The High Waisted Pencil Skirt: How To Wear It Everyday

The high waisted pencil skirt is one of the unmissable basics in a woman’s wardrobe. I bet you have a form-fitted skirt in your closet, I bet it’s black, and I bet that you pair it with a white shirt 80% of the time. But what about being more playful, and start to wear it everyday?

Here’s 26 outfit ideas to style your pencil skirt, a ton of styling tips and some shopping suggestions to bookmark for when you decide to refresh your wardrobe!

The “Bon Ton” Style: Pencil Skirt + Tucked Top

Styling a pencil skirt with the top tucked in is one of the best alternatives you have if you want a simple and stylish outfit that doesn’t look too obvious. Plus, it’s a great choice if you want to enhance your body shape and look taller.

Here’s how:

  • When you tuck a top right at the waist level, it makes your legs look longer, so your figure is re-proportioned to look longer and slimmer.
  • When the waistband is thick, it will also keep your stomach tucked in together with the top, taking off inches from your waistline.
  • If you are petite, or have a short bust, consider keeping a similar shade for the top and bottom of your outfit, so your figure looks balanced. The leather high waisted pencil skirt in the outfits above is a good example!
  • On the other hand, if you feel your bust is too long, tuck in a top in a contrasting hue, and it will look a bit shorter.

But what if you can’t decide on what kind of top you should tuck in?

In that case, just use this simple rule: the thinner, the better!

So while you can wear just like every kind of top on your pencil skirt, make sure the fabric isn’t too thick so you can stay comfy and the top will be seamlessly tucked in.

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The Easy Style: High Waisted Pencil Skirt + Loose or Untucked Top

There are many ways of wearing a pencil skirt with an untucked top, and every  time you’ll get a different mood

  • If you love structured and flattering tops, you can opt for a bold look wearing a peplum top. Pairing it with a high waisted pencil skirt will keep an accent on the waistline, but at the same time, it minimizes big hips.
  • A simple t-shirt on a tight pencil skirt is  one of the trending model off-duty outfits. And in fact, it makes the classic pencil skirt + high heels outfit look more relaxed and easy.
  • Are you looking for a cushy and cozy outfit? Then just pair any pencil skirt with a big cozy sweater and you’re done. For how comfy this look seems, it’s also very flattering and gives you a fresh twist. My only suggestion here is just to wear it with heels, to avoid looking like a penguin because of the cloth volume on the top of your body!
  • A preppy outfit is another great mood to get with a high waisted pencil skirt and untucked top. Just make sure you wear a soft cardigan and make it interesting adding a shirt or some funny accessories, like bold necklaces, bracelets or just a cool bag.


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The Sprint Style: High Waisted Pencil Skirt + Flats

Flats are everything in spring and summer, that’s why they look great with colored outfits and bare legs.

Here’s some stylish ways to wear flats and athletic shoes under a pencil skirt:

  • Preppy and prints: a printed high waisted pencil skirt with a simple top and a pair of sandals or ballerinas, immediately make a mood without the need of adding accessories, makeup and all the rest. That’s the perfect style for those days when you wanna look put together without much effort. Just one side-note. When you opt for flats pay attention to the hemline of your skirt and keep it a bit above the knee, or you’ll look too old fashioned.
  • Sneakers and running shoes? Hell yes! Because if you know how to style them, they look good even under a gown. Here’s the secret: try to make them coherent with the rest of the outfit, at least for one thing. It might be a color accent or a sporty twist you add with other accessories, whatever that makes understand you didn’t just grab the first things in your wardrobe!
  • Fashionably preppy: my colleague Rachel Parcell is the specialist in this field, she’s always preppy and romantic, even when she wears sweatpants. To get her fashionably preppy look in your high waisted pencil skirt ( last picture) opt for pastel colors, flats and statement accessories like her pearls and her flat bag.

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How To Style The High Waisted Pencil Skirt at Work

The styling literature talks clearly about what to wear for work:

If thou wear a pencil skirt at work, thou-shall-not wear it in bold colors.

That means thou shall wear neutral colors. Hint: camel, pastels, black, blue, greys, browns.. And basically everything that doesn’t highlight your figure form the other side of the street.

Here’s how to style your high waisted pencil skirt to look cool at work:

  • Pastels on pastels: like wearing a camel pencil skirt with a white or other pastel tucked-in cardigan, neutral pumps, and a pastel coat. It’s the kind effortlessly fashionable style that lets you make a fashion statement without looking a fashion addicted.
  • Color blocks: If you like bright colors you can wear them at work, just put them on the right side of your outfit. On the top half of your body. A good example is a neutral pencil skirt + pumps, neutral accessories like bag and jewels, and a bright sweater with a shirt. No brainer, perfectly put together.
  • Monochrome: wearing just one color at work is so obvious and boring. Given that you only wear dark suits and combinations. But what about going monochrome with a softer color that compliments your skin tone? Just make sure you chose the right fabrics and the right fits to look well groomed.
  • Classic with a twist: what about a discreet print? It might be a black high waisted pencil skirt + a polka dots shirt, or a delicate herringbone fabric or print for  the skirt with a neutral shirt.

Whichever style you chose to wear at work, always try to keep your top tucked in,  so you look more put together. The only exception is if you opt for a preppy style, which is also work appropriate given that you stay balanced with the accessories!

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High Waisted Pencil Skirt: How To Style Prints

Wearing a printed pencil skirt is not as hard as it might seem at first, in fact you’ll just need to pair colors and fabrics!

Here’s some major tips to style a printed pencil skirt and look stunning:

  • If you want to look stylish and elegant, opt for non-stretch fabrics and classic cuts. Personally, I really don’t like prints on bodycon clothes, they make everything stand out too much, and I find those outfits too much sexualized. On the other hand, any printed pencil skirt with a straight or shaped cut is welcome to make you look and feel good.
  • Depending on your body shape, opt for the print size that best suits your measures, read this post to find out the right print size for you.
  • Pick the right colors: to style a great outfit from a printed pencil skirt, pick the basic color of the skirt and use it for the top and shoes, then choose an accent color in the print to add statement accessories, like bag or colored gems. That’s a surefire way to look incredibly stylish.
  • Mixing fabrics: if your high waisted pencil skirt has a light blue shade in its print, why not adding a thin denim shirt in the same hue? That’s the typical twist you want to have if you’re off-duty, enjoying a hardcore shopping session!

… Shop The Look…



Cover Credits 📸 Eleonora Carisi


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  • Great post!

    • Thank you Erika! 🙂

  • Oh Anna! You broke down the styles and tips so easily that I am excited to start wearing my pencil skirts after wearing so many seasons of midi and skater skirts!

    Thanks and much love,

    • Thank you Everest! I love your comment, because that’s exactly the message that I wanted to give with this post. Everything is wearable on a daily basis if you know how to style it! 😉

  • Love the pencil skirt inspiration! I need to wear more pencil skirts 🙂

    • Glad to hear that Akaleistar! 🙂

  • such a classic style that is so easy to refresh!


    • Definitely Kali! 🙂

  • Kelly H

    You’ve SAVED me- thank you. This has been the most challenging piece to pull out of my closet cause I do NOT get how to wear it! That’s all history!

    • Wow, these are the comments that make my writing effort feel really worth! Thank you Kelly, hope to read more from you, amend please let me know if you need more styling suggestions for your closet!


  • Jaye