💘10 Chic Preppy Outfits for Everyday Elegance

preppy outfits

A woman with a preppy look appears classic, modern, and polished. Often associated with the East Coast elite aesthetic, this chic and elegant style has been refreshed over the years to become a fashion trend.

preppy outfits

If you were born in the 1990s, you’re likely familiar with Gossip Girl, a show known for showcasing the wardrobe of Manhattan’s privileged youth.

Pop culture influences fashion, inspiring the clothing choices of entire generations. In this article, we’ll explain what preppy style is and show you how to create a wardrobe that mirrors that of a true “it girl”!

The Origins of Preppy Style

This style originated in the 1970s. The term “preppy” is short for “preparatory schools”, referring to the prestigious and expensive private schools in the northeastern United States, such as those that feed into Ivy League institutions like Yale, Harvard, and Columbia.

preppy outfits

At these schools, students reimagined the traditional uniforms worn by their parents. These schools emphasized a British upper-class aesthetic, creating a culture of tradition with coats of arms, specific colors, and an overall feeling of belonging.

For boys: The uniform typically included a shirt, blazer, and school tie, paired with flannel pants or chinos and loafers or lace-up shoes.
For girls: The attire featured a blazer with a crest, a tartan skirt, knee-high socks, and a fitted cardigan.

preppy outfits

Today, preppy style represents not just clothing but a lifestyle symbolizing conservative values and high social status. Wearing this style reflects belonging to America’s financial and intellectual elite.

Key Elements of Preppy Style

At first glance, preppy style may seem simple, but it’s actually quite thoughtful and layered. You can play with layering, adding small touches like a crest to an existing blazer for a custom look.

Staple school-inspired pieces: Think aprons, knee-high socks, thick tights, cardigans worn over the shoulders, blazers with crests, loafers, or Oxfords.

preppy outfits


Logos: Whether small or oversized, preppy style emphasizes identification with visible logos and brands.


Classic yet youthful: There’s a fine line between classic and preppy, which always retains a fresh, youthful vibe.


Tailored fits: Choose structured pieces with clean cuts and quality materials.

preppy outfits


Layering is key: Pair a blouse with a V-neck cardigan, a long tailored coat, and a tweed skirt for a polished yet trendy look.


Sports-inspired pieces: Mix in items from high-end sports like tennis, golf, or polo—polo shirts, pleated skirts, tailored shorts, and bicolor shoes.

preppy outfits


A gender-neutral wardrobe: This style thrives on mix-and-match versatility.

Must-Have Preppy Pieces

Tops:

  • Classic Oxford shirts or pastel t-shirts with subtle stripes or modest prints.
  • Blouses with bow collars, oversized Peter Pan collars, or ties.
  • Polos.
  • Cardigans and cropped sweatshirts with embroidered crests.
  • Turtlenecks or round-neck sweaters for colder weather.
preppy outfits

Outerwear:

  • Blazers: Navy blue with gold buttons for a school uniform feel.
  • Trench coats: Neutral shades like beige or navy.
  • Straight-cut wool coats or plaid patterns.
  • Elegant capes, reminiscent of Audrey Hepburn’s era.
preppy outfits

Dresses:

  • Shirt dresses: Knee-length and sporty.
  • Apron dresses: Cotton or tweed versions depending on the season.
  • 1950s-style dresses for a retro touch.
preppy outfits

Bottoms:

  • Pleated skirts with tartan or checkered patterns.
  • Button-front skirts.
  • Flannel or chino pants.
  • Tailored shorts in tweed.
preppy outfits

Essential Accessories for Preppy Style

  • Hair accessories like bows or scarves.
  • Minimalist jewelry, including stud earrings and pearl necklaces.
  • Sunglasses, especially classic Wayfarer styles.
  • Long socks or loafers and ballet flats for footwear.
  • Statement bags like the Chanel 2.55 or Hermès “Kelly” and “Birkin” models.

Fabrics and Colors

Fabrics:
Opt for natural and luxurious materials that maintain structure:

  • Cotton.
  • Wool knits, tweeds, and flannels.
  • Tartan checks and fine stripes.

Colors:
Focus on neutral tones like white, beige, and navy.
Accent with bright touches, such as mustard yellow, emerald green, or royal blue, but avoid overdoing it.

Style Icons of Preppy Fashion

  • Princess Diana
  • Kate Middleton
  • Cher Horowitz from Clueless
  • Blake Lively and Leighton Meester in Gossip Girl
  • Gigi Hadid
preppy outfits

Preppy Brands to Know

  • Ralph Lauren
  • Tommy Hilfiger
  • Marc Jacobs
  • Lacoste
  • Gant

For a budget-friendly approach, thrift stores often carry unique pieces you can repurpose to create a preppy wardrobe!

Dos and Don’ts for Preppy Style

Do:

  • Customize existing pieces like adding a logo to your blazer or bomber jacket.
  • Keep the style minimalist and clean.

Don’t:

  • Avoid ripped or overly casual clothing—it’s the opposite of the polished preppy aesthetic.
  • Skip plunging necklines and ultra-short skirts.
  • Stay away from dark, moody colors that give a goth or rock vibe.
preppy outfits
preppy outfits

Frequently Asked Questions

How to achieve a preppy look?

  • Build your look around classics like blazers, V-neck sweaters, and button-up shirts.
  • Focus on clean lines and high-quality fabrics.
  • Incorporate minimal patterns like tartan or thin stripes.

What does preppy mean?
The term refers to the polished and elegant styles associated with American prep school students. It emphasizes comfort, quality, and recognizable brand elements.

Now you’re ready to wear preppy style with confidence!

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