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Wednesday, April 16, 2025

How to Wear a Pencil Skirt

17 Ways to Style It

Master the pencil skirt look. Our style guide has all the tips and tricks for rocking this chic staple.

If you're looking to up your street style game, pencil skirts are a must. They add a touch of luxury to any outfit and can be styled in so many ways. Wearing a pencil skirt is all about making sure that your outfit is tailored to flatter your figure.

A pencil skirt can be a great addition to any wardrobe, but it can also be intimidating for those who are new to wearing them. If you're not exactly sure how to pull them off, don't worry. We've got everything you need to know about wearing pencil skirts.

MY Note: I love the pencil skirt even more than the dress.  Is it going mainstream for men?  Maybe some day, but not soon. The Jeans pencil skirt is my favorite and I only wish I could wear it more. Below are the bullet points from the article that each are good suggestions with an accompting photo. Well worth studying. 


  • Choose the Right Length
  • Go for a Flattering Fit
  • Know Your Shape
  • Consider Your Top
  • Accessorize with Care
  • Pay Attention to Your Side View
  • Start with the Right Undergarments
  • Petite? Tuck it in. Tall? Leave It Out
  • Go for Color
  • Pattern Play
  • Add Interest with Textures
  • Keep It Simple
  • Consider the Weather
  • Get Creative with Your Layering
  • Play with Proportions
  • Accessorize Wisely
  • (#17) Finish with the Right Shoes



#17 - The best way to finish off your pencil skirt outfits is with the right shoes. The type of shoes you wear with your pencil skirt can make or break your outfit.

Wearing the wrong shoes can make you look frumpy or careless, but choosing the right ones can elevate your look and make you appear more stylish and put-together.

As a general rule, you should avoid wearing flats with a pencil skirt. Instead, opt for heels or wedges. This will help lengthen your legs and make you look taller and leaner.

If you’re going for a more casual look, you can wear ballet flats or ankle boots.

And if you’re dressing up your pencil skirt for a night out, don’t be afraid to break out your stilettos. Just make sure you can walk in them comfortably!

With these guidelines in mind, you're ready to start shopping for pencil skirts. But before you do, keep reading for our top tips on how to wear a pencil skirt for any occasion.

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