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Preppy style goes back years, it is a style that has been embraced by many for several decades, in fact. Think Princess Diana, or more recently TV icons like Blair Waldorf, played by Leighton Meester.

The style came into fashion in the 1950s but knew great success throughout the decades. Celebrities and TV shows have made us long for that preppy vibe – it’s classy but still girly and fun.

Inspired by the style of students at prep schools in the States, it has now become accessible to anyone outside of those circles. You don’t need to be part of a yacht club or own several beach houses and a private jet to enjoy the look – phew!

The whole mood consists of clean lines, classic cuts and timeless prints. Trend-led pieces are kept to a strict minimum and there is a touch of schoolgirl.

You will have a few investments pieces, and keep your trend-led items to a minimum. Preppy styling will save you a bit of money in the long run. You won’t grow bored of certain items and leave them unloved at the back of your wardrobe (been there!)

You will no longer regret your purchases, and wonder what on Earth you were thinking. If you loved tailored and structured pieces with a feminine twist, then this is the style for you!

The preppie look was big in the eighties, as evident on the runways and the big screens of the decade. 1980s preppy style is a fun fashion aesthetic to emulate in 2020, and we’ve found the best ways to “get the prep” today. 


Slacks or jeans, a pastel polo, and cardigan or sweater

Celebrity inspiration: in the 1980s, Calvin Klein was a huge name in the fashion world, with his jeans and briefs gracing the bodies of celebrities and the “normal” folk of the world. Some of his campaigns and collections had a distinct preppy vibe to counter the super-sexy underwear and toned bodies.

However, Ralph Lauren was and still is the ultimate preppy brand, with 1980s collections featuring bone-colored slacks, pastel polos, blazers, and boat shoes. The models were tanned and windswept beauties you imagine to be named Bunny and Chaunce off for a spot to have drinkies with Kitty and Chip. 

One of the most inspiring photos of 1980s preppy fashion shows Brooke Shields dressed in a pink polo, a yellow sweater over her shoulders, and high-waisted dark blue jeans. Her big, curly hair and sultry makeup made her the ultimate all-American girl. 

This look reminds us of days on the golf course, Summer barbeques, or strolling the grounds of a tree-lined university. In real life, it could be a great look for weekend markets, work casual Fridays, and afternoon drinks on the lawn. 

Preppy style is associated with the higher class, Ivy League universities, expensive prep schools, Hamptons holidays, spendy skiing vacations, and all-round clean aesthetics.

Think polo shirts, slacks, chinos, argyle sweaters, cardigans tied around the shoulders, knee-high socks, nautical stripes, crisp shirts, plaid skirts, and brogues. 


  • If polo shirts are just not for you, swap it out for a pastel or candy-colored crew-neck tee or cotton shirt tucked into dark blue kick-flare jeans
  • Pick a contrast-hue sweater or cardigan and tie around your shoulders 
  • Pair with black Chelsea boots under your boot-cut jeans, or smart white tennis shoes 
  • Edge-up the look by picking distressed skinny jeans and studded leather brogues worn with your sensible blouse and sweater (party on the bottom, preppy on the top)

Shirt-dress with cable-knit cardigan 

Celebrity inspiration: Reese Witherspoon’s timeless everyday style is classic preppy mixed with Southern glamour. Reese takes classic 80s-style preppiness and brings it into the modern era seamlessly. She rocks white jeans, tennis shorts, dark blue jeans and flats, all with her signature item: the preppy button-down shirt in crisp white or pale blue. 

She’s also a fan of the clean shirt dress, cinched at the waist and worn with flats or wedges. This is a sweet little ensemble for more casual workplaces, weekend markets and brunching, and hazy afternoon drinks. 

Reese is also often snapped with a tote slung over her arm, fresh hair, and minimal-yet-curated accessories such as sunglasses and a leather belt. Reese is our Southern-meets-California preppy queen. 


  • Find a denim or chambray shirt-dress with a hemline that sits above or below the knee (mid-knee-skimming hemlines tend to be unflattering) with a self-tie, or cinch with a braided tan belt
  • Pair your shirt dress with leather Chelsea boots or moto boots, or strappy wedges for Spring (and a little extra height)
  • Deconstruct the look by pairing an oversized bright white linen shirt dress with tanned suede Western-style boots and a tote over your shoulder 
  • Up-the-prep with a nautical-style striped sweater worn over your shirt dress with the shirt collar exposed, or with the sleeves tied jauntily round your neck


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Pastel Bermuda shorts with a cotton shirt, cardigan around the shoulders, and visor 

Celebrity inspiration: Emily Gilmore from ‘Gilmore Girls’ is the ultimate old-school preppy baby boomer. The senior Gilmore woman was most often seen in smart skirt suits or a gold-buttoned collarless jacket and neat slacks. 

However, on a few occasions she was seen in a more preppy-casual attire of bermuda shorts, a pastel shirt (tucked in), a cardigan worn around the shoulders, and a visor. 

This is the perfect outfit for a day on the golf course, touring college towns on foot, or running weekend errands. However, if you’re not living in a fancy fictional world, it’s a great costume idea for an 80s/90s preppy party. Or, adjust it to make it edgier and less refined for 2020 casual styling. 


  • Find a pair of high-waisted denim “skorts” or culottes and pair with a plain marle grey tee or graphic long-sleeved tee
  • Get your hands on some woven huarache flats for authentic 80s styling, or go full golf-course prep with plain white trainers or Keds
  • Search for a college-style cardigan or jacket with contrast trim on the lapel, cuffs, and pockets and sling it around your shoulders 

 Pleated miniskirt, sleeveless Argyle sweater, knee socks, and Keds

Celebrity inspiration: Rachel Green’s style on early season ‘Friends’ has become somewhat of a reference point for 2020 casual styling ideas. 

Her style had some overhangs from the 80s preppy scene mixed with 90s sweet-grunge, for example; shirts tied at the waist, mini skirts and cute shoes, and her USA long-sleeved top (OG fans will remember).

However, her most preppy look was a tartan pleated mini, knee-high socks, and a high-neck crop sweater.  

This is arguably one of Rach’s most iconic and recreated looks of the early seasons, and for good reason, she looked so darn cute! This is an ideal look for a Friends-themed costume party, or a 1980s preppy party. 


  • If you’re past your ultra-mini phase, opt for a tartan midi-skirt with a pencil silhouette and high waist and pair with a cropped long-sleeved boxy-style sweater
  • Pair an a-line miniskirt with an argyle sweater and shirt with the collar peeking over the sweater neckline
  • If you prefer full tights as opposed to socks, there are some great stockings on the market that feature a knee-high-style illusion with opacity to or over the knee, with sheerness at the thigh 

Country-chic with tan trousers, a crisp white shirt, and tweed blazer 

Celebrity inspiration: in the 1980s, Ralph Lauren was the ultimate preppy brand (and still is). Campaigns showed men in creamy-colored trousers, tan brogues, ties, and navy blazers, or all-white tennis outfits with shorts and polos. 

The women were dressed in tan trousers, tucked-in white shirts and tan belts. Or smart Ivy-style with trench coats, tweed blazers, neckties, and all-beige outfits.

The Ralph Lauren preppy look is fused with country, equestrian hints, with all-American overtones. You can easily translate this look into 2020, as it’s timelessly classy and very versatile.


  • Find a pair of cream or tan high-waisted, pleated trousers and wear with a tan leather belt and white linen blouse tucked in. Rough-up the look by rolling up the sleeves and unbuttoning the top few buttons for a low V effect 
  • Pair with a navy cardigan worn undone for casual wear, or an earthy-toned tweed or wool blazer 
  • Streamline the look by swapping out pleated trousers for slimline cream or tan denim jeans in a straight or boot-cut 
  • Swap out the blazer for a v-neck cable-knit or argyle sweater vest worn over a roomy linen blouse 
  • Tan or chocolate-brown Chelsea boots or tan leather brogues are a classic footwear choice for smartwear, or leather slip-on moccasins for a more casual (but still classy) ensemble 
  • For the true 80s Ralph Lauren preppy-country aesthetic, wear your hair out and lusciously lifted at the roots, with soft brown kohl on the eyes, deep nude lips, and a golden tan if your complexion allows 

Pretty in Pink

One of the key fabrics to rocking the preppy look is tweed. It’s timeless, looks pricey and adds structure to your look.

A tweed coat with a matching pair of high waist shorts makes your look appear put together with minimal effort just from the color coordination. The fabric looks expensive, notably because of its Chanel-esque roots.

Winter Prep

Style Caster - women wearing preppy winter outfit
Source: Style Caster

This outfit looks like something straight out of Gossip Girl. A longline military-style coat allows you to add a touch of androgyny all whilst remaining preppy. Another top tip to getting the preppy look is by layering – cute shirt collars underneath dresses will give a uniform vibe that we love! 

Sailor Style

One of the timeless prints you can opt for in your preppy wardrobe is stripes – nautical ones. Also known as the Breton stripe, it is a print that is always on trend and just magically goes with everything!

Choose dark stripes on a light background to make your skin glow and team with white straight leg jeans and boat shoes for a casual and chic look. A low bun will help keep the look low key but smart.

In the colder months, you could wear a striped jumper with a tweed skirt or with a white coat to keep it bright yet cozy.

Bold Plaid

The Atlantic Pacific. Women wearing bold plaid yellow outfit
Source: The Atlantic Pacific

If you want to take your preppy outfits to the next level, make them loud! This plaid tailored outfit reminds us of Clueless, but a modern-day version.

The simple black knit allows the suit to do the talking and teamed with similar toned accessories brings it down to Earth. If you really want to embrace the Clueless vibes this outfit gives, then wear your hair poker straight just like Cher would!

Equestrian Excellence

Though Blair was the Queen of Prep in Gossip Girl, Serena sure had some stunning looks too. She loved to play with different styles, but we have a little weak spot for her preppiest outfits.

We love this ensemble with a camel trench and Equestrian-style high boots that help bring that preppy touch.

Cute Collars

When refreshing your wardrobe, the piece that just has to be on your radar is a series of shirts with some seriously cute collars. Not just your basic short collar, but a Peter Pan collar, a scalloped collar, anything really unique.

This will help bring a statement to your most classic of outfits. Let your collar poke out over your favorite knitwear to not only keep warm but also make a statement. A pair of flats and you’ll be ready to go!

Skater Success

Though we love straight fit skirts, you should also get your hands on a skater skirt. It’s flirty, feminine and playful – it has to be on your list of essential pieces!

Its high waist cinches you in to create an amazing silhouette, and its flared fit elongates your legs. A simple white blouse will keep your look structured and classic. 

Mid-Season Marvel

Kiel James Patrick. Women wearing navy blazer, pink tweed skirt and white shirt
Source: Kiel James Patrick

Navy and pastel pink make quite the pairing! A baby pink plaid skirt is a chic addition to your wardrobe and screams preppy vibes. We particularly love scalloped hems, which make the skirt even girlier!

The navy military-style pea coat is the perfect finishing touch and goes perfectly with the hint of blue in the plaid.

Countryside Prep

Northern Preppy Girl on Tumblr
Source: Northern Preppy Girl on Tumblr

How to rock the preppy look in the countryside? A plaid skirt, cable knit and wellington boots make the perfect ensemble!

In fall and winter, we love seeing long socks peeking over boots, whether they are wellington, leather or ankle boots – it adds schoolgirl vibes, à la Blair Waldorf! In the colder months, we would wear a long line plaid blazer for a coordinated look!

Plaid Dress Dreams

Society 19. Women wearing navy coat and plaid dress with boots
Source: Society 19

Plaid – check, knee-high socks – check, pea coat – check and timeless tones – double check! Navy and burgundy are lusciously autumnal and chic. Layer a plaid pinafore dress over a collared shirt for sophistication at its best.

Opt for a simple shirt collar or even a pussy bow collar blouse for a retro touch. Get your knee-high socks at the ready and give yourself model-like legs. Stomp your ground and prepare to turn heads!


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Heritage Here

To rock that preppy look, there are so many prints you need to get your hands on! We mentioned plaid, but the heritage trend can add a British touch – herringbone and tartan will work magic on your wardrobe.

We love a hunter-style padded gilet with Equestrian boots and a simple black roll neck for a luxurious look. Keep your jewelry to a minimum with a simple gold chain and leather strap watch.

So Adorable

It’s all in the details – this adorable cropped cardigan is the perfect layering piece. In a delicate polka dot print and gold buttons, it is a strikingly chic cover up.

A pussy bow collar blouse, which will also be an ally in building a preppy wardrobe, finishes off the look beautifully. Keep the rest to a minimum – simple jewellery and nude accessories will allow your understated look to remain classy.

Parisian Prep

If you love Parisian fashion, then a beret will be your ally for battling the winter freeze – and it will save you from bad hair days! Team it with a cropped jacket with a scalloped collar for a hint of preppiness.

The plaid skater dress with pleats flatters your figure and the length is elegant and classy. A hint of orangey red lippie will elevate the look!

So Sixties

Margo and Me. Women wearing sixties style check coat
Source: Margo and Me

Another print to embrace in your capsule wardrobe is houndstooth. It adds a 60s’ touch to your look, and in tweed, you can’t go wrong!

A round collar allows you to show off the collar of your favourite pussybow blouse, and pearl earrings add a bit of glamour. Finish off the look with a luxury handbag to take your whole look to another level!

Cape Cover-Ups

A Clothes Horse. Women wearing a cream poncho with a skater skirt
Source: A Clothes Horse

Another must-have cover-up is the cape. In the lighter months, it can be thrown over your favorite cable knit and skater skirt, in the chillier months, it can be thrown over a military coat and pinafore dress.

Get yours in a range of timeless shades – neutral and pastel shades will be perfect for teaming with your favorite accessories.

Sweet Suede

Fashion Mumblr. Women wearing preppy fashion
Source: Fashion Mumblr

Simple neutral shades are the key to modernizing a preppy look. Your color scheme should remain simple. That isn’t to say monochrome is a must, but opt for navy, black, white, nude and natural tones that will not go out of style anytime soon.

The must-have blouse for any preppy lover is the pussy bow blouse. The suede skirt adds texture and adds a little edge.

Pinafore Party

If you want to modernize your tweed selection, a tweed pinafore dress is the piece to go for! What we love the most? Metallic thread within the tweed adding a little something extra.

Layer it over a black fitted roll neck to allow your dress to be the center of attention. Your knee-high boots can be traded in for Chelsea boots in warmer temperatures.

Finish off the look with a statement headband – a twisted-style will give a Victorian touch. Loose curls give an effortless finish to the whole look.

London Look

Mode and the City. Women wearing a check a-line skirt with brown sweater and tan handbag
Source: Mode and the City

Incorporate the heritage look into your outfits with a check a-line skirt. It’s wrap front like detail flatters your frame and adds movement to the skirt.

A thin knit is perfect for tucking into the skirt without any excess bulk, whilst the matching leather satchel crossbody wraps up the whole look.

A timeless beige trench is the ideal outerwear for someone testing out the preppy look.

Cool Cord

Want to make your preppy look a little more edgy? Change up your fabrics! A cord a-line skirt is perfect for the colder months.

Its vertical lines are slimming, and the fabric screams 80s vibes. A classic roll-neck and knee-high boots make the outfit classier and timeless.

Finish off the look with a check wool coat and a cute scrunchie, you won’t get enough of this outfit!

Pastel Paradise

Although pastel pink is the go-to pastel shade for preppy lovers far and wide, lilacs can also rejuvenate your look.

Opt for a pink tweed skirt and a lilac coat to balance out the colors, the white roll neck body creates a streamlined silhouette and the pearls are an elegant finishing touch. A pair of nude ankle boots will allow you to look put together and stylish!

Luxury Mix

In The Frow. Women wearing oversized sweater, Burberry printed scarf and brown mini skirt
Source: In The Frow

We are crazy for the color palette in this look – cream and beige are cool and classic whilst the iconic Burberry printed scarf brings a bit of glamour to the outfit.

The key to an expensive-looking wardrobe isn’t necessarily to splash the cash, but mix more bold and designer pieces with more affordable yet timeless items.

Who said you needed to be a millionaire to have a classy wardrobe?

Team Teal

A color that often gets neglected is teal. It’s a rich, wintery and classy color that will go with all of your wardrobe.

We love this teal coat with simple buttons which really brings out the elegance. Coupled with the perfect wool sweater with boot cut jeans keeping you warm and snug!

Check Mate

Kelly in the City. Women wearing a tartan long coat
Source: Kelly in the City

Last but not least, if casual is more your vibe, then incorporate a hint of preppiness with a check belted coat.

The coat will highlight your figure, and the check print makes it so easy to accessorize. Team it with an oversized roll neck knit or with your prettiest blouse for a versatile outfit.

About The Author

May is totally crazy about the 80s and everything the decade inspired! Having grown up in a household that was totally taken over by 80s music and fashion its only natural that May lives and breathes the 80s!

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