How to Style // A Stretchy Pencil Skirt

October 7, 2013


I rarely find myself needing to dress in traditional office-appropriate gear, but recently I’ve fallen in love with these stretchy pencil-style skirts that seem to have shoved their more restrictive counterparts out of the way.  I have a quirky striped version, a classic solid navy, and one in animal print (naturally), and you’ve probably noticed that they’ve all found a welcome home in my closet over the past few months.

Back in the Spring, I was so flattered to be asked to style up a “3 Ways to Wear It” feature for Emma Magazine, and I knew immediately that this would be the item from my closet that I wanted to frame the piece around.

Keep reading to see how I created multiple looks around my latest closet staple, and shop the post to get the look for yourself!


This first look was definitely intended to provide a more professional take on the trend, and for my (imaginary) office outfit, I paired the skirt with a vintage structured top, statement bib necklace, envelope clutch & classic tan pumps.



Next, I wanted to include a look, that would be perfect for a romantic night out (might have to recreate this one for our next Date Night!), and I used a feminine embellished shell, a bright cardigan, while keeping the accessories simple with a geometric cuff and chunky blue heels (shown in the top pic).



Lastly (and my favorite!) – I needed to show how I like to wear the look most, and that’s for a casual day-date with friends or even just running errands around town.  I went for some major pattern-mixing by pairing it with a watercolor floral top, my favorite everyday handbag, aviator sunnies & the usual giant stack of bangles.



Photos by Michelle Herrick // Spread originally featured in Emma Magazine

Now I’d love to know: Which look above is your favorite?

Shop the post here…


Need even more stretchy skirt inspiration?  Check out the very same piece seen above from this post earlier this summer!

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  • Reply Rachelle October 7, 2013 at 8:21 am

    You look so pretty, love the different ways you styled the skirt.

  • Reply Jess October 7, 2013 at 9:09 am

    I love that skirt and every way you’ve styled it. Especially the bright, block colours. I don’t wear enough skirts like this.

  • Reply jaana October 7, 2013 at 1:48 pm

    i love the date night look because of all the pretty textures. but the green blouse is a color to contend with! so pretty

  • Reply FripperyVintage October 7, 2013 at 2:24 pm

    Love all of these, who knew you could wear an animal print pencil skirt in so many cute ways!

  • Reply Berty Morales October 7, 2013 at 5:30 pm

    Thank you for this amazing tips. I own several of them and I do not wear them as often because I have no clue some times of how :(. This post was very helpful, and I am in love with all of your looks!

  • Reply Jessica October 7, 2013 at 8:56 pm

    Wow! This skirt is so beautiful! I bought one like this a long time ago, but never realy wore it. I think tomorrow I’ll give it a try!

  • Reply Michelle October 7, 2013 at 10:11 pm

    Girl, I have that skirt and it’s my favorite. I like it so much, that I also own the dress in the same fabric. I know. Insanity.

    • Reply Jessie Artigue October 13, 2013 at 2:15 pm

      I don’t blame you AT ALL. I wear it all the time, and the fact that they keep making the same skirt in new prints means that it exists as several versions in my own wardrobe. :)

  • Reply Yolennie October 8, 2013 at 10:09 am

    I absolutely adore your hair in those photos :) Love your mixing and matching of different bold colors and prints. I seriously need to learn from you how to stack and layer accessories!


  • Reply becky October 8, 2013 at 3:36 pm

    Jessie~You look FANTASTIC! Love how you styled it. You make mixing prints look so easy!

  • Reply paige - house of ginger October 9, 2013 at 2:08 pm

    the last one is my FAVE!! and you look so freaking stunningly gorgeous in these photos.

  • Reply Five Favorites: Vol.11 October 28, 2014 at 12:40 pm

    […] Style and Pepper How to style a stretchy pencil skirt. I love the mixed patterns here. Just trying to work up the […]

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