17 Outfit Ideas to To Get That Preppy Style (Women’s Edition)

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Preppy styles are sometimes linked to more a more conservative or, shall I say, bland approach.

This is so not true.

It’s undeniable that a huge variety of 90s fashion is currently on the to-wear list of many women.

So, let’s get to grip with this iconic look.

A brief summary of the preppy style

The prep term represents a US subculture that dates far back from the 1920s. It originated in the university-preparatory schools of the country — “preparatory” being the keyword.

It comprised manners, words, ways of dressing, that translate a privileged lifestyle of the upper class. The preppy look has evolved throughout the decades, had a strong presence in the 60s, 80s, and 90s, and is making a modern come-back into the second decade of the 21st century.

This year, dress yourself in classy clothing, day and night, every season, casual occasions included. Read on to get the best tips to fall in love with and make your outfits feel new. The following guide provides plenty of styling ideas around must-have pieces, from head to toe, for your preppy fashion wardrobe. 

1. Bold head accessories on top

Back in the 90s, a big favourite for prep headgear was long slick hair. Nowadays you can go as wild as you want as long as you stick to the right combos. Below you can find different options to instantly upgrade your outfit. No more bad-hair days.

Show up in one of these:

  • Headbands can be worn with a ponytail, a braid, or loose hair. They come in bright colors, vivid prints, or are enriched with appliqués. To stay on the safe side, complement your look with a black satin one, for casual days play with the colors of your ensemble and if you feel more daring go for a leopard one. Animal prints are always on-trend, for festive evenings try bejeweled headbands.
  • Head bows, and bows in general. These are the details every preppy fashionista has reached out for. Add a head bow to a practical everyday look, working both as a contrast and to bring out your feminine side, or finalize your party dress with a perfect matching bow.

Set of 4 Headbands

2. Timeless pearl-jewellery everywhere

It’s impossible not to mention the queen of pearl ornament, Mademoiselle Coco Chanel, whose precious advice consists of mixing real pearls with fake ones! These spheres provide a magical dose of richness to any clothing and like Coco said:

Lace is one of the most wonderful imitations of nature. But pearls are perfect for every occasion.”

Coco Chanel

Under the preppy theme you can wear them separately or all at the same time, your look, your decision.

  • A strand of pearls, or a whole lot of them, can be easily combined with an evening gown or worn over a blouse or sweater to dress up your office days or get ready for a night out.
  • Pearl earrings are the little black dress of ear accessories, you and your outfit can never go wrong with a pair of these. 
  • A pearl bracelet, or a full-stack, is that lady charm that goes elegantly well with a pair of jeans, a day dress, or in simultaneous coordination of a necklace and earrings with a long dress to attend your finest party.

3. Sophisticated Outerwear

A good overcoat can truly wrap you up fashionably and be the statement piece of your entire outfit. By shopping for one of these staples you’ll balance your prep appearance. Dress it up or down, right before you leave the house.

  • The trench coat is a versatile item that can go on top of literally everything. It will look as stylish with a casual white tee and denim blue or black jeans, as it will work to tone down an evening printed or one-color dress. It was iconized by Audrey Hepburn while shooting Breakfast at Tiffany’s, and revisited by Leighton Meester in Gossip Girl, both shot in the big apple.
  • The cape coat has a more protective and prestigious character. Depending on the color and cut you choose, it can be the accent — if you go for the fierce leopard print — or the throwable comfort of your own style. Make it shine and wear it over a contrasting one color combo, play it down and match it with the same color as your top.

Cape Coat

4. Smart blazers

Thanks to Lady Di, the blazer is one of those memorable garments. It’s the go-to piece that makes your preppy look appropriately on and off duty. The oversized version of this piece grants the perfect balance for a smooth day to night transition.

Undeniably, Princess Diana was rightfully the preppy princess, who set uncountable trends that linger even today and keep reemerging on Katie and Meg’s wardrobe choices. Let’s see some royal examples:

  • Colorful options can add a posh tone (pun intended) to your day to day activities. The easiest way to get it right is to simply coordinate an all blacktop and bottom under it. You can go for an all white combo in warmer seasons as the attention stays in the blazer. You can pick whatever shade you want, Kate Middleton went for the exact same blue.
  • Checked blazers enhance a monochromatic look while ensuring an overall neat and cool feel. To dress like a duchess, reach out for a white top and black bottoms and you will be referencing Princess Diana and Duchess Meghan at the same time.

5. Clean-cut suits

This classic combination for the office, well known in the 70s and 80s as a power suit, got tweaked to its most feminine variation in the late 80s and 90s. The preppiest cut of the tailored ensembles arrived in new colors and designs, and went beyond traditional fabrics. The ultimate female formal staple became the skirt suit.

  • Plaid suits were popularised by the always mentionable Clueless movie. In a college setting, Cher Horowitz and her best friend Tai Fraser model two ways of styling this powerful pattern. The layering is the same, cardigan over a plain white tee. You can stick to canary yellow everything or pop in a red cardigan and match it with your lipstick.
  • Tweed suits were brought to the market by and carrying the brand name, the Chanel suit. This metallic and embellished lady-like offer became a sure alternative to the fashionable authority Anna Wintour.
  • This included exploring trims and cuts by pairing it endlessly for all sorts of events. To try this option skip the usual button-down and wear a plain basic top instead. You’ll be good to go to sit at any front-row fashion show. 

6. Cute and sweet sweaters 

Cozy does not need to be slouchy, and the preppy manner of bundling up proves it otherwise.

When looking for warmer pieces opt for fitted, thin sweaters and cardigans with some visual or texture component. It’s a key transitional item as it’s easily converted into dressed up or down occasions, and you can accessorize it accordingly.

Sweaters provide contrast a contrast combination of adequate feminity, on one hand, to ensure you’re properly covered. Yet on the other you can outline your bust with a close fit.

  • Fuzzy sweaters give a cuddly look and when worn directly over your skin bring a sense of sensuality just like Liv Tyler made it work in Empire Records. Wear it as a top over a skirt or jeans and keep all the other elements as neutral as possible.
  • Graphic motifs add extra sweetness to the prep girl. Taylor Swift shows it well, whether performing or spotted on the street, these cute sweaters are a must in her celebrity routine. Taylor highlights or uses the color blocking element for her looks. 

7. Collared shirts

A major preppy ambassador from the 90s was Rachel Green from Friends, and this particular way of layering a collared shirt under a fitted sweater is a clean outfit that revamps the classic button-down.

It’s a look that stays modern and is repeated by different celebrities, from Victoria Beckham to Julia Roberts who took it further and converted it into a full-dress — equally elegant respectively, when worn with tights and boots, as with bare legs and high heeled sandals.

  • Collared white button-down shirts are excellent pairings with a solid colour sweater and darker tones for skirts or pants, during winter and fall.
  • Polo shirts create a great and similar effect resulting in a more casual look, they are ideal for spring and summer. As these come in a wide palette of colors you can match it with bottoms and use the overlayer to play with the pop of brightness.

8. Chic women shirts

Chic shirts are a piece that comes in diverse options. They are all equally prep pleasing and of exceptional quality. The all-time favorite blouse.

Blouses remain the focus on the upper part of your body and closest to your face, a great opportunity to make it glow. This everyday essential, in either preppy pastels or bold tones, leaves room for creativity and adaptability depending on your mood or your agenda.

Make sure you have a few of these in your closet and counterbalance their feminine side with an opposite or approximate bottoms.

  • Reese Witherspoon, nominated actress for playing sorority girl in Legally Blonde, is an off-screen preppy lover, particularly of fancy shirts.
  • Lace and structured blouses can be taken less seriously when matched with a pair of jeans and flats. To stay formal grab a tailored skirt or black pants and hop on your high stilettos.
  • The same rules apply to lightweight blouses, in silk, chiffon or sheer materials that are coupled with skinny jeans or printed lady-looking skirts.

9. Classic stripes

Commonly associated with boat attire, stripes are effortlessly stylish and embody a mix of Parisian flair with a timeless character, this is probably the reason why they never go out of fashion.

This nautical garment print can be adapted to tops or bottoms, being the former the prime choice of countless personalities, men and women, across decades. An actress recognized and praised for her preppy outfits, and lately also for her lifestyle brand Goop, is Gwyneth Paltrow — who can never get enough of these lines.

  • Among the immense variety of look possibilities navigated by Gwyneth, the navy stripes are usually the focal point of her outfits and are better balanced with muted undertones.
  • The most relaxed approach matches striped tops with denim bottoms, shorts, and jeans if you want to make it casual smart throw a blazer on top!
  • A smart way of dressy stripes is to unashamedly assume you are a fan and opt for an overall mix, up and down, with a loose T-shirt and figure-hugging skirt to create a dress effect.

10. Skirts of proper lengths

To learn from the best, it is well worth revisiting — the unarguably preppiest First Lady — Jackie Kennedy and her quintessential colorful skirts. Using clothes in an official context requires not only protocol knowledge but a good amount of creativity to avoid overly safe boredom. See how Jackie played with high and low cuts, and how nowadays celebrities are adopting valuable style advice.

  • Pencil skirts are a figure-flattering choice, that work for all body types, privilege your hips, and can be coordinated in the same color separates like the many skirt sets of Jackie. Create a feminine two-tone ensemble like Angelina Jolie, quite perfect for office wear, and risk pulling off a more casual look by pairing a jersey grey pencil with a plain white tee.
  • Mini skirts were also present on Lady Kennedy’s fashions. An excellent combo that portrays simplicity elevated is a crisp white sweater tucked-in into a slick leather mini. A replicable and inspiring outfit that will make you stand out in-between seasons.

11. Khaki power pants

Highly associated with male fashion, this neutral shade of pants provides a sufficient amount of traditional class complemented with androgynous sophistication. A great reference for this matter is one of the most daring silver screen actress, Katherine Hepburn who used fashion as an expression tool.

Hepburn was a proud and public advocate of pants for women and this was back in the early 1930s when wearing trousers was not yet a given for females.

  • A laid back take on the khaki look involves wearing these pants as you would wear classic denim jeans. Select a basic white t-shirt and accessorize yourself with pearls to prove your preppy point.
  • Dress them up by trying the collared white shirt under a thin black cardigan — both must have items already mentioned above — and finish the look with feminine shoes like the staple black pump most women already have.

12. Elegant Dresses

A forever feminine item, regardless of your style, is an elegant dress. The charming preppy silhouette to pursuit is the one Grace Kelly fashioned in never-ending glamorous ways. The new look that won’t go out of style. You can opt for a more accentuated version for special occasions or a relaxed but still structured style.

  • The A-line dress that Grace wore in High Society combines the preppy blue pastel, the lightweight fabric, and the dreamy sleeves, no wonder she became a princess. A legacy clearly revisited by Keira Knightly.
  • The wrap dress remains in the memory of preppy fashion enthusiasts and is equally important for aristocratic strolls as it is for your summer getaway suitcase.

Don’t forget to rest your sweater over your shoulders — the preppy way of preventing a colder breeze!

13. Tie it all up with a belt

Keep your outfit safe with a multitude of belts to wrap around your waist over pants, skirts, dresses, or even coats! Typical preppy belts are a pop of color that highlights the line that divides your upper from your lower body. They can add more color, split two colors or purposely interrupt a one-color dress.

  • The skinny belt got picked multiple times for Sex and The City preppy-character Charlotte, who also took the accessory to enrich her personal outfits.
  • The ribbon belt tends to be a party feature and focuses on tiny waists. An easy way to create consistency with your accessories. Kim Kardashian got it preppy-right.

14. Preppy and sexy legs

The emblematic knee-high socks, and the encompassing reference to a school environment, show just enough legs while keeping them moderately warm. If the only thing that comes to your mind is that Britney Spears music video, fear not, Blake Lively has tested a multitude of looks that will get your fashion juices flowing.

  • Combining these with a skirt or shorts and a button-down or a feminine blouse will surely make an office statement. Colorwise you can go as loud or low as you feel like, see how great it looks in shades of grey with ultra-mini leather shorts.
  • For the grown-up version, dare to parade your inner femme fatal in an all-black outfit and long sleeve dress to make your legs shine!

15. Formally outlined legs

For colder days and lighter garments, you will need an item that ensures your warmth and style, or in this case an array of items, meaning tights. It all depends on how discreet or extravagant you want your look to be.

  • Colorful tights for festive and casual days. These can be the only way to fully color block your attire and brighten up your day, like Dianna Agron.
  • Neutral tones are great for day-to-day and formal events. These are the preferred choice of Olivia Palermo, the fashion influencer known for her elegant, unique, and always preppy street style who takes full advantage of this leg support. See how the opaque black ones can make your preppy A-line skirt bloom.

16. Polished shoes

This is an important detail if you really want to dress the preppy part, maintain your shoes clean and neat at all times. For superb comfort and parallel style try one of these:

  • Loafers, an item borrowed from the boys, are the daily companion for business meetings and casual dates. Explore leathers, buckles and other ornaments. Stay on the feminine side with skirts and dresses, or venture into a masculine look and evoke the lady within by tying a bow around your hair or around your neck.
  • Impeccably white sneakers bring the sporty element of a complete preppy education. This weekend preferred pair will boost your khaki pants when matched with a striped long or short sleeve.

17. Girly shoes

To walk preppy may seem challenging to manage, but rest assured that I have saved the best for last. The following shoe styles will not compromise your dancing moves, instead, they will upgrade all the above pieces to absolute can’t-fail preppy looks

  • Mary Jane pumps in all types and heights are the perfect fit for all seasons. Use them to unexpectedly transform a legging and oversized tuxedo look into an exquisite styling innovation — something to definitely try at home and then out.
  • Ballet flats gain a girlier vibe when paired with a dress, add dotted tights for extra girlie-ness. To acquire a sudden feminine urban feel match them with jeans, and bare ankles, great for an interview, even greater for the dance floor.

Wrapping it up

By now, you are hopefully feeling more knowledgeable about your preppy fashion abilities. Remember to mix and match the different pieces to create interesting looks. Create layers, mix prints and combine light items with neutral items to create balanced combinations.

One of the best things about having a preppy wardrobe is being able to play dress-up with different garments. Always stay confident, experiment, show off your good manners and have fun, you’ve got this!

Perhaps begin to gather some savings on the side to indulge in an occasional prep way of living — during your holiday or for spontaneous self-gifts.

Welcome the preppy new You!

Recommended: 90s Women, Now and Then