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15 Preppy Outfits To Channel Your Inner Gossip Girl

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Discover timeless preppy outfits for a classic and polished look straight out of the Upper East Side.

When we talk about preppy outfits, it’s impossible to not think of Blair Waldorf and Serena van der Woodsen – the iconic poster children of preppy outfits. In the world of Gossip Girl, it’s all expensive clothing – after all, private schools are exclusive, preppy, and chic.

But preppy fashion isn’t just reserved for the Upper East Side elite; it’s a timeless and versatile style that anyone can embrace. Whether you’re manifesting a future in the upper echelon of society, or simply want to change up your everyday look, preppy outfits offer the perfect blend of elegance and trend appeal.

When you’re ready to channel your inner Blair or Serena, these 15 preppy outfits are a great place to start.

The Cutest Preppy Outfits

1. Ruffled Collars + Plaid

A plaid skirt is a wardrobe essential if you love preppy outfits, as it adds a preppy touch to any look. In this chic outfit, the plaid mini skirt has been paired with a beige sweatshirt, with a little white ruffled collar pocking out the top. Finish with knee-high socks for a high school look.

Recreate This Look
White Misook Ruffle-Neck Stretch Cotton Blouse
Misook

Ruffle-Neck Stretch Cotton Blouse

At Neiman Marcus

Tan Departure Milano Crewneck
Departure

Milano Crewneck

At Revolve

Brown and black Steve Madden Jeanne Plaid Pleated Miniskirt
Steve Madden

Jeanne Plaid Pleated Miniskirt

At Nordstrom

2. Monochrome Color Palette

Stick to a monochrome color palette to create a stylish and sophisticated preppy outfit. This look pairs a black V-neck top with a black pleated skirt and a white tweed-style jacket. The all-black accessories, including the knee-high boots and black handbag, help to make the white jacket the statement piece of this outfit.

Recreate This Look
White and black LK Bennett Charlee Tweed Jacket
LK Bennett

Charlee Tweed Jacket

At Nordstrom

Black Amanda Uprichard Dixon Skort
Amanda Uprichard

Dixon Skort

At Revolve

Black Marc Fisher Lannie Knee High Boot
Marc Fisher

Lannie Knee High Boot

At Nordstrom

3. Cable Knits

Go for a cute and cozy preppy look with this cable knit and mini skirt outfit. The blue, chunky cable knit sweater looks stunning with the navy mini skirt, while the baseball cap, chunky socks, and Birkenstocks add a relaxed and casual touch.

Recreate This Look
Light blue Autumn Cashmere Cashmere Cable-Knit Crewneck Sweater
Autumn Cashmere

Cashmere Cable-Knit Crewneck Sweater

At Neiman Marcus

Dark blue American Needle New York Cotton Baseball Cap
American Needle

New York Cotton Baseball Cap

At Nordstrom

Taupe Birkenstock Boston Genuine Shearling Lined Clog
Birkenstock

Boston Genuine Shearling Lined Clog

At Nordstrom

4. Ivory + Black

Sometimes an outfit is all about how you style it, just like this ivory and black outfit with a sweater knotted over your shoulders, giving the look an instant preppy vibe. To recreate this outfit, you will need a white shirt, ivory smart pants, and sweater, then black accessories, including a black tote and black belt.

Recreate This Look
Ivory Treasure & Bond Oversize V-Neck Sweater
Treasure & Bond

Oversize V-Neck Sweater

At Nordstrom

Ivory Reformation Mason Pant
Reformation

Mason Pant

At Reformation

Black Saint Laurent Small Sac de Jour Leather Tote with Pouch
Saint Laurent

Small Sac de Jour Leather Tote

At Nordstrom

5. Sweatshirts + Pleated Skirt

We love this relaxed preppy outfit, that pairs a sweatshirt with a pleated skirt for a super cute look! This pale grey graphic sweatshirt adds a casual touch to the preppy pleated mini skirt, then you just need to finish the look with black loafers and a black shoulder bag.

Recreate This Look
Grey Departure Malibu Crewneck
Departure

Malibu Crewneck

At Revolve

Grey Noisy May Thea Pleated Miniskirt
Noisy May

Thea Pleated Miniskirt

At Nordstrom

Black Chanel Lambskin Quilted CC Turnlock Loafers
Chanel

Lambskin Quilted CC Turnlock Loafers

At Fashionphile

6. Tweed Jackets

Just add a tweed jacket to your outfit to give your look a preppy aesthetic! This pink and white tweed jacket is styled with a black mini skirt, white shirt, and impeccable accessories, including a chunky pearl necklace, a black ribbon at the collar of the shirt, and a bright pink bag – just gorgeous!

Recreate This Look
White and black Emporio Armani Pintuck Bow Tie Button-Down Shirt
Emporio Armani

Pintuck Bow Tie Button-Down Shirt

At Neiman Marcus

Pink and white Etro Check Bouclé Tweed Crop Jacket
Etro

Check Bouclé Tweed Crop Jacket

At Nordstrom

Black Norma Kamali Side Slit Mini Skirt
Norma Kamali

Side Slit Mini Skirt

At Revolve

7. Camel Cardigan

This camel cardigan preppy outfit is super easy to recreate at home and is the perfect weekend look! A soft camel cardigan adds a touch of color to the white shirt and white pleated skirt look. Add some cozy knee-high socks and knee-high boots to finish the outfit.

Recreate This Look
Camel Lulus Fall Fixation Light Brown Knit Button-Up Cardigan
Lulus

Fall Fixation Light Brown Knit Button-Up Cardigan

At Lulus

White Danzy x REVOLVE Tennis Skirt
Danzy

x REVOLVE Tennis Skirt

At Revolve

White Dirty Laundry Veelo Knee High Platform Boot
Dirty Laundry

Veelo Knee High Platform Boot

At Nordstrom

8. Pops of Red

Stick to a minimalist, neutral color palette then add a pop of color, like red, to create a striking outfit. The red boots and red bow in the hair add a fun pop of color to the neutral white skirt and grey oversized sweater look.

Recreate This Look
Grey Dries Van Noten Texas Wool-Blend Sweater
Dries Van Noten

Texas Wool-Blend Sweater

At Neiman Marcus

White Majorelle Zoe Mini Skirt
Majorelle

Zoe Mini Skirt

At Revolve

Red Kenneth Cole New York Lowell Knee High Boot
Kenneth Cole New York

Lowell Knee High Boot

At Nordstrom

9. Mini dresses

Style your mini dress with knee-high boots to create a stunning, preppy outfit. This black mini dress features a white scalloped collar, for an extra preppy touch, then is paired with patent boots, and a navy long wool coat to keep you warm during the fall and winter months.

Recreate This Look
Black and white Reformation Rocco Dress
Reformation

Rocco Dress

At Reformation

Navy Weekend Max Mara Resina Virgin Wool Coat
Weekend Max Mara

Resina Virgin Wool Coat

At Nordstrom

Black Saint Laurent Who Patent Block-Heel Knee Boots
Saint Laurent

Who Patent Block-Heel Knee Boots

At Neiman Marcus

10. Leather Skirts

Add an edge to your preppy outfit with this striking leather pleated skirt! The black leather skirt when styled with a blue button-down shirt and an oversized grey cardigan, perfectly fits the preppy brief but with a unique and edgy touch. Just add pointed-toe slingbacks and a black top-handle bag to complete the look.

Recreate This Look
Grey Helsa Sanna Cardigan
Helsa

Sanna Cardigan

At Revolve

Black Lulus Better Luck Next Time Black Vegan Leather Pleated Mini Skirt
Lulus

Better Luck Next Time Black Vegan Leather Pleated Mini Skirt

At Lulus

Black Jeffrey Campbell Persona Slingback Pump
Jeffrey Campbell

Persona Slingback Pump

At Nordstrom

11. Black + Navy

Black and navy is an underrated color combination that we just adore! Here, a navy sweater has been paired with a black pleated skirt, black knee-high boots, and a black leather handbag. The ruffled collar adds an extra preppy touch to this gorgeous outfit.

Recreate This Look
Navy Eleven Eleven Palm Tree Crew
Eleven Eleven

Palm Tree Crew

At Revolve

Black LoveShackFancy Ruffle Mini Skirt
LoveShakeFancy

Ruffle Mini Skirt

At Revolve

Black Chanel Lambskin Quilted Small Trendy CC Dual Handle Flap Bag
Chanel

Lambskin Quilted Trendy CC Dual Handle Flap Bag

At Fashionphile

12. Bright green

Don’t be afraid of vibrant colors within your preppy outfit, like this fun bright green tweed mini dress! This pinafore-style mini dress is styled with a white, balloon sleeve shirt to add a little drama and then finished with lots of gold jewelry for a glam touch.

Recreate This Look
Green Reformation Elva Dress
Reformation

Elva Dress

At Reformation

White Dice Kayek Puff-Sleeve Poplin Collared Shirt
Dice Kayek

Puff-Sleeve Poplin Collared Shirt

At Neiman Marcus

Gold Nordstrom Ginkgo Leaf Drop Earrings
Nordstrom

Ginkgo Leaf Drop Earrings

At Nordstrom

13. Shorts + Blazer

Keep it simple with this preppy black shorts and blazer outfit that looks super elegant and sophisticated. The black-on-black shorts and blazer are broken up with a white turtleneck sweater, then the outfit is completed with a black handbag, black sheer tights, and black sunglasses.

Recreate This Look
White Wolford Aurora Long-Sleeve Turtleneck Sweater
Wolford

Aurora Long-Sleeve Turtleneck Sweater

At Neiman Marcus

Black Reformation The Classic Relaxed Blazer
Reformation

The Classic Relaxed Blazer

At Reformation

Black Reformation Mason Short
Reformation

Mason Short

At Reformation

14. Black + Grey

A preppy black and grey outfit looks incredible during the fall and winter months – just like the outfit pictured above. Style your black pleated skirt with a black turtleneck sweater and layer a grey tweed jacket over the top to add a preppy touch. Finish off the look with black knee-high boots and a black shoulder bag.

Recreate This Look
Black Faherty Legend Rib Turtleneck Sweater
Faherty

Legend Rib Turtleneck Sweater

At Nordstrom

Black and grey Heartloom Billie Blazer
Heartloom

Billie Blazer

At Revolve

Black Alice + Olivia Carter Shiny Vegan Leather Pleated Mini Skirt
Alice + Olivia

Carter Shiny Vegan Leather Pleated Mini Skirt

At Neiman Marcus

15. Soft Knitwear

Layer your soft and comfy knitwear over pleated mini skirts when the weather starts to get a little cooler to create a cozy, preppy outfit. This grey mini skirt has been paired with a grey, oversized sweater, a white shirt, and white sneakers for a relaxed finish. The green handbag adds a pop of color to this neutral outfit.

Recreate This Look
Grey SER.O.YA Wool Devin Sweater
SER.O.YA

Wool Devin Sweater

At Revolve

Dark grey BP Pleated Tennis Skirt
BP.

Pleated Tennis Skirt

At Nordstrom

Green Sezane Claude Bag
Sezane

Claude Bag

At Sezane

Have you found your next outfit from this list? Let us know in the comments section! If you’re still looking for more fashion inspo, check the posts down below.

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