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!

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.

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