What Types of High Heels Go Best With a Plaid Skirt for a Preppy Outfit?

woman with high heels

Did you know that plaid skirts have been a staple in preppy fashion for decades? They are a timeless piece that exudes sophistication and style.

But when it comes to pairing them with high heels, the options can seem overwhelming. Fear not, for we are here to guide you through the world of footwear and help you find the perfect match for your plaid skirt.

From classic pumps to strappy sandals, Mary Jane heels to chunky block heels, and even ankle boots, we will explore the various styles that go best with a preppy outfit.

So, let’s dive right in and discover the ultimate combination of high heels and plaid skirts that will elevate your look to new heights.

Key Takeaways

  • Classic pumps and Mary Jane heels are a timeless choice that adds sophistication and elegance to a preppy outfit.
  • Strappy sandals provide comfort and versatility, allowing for different occasions and styles with a plaid skirt.
  • Chunky block heels offer stability and support, making them a comfortable choice for casual or dressy looks with a plaid skirt.
  • Ankle boots are a versatile and stylish option that complements a preppy aesthetic, with sleek designs that go well with a plaid skirt.

Classic Pumps

Classic pumps are a timeless footwear choice that instantly elevates any preppy outfit. These shoes are the epitome of sophistication and elegance, making them a perfect addition to any fashion-forward individual’s wardrobe. With their sleek design and high heel, classic pumps exude confidence and style, adding a touch of glamour to any ensemble.

What sets classic pumps apart from other shoe styles is their versatility. They can effortlessly transition from day to night, making them a practical choice for those who desire innovation in their fashion choices. Whether you’re attending a formal event or going out for a casual lunch, classic pumps will always be a reliable option.

Furthermore, classic pumps come in a variety of colors and materials, allowing you to experiment and create unique looks. From patent leather to suede, there’s a pump to suit every taste and occasion. For a preppy outfit, opt for classic pumps in neutral tones like black, nude, or navy. These colors will complement the timeless and polished aesthetic of your ensemble.

Strappy Sandals

When it comes to adding a touch of femininity and versatility to your preppy outfit, strappy sandals are a must-have. These stylish shoes not only elevate your look but also offer a range of options to suit your personal style.

Here are three reasons why strappy sandals are the perfect choice for your plaid skirt ensemble:

  • Comfort: Strappy sandals are designed with comfort in mind. With their adjustable straps and cushioned soles, they provide a snug fit that allows you to walk with ease and confidence. Whether you’re strolling around campus or attending a summer soirée, these sandals will keep your feet happy all day long.
  • Versatility: Strappy sandals come in various designs, from minimalist to embellished styles, making them a versatile choice for any occasion. Pair them with a plaid skirt and a crisp white shirt for a chic and sophisticated look. Alternatively, dress them down with a casual tee and denim jacket for a more laid-back vibe. The possibilities are endless.
  • Fashion-forward: Strappy sandals are a fashion-forward choice that adds a modern twist to your preppy outfit. Experiment with different colors, textures, and heel heights to create a unique and on-trend look. Opt for metallic straps or bold prints to make a statement, or go for neutral tones for a timeless and elegant appeal.

Mary Jane Heels

We absolutely adore the timeless elegance and feminine charm that Mary Jane heels bring to any preppy outfit. These classic heels are the perfect combination of sophistication and playfulness, making them an ideal choice for a plaid skirt ensemble. Whether you’re going for a chic and polished look or a more casual and effortless vibe, Mary Jane heels can effortlessly elevate your style.

To help you choose the best Mary Jane heels for your preppy outfit, we’ve created a table that showcases different styles and their unique features:

No matter which style you choose, Mary Jane heels are a must-have for any fashion-forward individual who wants to add a touch of class and sophistication to their preppy outfit.

Chunky Block Heels

For a stylish and comfortable addition to your preppy outfit, consider opting for chunky block heels. These trendy heels not only provide a fashion-forward look but also offer stability and support for those long days on your feet.

Here are three reasons why chunky block heels are the perfect choice for your plaid skirt ensemble:

  • Versatility: Chunky block heels come in a variety of styles, from ankle boots to sandals, allowing you to find the perfect pair to complement your plaid skirt. Whether you prefer a casual or dressy look, there’s a chunky block heel that will suit your style.
  • Comfort: Unlike stilettos or kitten heels, chunky block heels provide a wider base for your feet, offering better stability and reducing the strain on your arches. With added cushioning and support, you can confidently strut your stuff all day long without sacrificing comfort.
  • On-trend: Chunky block heels have become a popular choice among fashion-forward individuals who value both style and comfort. These heels are a modern twist on the classic high heel, making them a perfect choice for those who desire innovation and want to stay ahead of the fashion curve.

woman with high heels

Ankle Boots

Continuing our exploration of trendy and comfortable footwear options, let’s now turn our attention to ankle boots as the next stylish addition to your preppy outfit.

Ankle boots have become a popular choice among fashion-forward individuals who desire innovation in their wardrobe. These versatile boots offer a perfect blend of style and functionality.

Ankle boots come in various styles, allowing you to find the perfect pair to complement your plaid skirt. For a preppy look, opt for ankle boots with a sleek and polished design. Look for styles with clean lines and minimal embellishments. Classic black or brown leather ankle boots are timeless options that will effortlessly elevate your outfit.

To add a touch of playfulness to your preppy ensemble, consider ankle boots in unique colors or patterns. Animal prints, such as leopard or snakeskin, can add a bold statement to your outfit. For a more subtle twist, try ankle boots in rich jewel tones like emerald or deep burgundy.

When it comes to the heel height, choose what makes you feel comfortable and confident. Ankle boots with a low block heel can provide stability while still being stylish. If you prefer a bit of height, opt for ankle boots with a higher block heel. This will elongate your legs and add a sophisticated touch to your look.


In conclusion, when styling a preppy outfit with a plaid skirt, there are various types of high heels that can complement the look.

For example, a pair of classic pumps in a neutral color like black or nude can add elegance and sophistication to the ensemble. Whether you’re attending a brunch or a business meeting, these heels will surely elevate your style and make you feel confident and fashionable.

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