Style | Finding the Right Pencil Skirt


What is a pencil skirt? By definition, a pencil skirt is a very narrow, straight skirt that is slim fitting and generally falls to, or just below the knee.  It is named for its shape: long and slim just like a pencil. Pencil skirts can come in different cuts, lengths, styles, prints and colors.  To me – it seemed like my worst nightmare when I first encountered them…




Even though today they are one of my favorite articles of clothing – the pencil skirt was the first item that I gravitated towards when I decided that I need a more “adult-like” wardrobe. I didn’t want a full suit, but I wanted something that came across as structured, clean and professional.

I remember walking into an Express Clothing store and thinking to myself – how on earth do I wear this? What kind of shirt do I wear with it? Do I need tights? I wasn’t sure about any of those thoughts but I knew that I needed one – so I went with a basic black one and a color block one in black and white. (of which to this day, I still have) Little did I know that it was just the beginning of a beautiful friendship.


Today – most of the pencil skirts that I own are of solid colors that I can mix and match quickly on the go for the office. This one is a black high waist pencil skirt paired with my Kate Spade inspired sweater (details below). I am starting to build out my print options and I am excited to find some fun new ones this season.

Here are some tips to consider when wearing/purchasing a pencil skirt for work:

  1. Pay attention to the fit of the skirt. The skirt should be fitted around the waist and hips but not too tight. If you see horizontal lines forming across the hips – try going one size up instead. If you can insert one finger under the waistband comfortably, it is most likely the right fit. It you can insert two fingers under the waistband, or the skirt is sliding around on your hips it may be too large. *Consider getting it tailored if you love the skirt and its the only one left not in your size.
  2. Select the right length. A pencil skirt can be most flattering when the hem is around the knees. This will give you a slimmer look and also make your legs look longer. Going too high above the knee would not be appropriate for the office and going too long could ruin the overall shape of the skirt on your body. Test it out by sitting in the skirt. If your hips feel restricted, the skirt rides your thighs, or it does any bunching at all – leave it behind.
  3. To Tuck or not to tuck. If you choose to wear a high-waisted pencil skirt – i recommend tucking in your top. It adds a professional touch and creates a slimmer shape around the waist while elongating your legs. Untuck the top if you want to give off a more casual look or you would like to elongate your torso instead. If the shirt is a little more “blousy” or loose, try adding a belt to give your waist some definition.
  4. Add Texture. When the main frame of your outfit is complete (Skirt and top) be sure to add some texture, color, or accessories such as a bright shoe, a statement necklace or a fun bag to complement. It will add some dimension to your outfit and gives you the opportunity to showcase your style.





Pencil skirts are versatile and a fun option to have in your closet. Just by changing accessories or tops, you can make multiple outfits that scream YOU! Feel good and be sure to dress it up and down.

Thank you so much for stopping by and reading. I hope that I was able to inspire some new ideas for your pencil skirts or for you to try one on the next time you go shopping!

Jackie Signature

|Top: The Loft Bow Sweater, old (Similar here), DKNY Poncho, (Option Here)
|Bottoms: Express Pencil Skirt
|Shoes: Nine West Margot Pump
|Accessories: The Loft Bracelet Set, Similar Here (birthday gift), LIT Boutique Boston Bracelet

Author: Jackie

A marketing professional and lover of all things fashion and style, blogging on nights and weekends.

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