Comfortable Pencil Skirt

Comfortable Pencil Skirt

I love a classic pencil skirt for its sleek silhouette but won’t tolerate things that bind. The traditional zip and hook waistband are no longer comfortable on my tummy so I appreciate designs with stretch. That doesn’t mean I’ll settle for a frumpy skirt which looks bulky and it doesn’t mean they don’t fit into my casual lifestyle.

Covered Perfectly recently added variety to their skirt line up and sent me two to share with you.

The first new print is a timeless Glen Plaid. It’s a traditional knee-length that looks polished for a work environment or can dress down for casual. You could easily roll the wide elastic waistband over to shorten it if you prefer to show more leg or want to wear it with black tights in the winter.Jennifer Connolly of A Well Styled Life wearing the Simple V from Covered Perfectly

I am wearing it with the Simple Comfort V-neck in white and a silk scarf. This top is a great chameleon and acts as a workhorse for your wardrobe.

Then they added a fun rose print over the Glen Plaid. The contrast of floral over a traditional menswear plaid shakes things up a bit. This skirt could easily dress up and take you out at night. Today I am showing it styled for a casual day of running around. Who says pencil skirts are only for work or getting dressed up?Jennifer Connolly of A Well Styled Life modeling rose glen plaid pencil shirt from Covered Perfectly

Jennifer Connolly of A Well Styled Life modeling rose glen plaid pencil shirt from Covered PerfectlyI’m wearing it with the Covered Perfectly scoop neck tank, some white Keds, a denim jacket and simple silver jewelry. These pull-on skirts are a great option for hot weather and go from casual to dressy with a quick change of shoes and accessories.Jennifer Connolly of A Well Styled Life modeling rose glen plaid pencil shirt from Covered Perfectly

Jennifer Connolly of A Well Styled Life modeling rose glen plaid pencil shirt from Covered PerfectlyThese skirts have infinite possibilities for a woman’s wardrobe and will go fast at their budget-friendly price.

A Well Styled Life readers receive a 20% discount on up to two items! Use the discount code AWSL when you check out at Covered Perfectly. The discount will apply on up to two items. Or you can take advantage of the buy 2 get 1 free, any combination.

Do you wear pencil skirts? Do you save them for dressier occasions?

Thanks for reading ladies and have a great day!


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  1. Susie
    May 10, 2018 / 5:27 am

    Pencil skirts are tricky at our age and can easily look a bit frumpy or fussy. However, I really like your second outfit as the white jacket/sandshoe combination give it an updated, modern look and I have recently worn a very similar look, but instead of sand shoes wore a pair of very soft, dull pewter open weave, lightweight lace-ups, called Rollies (they are big in Australia, but also sold in the USA. I think you look more relaxed and comfortable in the second outfit as well.

    • Jennifer
      May 10, 2018 / 6:23 am

      The second one fits my current lifestyle. I actually wore it that day to walk the dog, go grocery shopping and run errands. Very comfy.

  2. J'Laine Bradley
    May 10, 2018 / 6:41 am

    Love the second look!

  3. LA
    May 10, 2018 / 6:58 am

    THANK YOU for showing some skirts! I wear them all the time and they are a challenge to get right for the short, not-skinny person! Thanks for styling them; look forward to more!

    • Jennifer
      May 10, 2018 / 5:05 pm

      My pleasure. I love how cool they are so I will be styling more.

  4. Joanna
    May 10, 2018 / 7:25 am

    It’s strange but the first glen plaid looks fall/winter yet add the flower print over top and it fits into spring attire. The Glen plaid will look cute come fall with tights and booties. I do like the section nd version with the jean jacket and keds. It’s a versatile little skirt.

    • Jennifer
      May 10, 2018 / 5:06 pm

      The second look fits my lifestyle so I like it best too.

  5. May 10, 2018 / 10:37 am

    I also like your more casual second look better Jennifer – but the first look could easily be perfect for a more dressed up occasion. Thanks for working a skirt two different ways!

    • Jennifer
      May 10, 2018 / 5:07 pm

      It seems unanimous, the second look wins!

  6. L H Carter
    May 10, 2018 / 1:35 pm

    You are killing it with these 2 pencil skirts. Two great looks with black and white. WOW!

  7. May 10, 2018 / 3:55 pm

    You look great in a pencil skirt Jennifer. I have not worn one for years because I have narrow hips and that just do not suite me.

    • Jennifer
      May 10, 2018 / 5:08 pm

      Thanks Mollie. I have narrow hips too which is why I like them.

  8. May 10, 2018 / 4:48 pm

    Skirts are so good for summer. Both of your outfits are wonderful. I think I only own pencil skirts now…they always look good.

    • Jennifer
      May 10, 2018 / 5:09 pm

      You always look stunning in your pencil skirts!

  9. May 10, 2018 / 6:50 pm

    I love it when your posts inspire me to wear pieces from my own closet in new ways. I have a grey pencil skirt that is quite similar to the first one that you’ve shown here. It hasn’t seen the light of day in quite some time, but you’ve inspired me to pull it out and wear it again in a more casual way than in the past, similar to your second look here. Thank you!

  10. Allison
    May 10, 2018 / 10:00 pm

    The top look would work for me at work with black tights and black suede booties. I don’t do bare legs at work because at my age + varicose veins = not a good look. The second outfit would be a great weekend option though…

  11. Donna B Oliphint
    May 12, 2018 / 9:07 am

    Especially love the first look on you!

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