How to Wear a Pencil Skirt

So Jennifer Aniston, with her toned legs (ok, who are we kidding . . . her toned EVERYTHING), is basically the model of pencil skirt-wearing perfection. Not quite sporting the Aniston physique (not to mention bank account)

How to Wear Pencil Skirts

1. Choose the Right Length



Pencil skirts  come in three basic lengths- about two full thumb’s length above the knee, at the knee, and two full thumbs length below the knee. The best length in general is at your knee as that tends to be the smallest part of a woman’s leg- where ever the skirt ends is where the eye will travel or you could try this tip:

Simply, take a measuring tape to your shins (middle of knee cap to ankle bone) and note the number. Then, switch directions and measure from mid knee cap to your hip hone.

1. To find out your ideal skirt length, subtract the smaller number from the longer number.

2. Halve that number.

3. If your shins are shorter than your thighs, the number in #2 is the height above your knee that your skirt should hit. If your shins are longer than your thighs, drop the number length below your knee.

However, choosing the right length is also based on personal preference as well as particular situations. Here’s a quick guide.

For Work: At knee or below the knee
For Dates: Above the knee
For Church: At knee or below the knee
Over 50: At the knee or below the knee


2. Bottom Heavy? Go a Size Up and Get it Tailored.

pencil skirt

Pencil skirts on those who are bottom heavy tend to pull across the middle (from one side of your hip to the other), causing an unslightly  “whiskering/wrinkle” effect.  If you’re got a bit extra in the hip area, buy the skirt one full size larger and get it tailored to your body.


3. Pay Attention to Your Side


Most people pay attention to the way pencil skirts look from the front- which can be deceiving if you have a tummy or a pouch. When trying on pencil skirts, ALWAYS TURN TO THE SIDE, and see what the skirt looks like from the side view. If you notice a pouch, consider purchasing a size larger and get it tailored and/or make sure to wear a body shaper with the skirt.


4. Petite? Tuck it in. Tall? Leave It Out

pencil skirts tall long

If you’re petite, tucking the shirt in will make your legs look longer. If you’re tall, leaving the top out will make your torso look longer. The same rules apply to those who have long torsos (tuck it in to create a midline waist) or shorter torsos (where it out to create a longer waist, thus elongating your top portion).

5. Go For Color

colored pencil skirt


While black is the go to color for pencil skirts, we here at TBF feel that you should look into other color options like blue and red. A word of caution: if you’re bottom heavy steer away from colored pencil skirts unless you’re trying to accent your lower half.



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  1. says

    I really like the classic black pencil skirt with white top and belt featured.  I love pencil skirts because they can be worn for just about every occasion.  I’m all about being sexy, yet classy!

  2. says

    That floral pencil skirt is cayute!! Pencil skirts to me are cute with closed toe shoes. If the pencil skirt and top worn are solid colors I like to wear animal print pumps with. 

  3. says

    I love your blog and this post in particular. I mentioned it and linked to it in my latest post 12 easy and effective tips to make your legs look longer and skinnier. Check it out, hope you like it. Thanks again and keep up the good work.
    btw. can’t wait for your next post

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