How to Dress as a Preppy Girl? 31 Outfit Ideas & Styling Tips

Whenever we think of “preppy style”, two things automatically pop into our mind- private and prep school. The preppy style is a combination of these two. Private indicates all the rich and luxurious pieces, while prep is all about the formal touch and crisp and clean look. So, whenever we combine these two things, it’s a whole new style. Just for your information, preppy style isn’t just for these two groups but everyone alike. So, do not fear dressing up at all! It is a statement style, and anyone can carry it equally well.

The preppy style was very much in fashion till the nineties, and it was incredibly famous amongst the high schoolers. But then the pop and grunge took over, and preppy lost its shine somewhere. But not anymore; since the last few years, the world is going crazy over the preppy style once again. There are two main reasons for that- it gives a vintage vibe; secondly, it makes one look incredibly elegant and charming. It is a great style for all the boss ladies out there!

How to Dress Preppy?

The preppy style is a style one can never ignore! In our last post we talked about Preppy Hairstyles for Women, and today it’s all about preppy outfits. Preppiness is like a fashion statement that anyone can adopt regardless of their age, shape, and size. The key to rocking preppy style is to be confident in yourself. If you style up all gorgeous but don’t have the confidence to carry yourself or embrace your look in front of a crowd, it’s all going to waste. And you don’t want that. Well, worry not because we have your back. Whether you are into preppy fashion forever or are new and want to try your luck with a new appearance, this article is for you!

There is a constant misunderstanding of preps being snobs, which, judging by the costly attire and accessories they buy, is not surprising. However, this assumption can be very easy to attain if you are not careful about dressing. So how do you succeed in getting the preppy look without looking snobbish? What make-up style should you use? This article will cover the essential tips on dressing like a preppy girl, preppy style clothing ideas and creating your own pretty, snob-free, preppy look.

preppy outfits for girls

Styling Tips

Here are a few do’s and don’t’s of dressing up preppy. Make sure to keep these tips in mind if you want to rock your preppy look!

  • Ensure that your look is all formal. Don’t try to add a touch of casual unless you want to ruin your look.
  • The more colour-coordinated your outfit, the better!
  • Try to match your accessories with your outfit, especially the purse and shoes. Well, matching belts and hats are always a plus.
  • Try not to wear outfits above the knee length.
  • Keep your outfit as classy as possible, and refrain from adding a loud or funky touch.
  • Always tuck your shirt in, especially with a skirt or blazer pants.
  • Wear pantyhose with short dresses.
  • Refrain from wearing informal shoes and instead stick with boots or ballet flats.
  • Little accessories like a pearl necklace or studs are a must!
  • Remember the three C’s of preppy style- classy, clean, and crisp!
  • Your outfit must be well-fitted, neither baggy nor tight!
  • Never forget to do your hair with preppy outfits- ribbons, pearl clips, and printed headbands are the best options.
  • Colors sure do have a significant impact on everything. If you are all about preppy style, ensure you will have the right colours: blue, black, and white.

Must-Have Items

Creating a whole new wardrobe or adopting a contemporary style is never an easy job. Being a girl is hard enough because we need so many outfits, matching shoes, accessories, hairpins, and whatnot. Isn’t it true? Well, if you are a girl who wants to adopt the preppy style, you need to know that you’ll have to make an effort.

Begin with inspecting your closet and seeing what pieces you can use. Here we are about to provide you with a list of preppy style essentials. If you have them, that’s the best! But if you don’t look for similar pieces you can use them instead. If both of these ideas look flop to you, it’s time you go on a shopping spree. Remember that a bit of investment in your appearance or wardrobe will never go to waste.

Here is a list of preppy essentials for you all:

  • Leather tote bag
  • Whimsical dresses, skirts, formal suits
  • Pearl/diamond set
  • Headbands, scrunchies, ribbons (I highly recommend going through our guide on the Puffy Headband Trend)
  • Cashmere/fringe scarves
  • Nude long coats
  • Riding boots
  • Classic watch
  • Ballet flats
  • Striped sweaters/tops
  • Peachy-pink makeup pallet
How to Dress as Preppy Girl? 20 Cute Preppy Outfits Ideas


A preppy girl’s shoe rack will consist of simple footwear such as tennis sneakers, loafers, and moccasins. Brands such as Rainbow Sandals, Jack Rogers, and Sperry’s Top-Sider Boat Shoes are all a must for any wannabe prep. Topsiders are great as a summer shoe and, as any prep will know, are the perfect footwear when aboard daddy’s boat.

All preps have some nautical twist and will gladly show this in their clothing and footwear. Flat, classy oxfords are an excellent choice for preppy girls. They come in a range of colors and are brilliant for adding a sophisticated twist to any outfit?

How to Dress as Preppy Girl? 20 Cute Preppy Outfits Ideas


Perfectly groomed, clean hair and flawlessly applied make-up! Ideally, a good complexion to start with help as you will not need such a range of make-up items such as concealer and foundation. Apply makeup to clean skin as preppy girls have a huge thing about personal hygiene. Most make-up tones will include pastels and neutral colors.

These have a cute and intellectual look to them and do not come over as brash or cheap, which the preppy girl most definitely is not! Could you keep it simple?
Remember, preppy does not mean snobby. If you try too hard to gain the preppy image, you may come across as pretentious, and this is completely missing the point of the prep style.

How to Dress as Preppy Girl? 20 Cute Preppy Outfits Ideas


↓ 16 – Hairstyles

No preppy style look can ever be complete without the right preppy hairstyles. Whatever type of preppy outfit you are about to wear, remember that appropriate hairstyle is a must! You can go with hairstyles such as high ponytails, sleek bun, and neat curls.

Well, this alone can never be enough! You must wear pearl clips, headbands, scrunchies, and ribbons. Well, not all together, but one of them or two in any combination. A great tip is to match your hair accessories with the colour of your outfit.

Look Book


↓ 1 – Inspo for High Schoolers

The preppy style is a must for high school queens. If you are the all-girly person in your squad or who can’t stand the messy looks, we recommend you adopt the preppy style and let your charisma do all the magic on high school sweethearts. You can go with plaid and polka dot prints to look preppy yet fresh if you aren’t up for plain outfits.


↓ 2 – Tartans

Tartan is a favourite pattern choice for preppies, so it is not unusual to see a preppy girl rocking tartan skirts, jumpers, and knee-high socks. Make sure your tartan is matching, though. For example, do not wear a red tartan skirt and then wear blue tartan socks. This will destroy your preppy image, and the feel of being educated will go flying out the window.

The most commonly seen preppy skirt is the very versatile short pleated mini, and these do look stunning with knee-high socks and the right style of top to go with it. Why not find your perfect colour of tartan, which complements your complexion?


↓ 3 – For College Girls

Gone are the times when college girls were into grunge! These days girls want to look like boss ladies, all suited! If you are preparing for a business school, here is a look you can try out.

How to Dress as Preppy Girl? 20 Cute Preppy Outfits Ideas


↓ 4 – For Plus Size Women

Fashion brands play a significant role in making any trend go famous. There are many brands like Kate Spade, Ralph Lauren and J.Crew, Vineyard Vines known for designing preppy clothing. Here are a few plus size women acing the preppy style.

How to Dress as Preppy Girl? 20 Cute Preppy Outfits Ideas
How to Dress as Preppy Girl? 20 Cute Preppy Outfits Ideas

↓ 5 – For Teenagers

Teenagers are more into preppy style as compared to the prep or private schoolers! If you are a teenager who is into the preppy style, we recommend filling up your wardrobe with cute skirts and crip tops. Oh well, don’t forget to add ribbons to your ponytail.


↓ 6 – Preppy Pretty Royale High Outfit

How to Dress as Preppy Girl? 20 Cute Preppy Outfits Ideas

↓ 7 – Preppy Office Wear

The office is worn for the preppy woman- Great colour matches up with red and black—a collared shirt with a black jacket and a lovely black Louboutins with a matching bag. Collared shirts mostly require tying up your hair.

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And if you’re looking for more preppy workwear ideas, I recommend watching the Netflix series ‘Emily in Paris.’ Or go through our post on French Fashion Trends & Ways to Dress Like a French Girl.

preppy outfits

↓ 8 – Black and White Outfit

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↓ 9 – Oxford and Preppy

Oxfords are preppy girls’ best friends. So always invest in a good pair because they can be matched up with so many outfits these days.

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↓10 – Biker jacket with Polka Dot Top and Midi Skirt

What a fascinating way to wear your leather jacket and keeping everything else toned down to follow your inspiration and add the spice jazzed up with a blue skirt and black heels. Part rock anthem is what this outfit should be called for stylish girls.

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↓ 11 – Peplum top with Knee High Boots

Peplums are one of the super preppy clothing items so we highly recommend making them a part of your wardrobe. Here are more tips and ideas on Different ways to Wear Peplum Tops in Summers.

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↓ 12 –  Skirt With Chunky Heels

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↓ 13 – Plaid Style

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↓ 14 – Formal Look in a Preppy Suit

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#15. Polyvore

Winters are great for hiking or going on outdoor trips. To look super stylish and practical, wear long leather boots. A sleeveless vest with a tartan print shirt completes this sporty look.

15 winter preppy outfit ideas for women 1

# 16. Casual Day Out

For uptown girls who love to dress up, this look is for you! Wear a hot pink, bright sweater in order to shed your winter blues. A black and gold statement necklace with tweed pants help you look classy and elegant.

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#17. Burberry-Inspired Look

Try out this tan-brown Burberry coat with an off-white sweater for a chic, elegant, seductive look this winter. It is sure to turn heads!

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#18. For Teen Girls

Winters are not all about grays, blacks, or dull shades. Opt for a bright red scarf, a funky sweater, or a jacket with Dr. Martin shoes. So if you are looking for perfect preppy shoes for winter, it’s the best choice.

15 winter preppy outfit ideas for women 4

#19. Shopping Look

Shopping trips with friends mean dressing your best. Keep it casual with folded boyfriend jeans, black stiletto heels, and Ray-Ban sunglasses.

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#20. Daytime Look

Everyone loves to have fun in the sun during winter. Wear your brown Tory Burch handbag, elegant navy blue sweater, and crisp white pants for a sophisticated look.

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#21. For School/college

For college students, winters are all about staying warm. Choose an oversized warm woolen scarf with black leather pants and ankle-length boots.

15 winter preppy outfit ideas for women 7

#22. Working Moms Look

Professional moms need to look stylish, too, this winter season! Be practical with a white shirt, brown belt, camel-toned sweater and faded jeans.

15 winter preppy outfit ideas for women 8


23. Casual Look

For a quick, no-fuss look, grab your favorite coat and add a brightly colored cross-body handbag for extra style.

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#24. Get-Together With Friends Look

For a bright and funky look that is great for teens and girls in their 20s, opt for navy blue and red stripes. A brown tote handbag and gold accessories really stand out with this eclectic look. Rings look great with winter outfits. Take a look here at some really cool and trendy rings collection

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#25. Casual Style

For a romantic look, opt for a hat with a long blazer and a chiffon white blouse. Pair it off with a mini skirt and pleated handbag for the perfect winter outfit for the holidays.

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#26. Fall Outfit

For a truly preppy fall look, go all blue! Keep it furry with many fleece layers, and opt for knee-high boots. Super cute!

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#27. For School

Opting for a knitted zipped jacket with a Chanel handbag is this season’s most vogue winter look.

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#28. Work Wear

Here are some more cute winter outfits you can wear to work

15 winter preppy outfit ideas for women

#29. Date Night Outfit

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↓ 30 – Street Style Look

Who says street style look has to be a little rough? You can always walk down the streets looking all preppy! Here is a great street-style look that almost anyone can rock.

How to Dress as Preppy Girl? 20 Cute Preppy Outfits Ideas

↓ 31 – Celebrity Style

How can a person ever style well if there are no celebrities and famous people to get inspired from, right? We all see celebrities styled up all cute and elegant but little do we know the exact name of their statement style. If you are in this sort of confusion, here are the names of a few renowned people who are the preppiest.

  • Leighton Marissa Meester
  • Kate Midleton (Don’t miss out on these Kate Middleton Travel Outfits)
  • Jessica Biel
  • Jaime King
  • Jessica Alba
  • Katharine McPhee
How to Dress as Preppy Girl? 20 Cute Preppy Outfits Ideas


  1. Beatrice Hampton
    • Coach Ray James
    • Courtney Denise
      • Zoona
    • Olivia Davis
  2. Sara Auger
    • Olivia Davis
  3. Emme Yott
    • None
    • Olivia Davis

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