preppy aesthetic outfit

Preppy Aesthetic Outfit Ideas for Elevating Your Looks

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The world of preppy aesthetic outfits is all about blending classic charm with touches of modern flair, making for timeless looks that have stood the test of time in more ways than one. Trends come and go, but features of the preppy aesthetic have often found their way back to the spotlight – sometimes showcased in other styles. (Classics never truly go out of style.) If you haven’t experimented with this particular style before, stepping into such a popular aesthetic can feel like compromising on your own personal style, but there are many ways around that! Whether you are already a lover of the preppy style or just now getting into it with me, get ready to incorporate a few new go-to outfits into your closet.

1. wool pants + stripe button-up shirt + cashmere crewneck + sandals + handbag + sunglasses

preppy aesthetic outfit

pants | shirt | sweater | sandals | bag | sunglasses

Can you tell spring is on my mind? This first outfit is a great way of welcoming the new season, blending some cold weather and hot weather pieces for a balanced preppy look. 

Start off with these Italian wool pants, perfect for still keeping yourself somewhat warm while showing off the beautifully tailored look of the trousers. For your top, there is nothing quite like a good striped, crisp button-down shirt to welcome the warmer weather.

This versatile piece can easily transition from the office to your weekend brunch – all it takes is a little styling! For this look, make sure to tuck in your shirt and roll your sleeves. Open up a few buttons as well for a more relaxed, laid-back look that screams preppy.

Tie this beautiful beige cashmere sweater over your chest for an elegant way to stay warmer and prepared for when the wind hits. Here, accessories are crucial for the final look to hit its full potential. Add an oversized pair of brown sunglasses, along with a structured crossbody bag and a pair of summer-ready, elegant sandals. 

By coordinating your accessories to follow one particular color palette, you are making sure that your look comes together a lot more smoothly! 

2. miniskirt + t-shirt + collared sweater + shoulder bag + gold watch + loafer + socks 

preppy aesthetic outfit

miniskirt | t-shirt | sweater | bag | watch | shoes | socks 

It turns out that trendy and classy do get to go together sometimes! This preppy outfit takes timeless pieces and a more modern styling approach, bringing these two elements together into one cute look. 

Begin with this knitted miniskirt, one of the most popular pieces out there when it comes to the preppy aesthetic! On top, a simple fitted white tee will do the trick, keeping things sleek and simple.

For a subtle but charming pop of color, layer this organic cotton collared sweater on top of your shirt. Not only does the collar detail tie back into the aesthetic we’re aiming for, but the silhouette of the sweater also beautifully complements the shorter proportions of the skirt. 

Again, accessories are a must here as they really emphasize the mood of the outfit and bring it all together. A simple and chic black handbag, along with a black pair of loafers tie in with the skirt and balance out the color palette of the look.

More subtle touches like a pair of white socks and a gold watch finish off the look with beautiful delicate details that bring it all back to the preppy aesthetic as well.  

3. sweater vest + poplin shirt + wide-leg wool pants + pumps + hoop earrings

preppy aesthetic outfit

sweater vest | shirt | pants | pumps | earrings 

Making for a less trendy take on the preppy aesthetic, this outfit still finds a way to seamlessly integrate more contemporary aspects into this otherwise classic look. 

These wide-leg pants make a statement with their gorgeous shade of brown and subtle plaid pattern, bringing depth and interesting proportions to the look. While plaid mini skirts tend to be a more common way of seeing this pattern in classic preppy style, finding them in other pieces like trousers is a great way of diversifying your collection! On top, a basic button-up collared shirt is the perfect pair, bringing a more traditional element into the mix.

On top of your shirt, layer this checkered stitch sweater vest. The pattern on this piece speaks to the plaid pattern on the pants, tying both pieces together efficiently but in a subtle way that’s not too overpowering, either. 

Bring out the collar of your shirt on top of your sweater, and make sure to roll up the sleeves slightly for a casual styling touch that elevates the entire look.  

For shoes, these kitten heel pointed pumps play into the timeless and classic feel of this ensemble, while also adding some texture and a little extra flair with its chic design. As for accessories, leave the focus to the clothes and opt for an understated pair of bubble hoop earrings to bring it all together.

4. lady jacket + elbow-sleeve t-shirt + straight jeans + ballet flats + watch

preppy aesthetic outfit

jacket | t-shirt | jeans | shoes | watch

Lady jackets have my heart, and they definitely belong within the preppy aesthetic category too. From quickly dressing up a pair of jeans and a white tee to being the focus of an entire outfit, this piece is versatile in the best ways – and truly perfect for styling year-round!

More structured and polished than a knit cardigan, for example, lady jackets allow you to add structure and poise to the most basic of looks, regardless of the season.

…and that’s exactly what we’re going for here! This preppy look can also be considered French-inspired by many, as it uses a lot of elements that I love about French fashion

Take a break from your skinny jeans and experiment with a different denim fit by starting this look with these 90s straight jeans. This straight silhouette makes for just the right fit when it comes to a timeless and elegant pair of jeans – not too tight, and not too loose! 

On top, an elbow-sleeve t-shirt does the trick, offering slightly more coverage to keep you comfortable and warm. Layer your navy lady jacket on top, instantly adding that preppy charm to your ensemble. 

Opt for a delicate gold watch as your main accessory, elevating your outfit by giving it a more polished flair. As for shoes, these ballet flats will slip onto your feet easily, complementing both your look and your levels of comfort throughout the day. 

5. linen shorts + polo cardigan sweater + Mary Jane flats + cat-eye sunglasses + tote

preppy aesthetic outfit

shorts | sweater | shoes | sunglasses | tote

Yes, the preppy aesthetic can be confusing and lead to a lot of misconceptions from those who aren’t super familiar with the style – one of the main ones being that there is no such thing as a casual preppy outfit. While this is definitely not true, this outfit is here to officially disprove this theory and show you exactly how this simple look falls under the preppy aesthetic. 

More than just specific types of outfits or clothing pieces, the preppy aesthetic is about making use of classic styles and silhouettes for elegant overall ensembles. While these looks can definitely include a lot of accessories, for example, simplicity is also a way to be successful when it comes to finding the perfect preppy look.

For this look, we are starting with a pull-on linen short; this super easy-to-wear, breathable fabric lays the casual foundation of the look. On top, pair your shorts with this ribbed polo cardigan sweater. 

The slouchy fit of this piece matches the fit of the shorts, while also elevating the look with features like a collar and a striped pattern. Especially when it comes to putting together a stylish look filled with preppy clothes, relying on classic patterns is the best way to bring some variety to your collection while still keeping things neutral and timeless. 

For accessories, this look proves once again that simple doesn’t have to mean boring. This tote keeps all of your belongings safe while also adding some structure to this relaxed ensemble. Mary Jane shoes once again add another classic element to the look, finishing off a sleek preppy combination.

6. pleated linen short + button-down shirt + leather belt + cashmere sweater + ballet flat + tote bag

preppy aesthetic outfit

shorts | shirt | belt | sweater | shoes | tote

Bright colors can be super fun to incorporate into looks sometimes, but I have to say, neutrals have my heart! Also ideal for spring, this next outfit is a dream for anybody who loves classic neutral shades – and a pop of light blue.

These pleated linen shorts kick off the look. Shorts can often feel too casual if you are not used to styling them within this aesthetic, but there are many ways around this obstacle when it comes to crafting truly classic looks during the warmer months of the year.

Opting for fabrics like linen, for example, instantly adds a luxurious texture to your look, setting the tone for the outfit and balancing the more casual design of the shorts as well. On top, this blue button-down shirt continues to dress up the bottoms. Style your shirt by rolling up the sleeves and tucking it into your shorts for a better fit and overall look. 

Whether you wear your cashmere sweater tied draped over your shoulders, keep it inside your tote, or have it on, this piece can be integrated into this look a number of different chic ways. Bringing another classic tone into the neutral color palette of the outfit, this sweater adds a beautiful extra layer. 

This large tote bag matches the soft beige tone of the linen shorts, making for a cohesive and thought-out outfit that fits perfectly into the preppy aesthetic. A deeper brown shade makes for the perfect accessories – a skinny belt and a pair of beautiful ballet flats finish off this ensemble. 

7. chino shorts + button-up shirt + shoulder tote + slip-on sneaker + stud earrings

preppy aesthetic outfit

shorts | shirt | tote | sneakers | earrings

Hot weather shouldn’t get in the way of your style, and this next look shows you exactly how that can be done.

These chino shorts keep you cool while still very much giving off the preppy aesthetic with their cut and structure. In this beautiful navy color, this piece also features a higher rise and an elegant tailored look.

Button-down shirts are an absolute staple item for any preppy wardrobe, but sometimes the temperatures might get in the way – thankfully, there’s no need to worry! This bib button-up shirt keeps the look you love in this far cooler, more breathable short-sleeve version… talk about having the best of both worlds. Made from a herringbone twill fabric, this shirt still elevates your look through its materials and silhouette while definitely not compromising on your comfort. 

Add a touch of sparkle with these cubic zirconia studs, polishing your look even more. As for accessories, opt for this classic beige tote and a pair of comfortable white sneakers. The more casual shoe choice helps us to balance out the more elegant clothing pieces and keeps you comfortable throughout the day as you relax or run your errands for the week. 

8. wide-leg jean + button-up shirt + ballet flat + leather tote + leather strap watch

preppy aesthetic outfit

jeans | shirt | shoes | tote | watch

For true lovers of the preppy aesthetic, this next look can certainly be found in your closet! Starting with these slim wide-leg jeans, this look once again relies on truly classic wardrobe staples and mindful accessories for the real preppy effect.

On top, there is no going wrong with this oxford button-down shirt. When it comes to styling, there is really no unflattering way to wear this piece; tuck it in or leave it out, roll up the sleeves or leave it as is! 

This classic beige bag is a perfect accessory for this basic look, tying in with the two-toned ballet flats that tie the final aspects of the look together. Incorporate this black and gold watch into the look for an extra touch of black for an all-around elegant outfit you will keep coming back to over and over again. 

Entering the Fashion World of Preppy Aesthetic Outfits

Preppy fashion has dominated the fashion scene for years as a style that alone defines various brands – from high-end to affordable luxury – and is still a very coveted look today.

Chanel, Ralph Lauren, J.Crew, and Lacoste are great examples of the preppy aesthetic; though they all lean towards slightly different versions of this specific facet of fashion, these brands revolve around the same general style principles. The old money aesthetic, for example, incorporates many of the trademark preppy pieces into its own outfits and charm. 

And though television shows and movies might try to tell us differently (anybody watch Gossip Girl?), the preppy aesthetic definitely belongs beyond the confines of private schools, the Ivy League, and the country club!

This style can be truly adaptable, with looks ranging from a casual outfit to Princess Diana chic for formal occasions. The preppy aesthetic is a great option for those who like to be very intentional about their looks, as the right accessories can easily upgrade a preppy outfit and take it to the next level. 

To get started with this style, think about what aspects of the preppy style you really love: Is it sweater vests, a pleated skirt, or oxford shirts? Anything is possible when you know how to properly incorporate these versatile pieces into your favorite kinds of looks. Classic items will never go out of style, but experimenting with newer trends can also be a fun way of discovering even more about your personal style.

Like with any outfit, putting together a great preppy aesthetic look is about understanding the essence of the look, while still prioritizing your individual preferences and merging the two effectively.

At the end of the day, it’s important to remember that preppy doesn’t mean sacrificing your individuality, but instead, it’s about expressing yourself – with an extra dash of poise and confidence, too!

A cardigan is an essential piece of preppy aesthetic outfits. Want to know how to style one? Up Next: How To Wear a Cardigan: Style Tips for Every Occasion


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.