Master Modern Preppy Style in 2023: A Guide to Preppy Fashion Trends

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As we find ourselves in 2023, the modern preppy aesthetic has captured the fashion world’s attention, blending classic elements with contemporary flair. Gone are the days when preppy style was limited to those attending Ivy League schools. Today, this versatile and fashionable trend has gained widespread popularity, thanks in part to celebrity influence and designer interpretations.

Journey with us as we explore the essential pieces, styling tips, and versatile adaptations of modern preppy fashion.

To explore the opposite, retro preppy style, check out my article about it here.

The Rise of Modern Preppy Style

The roots of preppy trace back to the 1950s. These roots came from British college rowing clubs on the East Coast of the United States. As the style made its way through the halls of Ivy League colleges, it became synonymous with the upper class and American style.

Fast forward to the present, and the modern preppy aesthetic has experienced a resurgence in recent seasons. It evolved to incorporate urban influences and maximalist designs by brands like Noah and Gucci.

Key players in the rise of preppy style include iconic brands such as Tommy Hilfiger, Ralph Lauren, and Brooks Brothers. They each contribute to the popularization of this classic look. From pleated skirts and collared shirts to rugby shirts and tweed blazers, these brands have helped shape the modern preppy aesthetic we know and love today.

Essential Pieces for a Modern Preppy Wardrobe

At the heart of any modern preppy wardrobe lie essential pieces that, when combined, create the unmistakable preppy aesthetic. Some key items include:

  • Pleated skirts
  • Chinos
  • Khaki pants
  • Blouses
  • Polo shirts
  • Oxford shirts
  • Blazers
  • Sweater vests
  • Elegant sweaters

These pieces offer a variety of options for both men and women. You can incorporate those preppy essentials with contemporary items to achieve the modern preppy style. Items of contemporary styles include:

  • Hoodies
  • Statment sweaters
  • T-shirts
  • Linen shirts
  • Jeans
  • Smart Pants
  • Tennis skirts
  • Leather jackets

As you will see in the following outfit suggestions, these items offer a great way to incorporate trendier items into the timeless preppy style.

4 Modern preppy outfits

Now, let’s look at some modern preppy combinations!

Careless Jeans look

This combination of an elegant sweater and an Oxford shirt with a sweater above is rounded up by some classic blue jeans. By incorporating the jeans into the outfit, it gets a casual touch compared to the otherwise rather formal appearance. To fine-tune, some elegant sneakers or Pumps will look great on this outfit.

For more jeans combinations with preppy style, check out my article about 7 preppy jeans outfits.

Tennis skirt combination

For a modern approach on a sporty preppy style, the combination of a tennis skirt and a hoodie or sweater will look great. Additionally, you can add a polo shirt underneath the sweater to add a classic preppy touch to this casual outfit. To round it up, some sneakers and a little bracelet will look great.

The unicolored look

The unicolored look can consist of a combination of many preppy and contemporary items that all have one thing in common: The same color. Whilst some outfits may look great following the strict uncoloured approach, others may want to add similar colors that are not exactly the same for a more versatile approach.

Linen shirt summer outfit

Especially for summer, the combination of a linen shirt and some shorts will give off a unique modern preppy outfit. By switching up the classic Oxford shirt for a loose and flowy linen shirt, you will achieve a timeless but also trendy look.

Styling Tips for Modern Preppy Outfits

The key to nailing the perfect modern preppy look lies in mastering the art of styling. From mixing patterns and textures to layering and accessorizing, these tips and tricks will help you create unique and eye-catching ensembles that showcase your personal style while staying true to the preppy aesthetic.

For a deep dive into preppy accessories and ways to style them, check out my article here.

Mixing Patterns and Textures

Experimenting with different patterns and textures is a great way to create a unique and visually interesting preppy ensemble. Don’t be afraid to pair a striped rugby shirt with a plaid skirt or a floral dress with a textured cardigan.

When mixing patterns and textures, be sure to consider the colors, shapes, and sizes of the patterns, as well as the overall aesthetic of the outfit. Balance is key when combining different elements, so be mindful of the overall harmony of your ensemble to achieve a stylish and cohesive result.

Layering Techniques

A balanced and stylish preppy outfit requires mastery in the art of layering. When layering clothing, consider the colors, textures, and patterns of the pieces being combined, as well as the fit of the items and the overall balance of the outfit.

Layering can also help you maintain a comfortable temperature in both the winter and summer months. Opt for lightweight fabrics, such as cotton and linen, for layering in the summer, while heavier fabrics, like wool and flannel, are ideal for winter layering.


A well-chosen accessory provides the perfect finishing touch to any modern preppy look. Pearls, headbands, and structured satchels are all essential components for achieving a contemporary preppy appearance. Pearls, in particular, are a classic accessory that can elevate any outfit and add a touch of sophistication.

When accessorizing, consider how each piece complements your outfit and contributes to the overall preppy aesthetic. Also, you may want to incorporate some timeless shoes that will not take the main stage in your outfit but rather complement it. Some examples are:

  • Loafers
  • Boat Shoes
  • Elegant Sneakers
  • Pumps
  • Ballet Flats
  • Boots

For a more in-depth view on preppy shoes, you may want to read this article.

Final thoughts on the modern preppy style

From its origins in Ivy League schools to its resurgence in contemporary fashion, the modern preppy aesthetic has continued to evolve and captivate the fashion world. By incorporating essential pieces, mastering styling techniques, and embracing inclusivity and diversity, you can create a preppy wardrobe that is both timeless and fashionable.

Whether dressing for casual, workwear, or formal occasions, the versatile and adaptable nature of preppy style ensures that you will always look and feel your best, no matter where life takes you.

Frequently Asked Questions

Is preppy still in style 2023?

Preppy style is back and ready for some 2023 updates, with updated collared shirts and plaid skirts paired with combat boots, headbands, and ballet flats. It’s still very much in style.

What is current preppy style?

Current preppy style is characterized by oversized blazers cinched atop stirrup leggings, crewneck pullovers layered over button-downs, and varsity sweatshirts paired with loafers. Other items include polo shirts, cardigans, tweed blazers, collared tops, Breton tops, sailor shorts, a-line skirts, chinos, shift dresses, scalloped hems, boat shoes, and loafers.

What are the essential components for a modern preppy wardrobe?

A modern preppy wardrobe consists of pleated skirts, tailored pants, oversized blazers, and sweater vests.

How can I achieve a casual preppy look?

Achieve a casual preppy look by pairing classic pieces, such as polo shirts and blazers, with more relaxed items like jeans and sneakers. Mix and match colors and patterns to create a unique look that is all your own.

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