when you want to be comfortable yet stylish, layer a sweater vest over a button-down shirt. 

This combination is perfect for achieving a preppy look without sacrificing comfort. Pair this outfit with leggings and loafers for a cozy yet sophisticated ensemble.

7. Preppy Prints Turned Cozy

Elevate your fall outfits by incorporating trousers into your wardrobe. Pair them with a cozy cardigan for a laid-back yet preppy look suitable for various occasions. 

This outfit effortlessly combines sophistication with comfort, making it a versatile choice for the season.

8. Plaid on Plaid

Make sure to mix prints this fall. Take inspiration from Hailey Bieber and create a monochrome look with classic plaid patterns in shades like:

• Grey

• Black

• White
  
  

Embrace the preppy aesthetic by layering different plaid pieces and adding polished accessories like:

• Leather belts

• Structured handbags
  
  

9. Belts, Caps, and Bags

Accessories play a crucial role in enhancing your preppy outfits. To elevate your ensembles, opt for classic leather belts, cabby hats, and structured bags.

These timeless accessories add a sophisticated touch to any outfit, making them essential elements of preppy style.

10. Gothic Peacoat

Experiment with different styles by pairing preppy items like a peacoat with edgy details. Incorporate Victorian goth elements like leather boots to create a unique, fashion-forward look. 

This outfit showcases the versatility of preppy style, allowing you to express your individuality while staying true to the classic aesthetic.

11. Varsity Jacket

Sift through your local thrift store (or raid your dad's closet) for a retro letterman jacket that gives off all the preppy feels. Pair it with a vintage concert tee and pants.

12. Nautical Cardigan

This is the ultimate preppy outfit. An oversized stripe-trim cardigan adds effortless elegance to a white tee and jeans. Keep accessories low-key so the sweater steals the show.

13. Clean White Turtleneck

A fitted white turtleneck is a tried-and-true preppy favorite. You can layer it under your favorite sweater, tuck it into high-waisted jeans, or double down on preppy vibes with a nautical striped skirt.

14. Updated Penny Loafers

Make your classic penny loafers feel fashionable with cropped jeans and cute striped socks. Adding a pair of black slip-on loafers instantly transforms any outfit into a preppy one.

15. A Classic Varsity Sweater

Nothing says preppy like a classic Lacoste varsity knit. Wear your oversized with slim joggers, or dress it up with a slim trouser and boots.

16. Sweater Vests are Your New BFF

Sweater vests have been big news recently, and we’re obsessed. This petite knitwear is the perfect finishing touch for a ’90s preppy outfit. 

Don’t be afraid to go retro and channel your inner Carlton from The Fresh Prince to this preppy outfit idea. Wear a checked sweater vest over a polo top or shirt and team with tailored trousers for a cute preppy outfit. 

You can also tone down this outfit idea by ditching the prints and opting for plain neutral tones – which is great if you’re a fan of the vanilla girl trend.

17. Wear Your Jumper Over Your Shoulders

Sometimes, it isn’t what you wear that matters, but how you wear it. Take the humble jumper, for example. 

Draped Knits

Draping your knits over your shoulder is the perfect way to give even the simplest outfit a cute, preppy spin. 

Styling Tips

The trick to getting this look right is keeping your whole outfit simple and ensuring you’re draping your jumper over a casual t-shirt or polo neck top rather than your bulky winter coat. 

Practical Chic

Plus, if it suddenly gets cold or you want to cozy up, you’ve got an extra layer to hand - ideal if you’re dressing for the airport.

18. Pair Socks with Your Mini

If there is one combo that we will always associate with the 90s preppy aesthetic, it is the mini skirt and knee-high socks (bonus points if it is a pleated skirt). 

Preppy Confidence

This classic preppy outfit idea may seem a bit daunting and bring back memories of your school uniform, but trust us when we say it is more wearable than you’d think—you just need to keep it simple and wear it with confidence. 

Summer Preppy

And if getting your legs out feels a little too daunting, switch to a midi-length skirt teamed with a polo top and sunnies for a cool preppy summer outfit.

19. Loaf-Ing Around

If there is one shoe you should invest in to nail the preppy trend, it is the oh-so-versatile loafer. This shoe-drove classic will instantly give any outfit a preppy spin – even if that outfit is as simple as jeans and a chic shirt. They’re very comfortable and ideal for running errands around town.

20. Suit Up Your Hoodie

Wearing a hoodie underneath your tailored coat gives your outfit a street-style-inspired update. This ensemble is super comfortable and makes your suit feel more daytime-appropriate—perfect if you’re going out for lunch or on a coffee date.

21. Embrace the Bomber Jacket

Bomber jackets are set to be huge in the 2020s, so ditch your denim and biker jackets in favor of this retro style. 

Bomber Basics

The best bit about this new jacket trend is that you have fun and play with colors. Try keeping it simple and wearing your bomber over sneakers, jeans, and a tee for an effortless daytime look. 

Feminine Flair

Or try pairing a bomber over a mini skirt or dress and sneakers if you prefer to create more of a feminine, cute, preppy outfit.

22. Vest, Mini Skirt & a Tie

Nothing screams preppy style like a tie! It’s an easy way to add a preppy touch to your classic outfits. Wear it with a blazer, knit vest, or mini skirt. Don’t forget to finish off the look with chunky loafers and socks.

23. Tennis Skirt and Sweatshirt

A tennis skirt is a staple for your preppy aesthetic wardrobe. Pair with a collared sweatshirt, or simply layer a white shirt underneath. Finish the look with a white headband and some accessories.

24. Pleated Skirt & Trainers

How stunning is this outfit? The red bag adds the perfect touch of color, and the pearl necklace just adds a super chic element to the look. If you want to recreate this outfit in winter, it’s always a good idea to layer a turtleneck sweater underneath for extra warmth. 

25. Stripes & a White shirt

Changing from loafers to ballerina flats is such a stunning outfit. Layer a striped sweater over a shirt dress, or pair it with a pleated skirt and layer a white shirt underneath. Stripes are synonymous with the preppy style and add a chic touch to any outfit.

26. White Shirt & Pleated Skirt

This is such an easy look to recreate. You can wear it year after year, and it will always stay in style because it incorporates classic pieces. 

Preppy Finish

Pair a white shirt with a grey pleated skirt, and finally, add a pair of heeled loafers and socks to tie the look together and give it a preppy vibe.

Adapting the Style for Men

The key to mastering preppy fashion for men is a blend of sophistication, a sprinkle of playfulness, and a dash of that effortlessly cool attitude.

27. Tailoring is Your Wingman

When it comes to preppy fashion, the fit is everything. Invest in well-tailored pieces that complement your body shape. 

A crisply tailored blazer can turn a casual outfit into a style statement, and well-fitted chinos are your ticket to that laid-back yet polished look.

28. The Quintessential Button-Down

Every preppy wardrobe needs a squadron of button-down shirts. Crisp whites, pastel blues, and subtle patterns are your go-tos. 

These versatile shirts can seamlessly transition from a casual day at the office to a weekend brunch without missing a beat.

29. Polo Shirts for the Win

Polo shirts are the workhorses of preppy style. Opt for high-quality fabrics and classic colors. They're a smart choice for casual outings, and you can even dress them up with a blazer for a more refined look.

30. Footwear Matters

For your feet, it's all about the classics – loafers, boat shoes, and clean white sneakers. Each pair adds flair to your preppy ensemble. Boat shoes, in particular, are like the cherry on top of your nautical-inspired look.

31. Accessorize with Purpose

Remember to underestimate the power of accessories. A well-chosen belt, a sleek watch, or a classic tie can elevate your outfit from good to exceptional. Choose pieces that complement your look without overwhelming it.

A New Preppy Style Fall Capsule Wardrobe

New preppy fashion is more relaxed, a bit slouchy, more contradictory, and often with a balance between menswear and women’s wear. You should never feel like you aren’t rich enough or fancy enough to wear a particular piece. 

Preppy Perception

This isn’t about social class. You can wear whatever you want. It is said that Andy Warhol and his boyfriend wore preppy clothes not as a sense of personal style but as a kind of costume—something to make them fit in and live openly in a society that had animosity toward LGBTQ+ people. 

Modern Preppy

This modern prep is about perverting the typical ideals of the traditional world of preppy fashion. It is like the person wearing these classic pieces is taking the ideals typically associated with them and messing with them.

Camel Coat

In order to embrace this new prep, you must use this classic style in unusual, exciting, and provocative ways.

• Try to tuck your trousers into cowboy boots, moto, or tall boots, but keep everything else complete: preppy clothes. 

• Try grey jogging pants tucked into slouchy socks and worn with loafers.

• Pair them with a knit turtleneck and a tweed blazer for a casual preppy look. 

• Belts should be considered accessories, not utilitarians. 

• Wear your knee-length, button-front coat like a dress, paired with tights and Mary Janes.
  
  

Plaid Trousers

• Balance menswear and women’s wear by pairing a midi skirt with a men’s sweater and loafers or boots.

• Add visual interest with a belt bag or quirky jewelry. 

• Layer a shirt dress under a skirt with a high slit so the dress shows through the slit, and the top looks like a button-down. 

• Keep it collegiate on top with a blazer over a university sweater or sweatshirt, and party down below with a tulle or flouncy skirt for the extra vibe—an oversized rugby shirt paired with wide-leg trousers, bold accessories, and ballet flats.
  
  

Classic Loafers

Layering a sweater over a sweater:

• Put the more fitted sweater underneath, then slouch the sleeves of the more relaxed sweater on top to see the underneath sweater. 

• Wear long leather gloves under a button-down or sweater with the sleeves pushed up.

• Add a bit of retro with a track jacket zipped up and layered under a blazer with trousers.

• Go the opposite and wear track pants with otherwise altogether preppy clothes.
  
  

Button-Down Shirt

Bold shoulder pads in menswear-inspired coats. 

• A pretty print cardigan buttoned up and worn as a shirt over loose-fitting trousers.

• Everything is just a tad more relaxed, exaggerated, messy, or slouchy. 

• When in doubt, go one size larger. 

• Use a tie as a belt, or tie your sweater or cardigan around your waist to mimic a skirt.
  
  

Personalize Your Preppy

The key to mastering the preppy style is to customize it with your unique touch.

• Incorporate some unexpected elements, mix and match the classic pieces, and always remember to have fun with your outfits. 

• Try this new preppy style, and let your creativity shine through your fall wardrobe.

How To Style Your Outfit The Preppy Way into Different Occasions

Now that you've got the preppy basics down, let's talk versatility. Preppy fashion isn't just for one setting; it's a chameleon that seamlessly adapts to various occasions. 

Whether you're brunching with friends, attending a business meeting, or heading to a formal event, preppy style has your back—and it looks good doing it.

Casual Outings

For those laid-back weekends or coffee catch-ups, keep it casual yet polished. Ladies, pair a crisp white button-down with tailored shorts or a knee-length skirt. Add a pop of color with your accessories, and you're ready to take on the day. 

Gentlemen, opt for well-fitted chinos and a polo shirt for a look that effortlessly straddles casual and refined.

Business Casual

Ladies, a tailored blazer over a button-down shirt and a pencil skirt is a power move. Accessorize with a sleek watch and classic pumps. 

Gentlemen, elevate your business casual game with a well-tailored suit in classic colors. Ditch the tie for a more relaxed feel while still exuding professionalism.

Outdoor Gatherings

Preppy fashion is proper at home, whether it's a garden party or a barbecue. Ladies, a floral dress paired with espadrilles or wedges is a winning combination—a sun hat for that extra touch of elegance. 

Gentlemen, embrace light-colored chinos or shorts with a crisp short-sleeved shirt. Boat shoes are the perfect finishing touch for an outdoor affair.

Formal Events

Yes, preppy style can gracefully waltz into formal events. Ladies, a well-tailored shift dress in a solid color or subtle pattern is a sophisticated choice. 

Add a string of pearls and heels, and you're red carpet ready. Gentlemen, opt for a classic navy blazer paired with tailored trousers and a dress shirt. A silk tie or bowtie completes the ensemble, ensuring you stand out in the sea of suits.

Beachside Vibes

If you find yourself by the coast, preppy fashion fits right in. Ladies, a breezy sundress in a nautical stripe or pastel hue paired with sandals is the epitome of seaside chic. 

Gentlemen, wear well-fitted shorts with a lightweight button-down shirt—leave it untucked for a relaxed beach vibe. Boat shoes or stylish sandals are the go-to footwear for coastal cool.

Related Reading

• Fall Transition Outfits
• Fall Outfits With Boots
• Fall Party Outfits
• Fall Outfits For School
• Fall Couple Outfits
• Warm Weather Fall Outfits
• Fall Dinner Outfits
• Fall Outfits For Teens
• Modest Fall Outfits
• Fall Hiking Outfits
• Outfit Ideas
• Fall Outfit Inspo
• Fall Outfit Men
• Fall Outfit Women
• Cute Fall Outfit Ideas
• Fall Dresses for Women

Try AI Personal Color Analysis For Free Today

WhatColors aids in finding the ideal colors to wear based on your skin tone, helping you discover your season using the patented color match technology. 

Color Harmony

By analyzing your skin, eye, and hair color, WhatColors offers the perfect colors to complement your natural features. 

Color No-Nos

Based on your specific color profile, you can identify colors to avoid. WhatColors offers a nail color generator to help you find the perfect nail colors to match your skin tone. 

Nail It

Get your personalized color analysis within 60 seconds with the WhatColors' AI personal color analysis app, available for free on the App Store and Google Play store. Download the app today to embrace the colors that enhance your natural beauty.