3 Ways to Style a Classic Pencil Skirt

A classic pencil skirt is a go-to work essential, but today I wanted to expand on its style range, taking it beyond the office.

With any outfit, incorporating a mix of textures, prints, and fabrics is what makes your look interesting (Google Iris Apfel to see the absolute queen of interesting outfits), so each of today’s looks capitalize on that concept. I chose to style this pencil skirt in three ways: with a bit of edge, a day to night option, and a classic office ensemble.

With a bit of edge > a graphic tee + leather jacket + animal print heels

A leather jacket and graphic tee are unexpected pairings for a traditional pencil skirt, and that’s what makes them such fantastic compliments. Add in a bit of print-mixing with a pair of animal or floral shoes, and you’re making the outfit that much better.

If you work in a casual or creative environment, you could absolutely wear this look for the office. Since my workplace is conservative, I would save this look for a networking event or a meet up with girlfriends. It’s business–but with a little more fun.

As an easy day-to-night ensemble > striped blouse + strappy heels + animal print clutch

This striped button up blouse is a given for the workplace, but it can also become a perfect date night look by swapping out your pumps for a pair of strappy heels and a printed clutch. Layer on statement jewelry for a touch of drama, and you’ve transitioned from day to night in under 10 minutes.

wellesley and king-pittsburgh blogger-jcrew pencil skirt-7
wellesley and king-pittsburgh blogger-jcrew pencil skirt-7
wellesley and king-pittsburgh blogger-jcrew pencil skirt-7

No-fail classic and ladylike > a floral blouse + classic pumps + long wool coat

At the end of the day, styling with a feminine blouse and a classic wool coat is a no-brainer. This time of year, I gravitate to anything that resembles spring, so pink florals and a blush coat are exactly what I need to keep warm yet welcome the upcoming season.

wellesley and king-pittsburgh blogger-jcrew pencil skirt-58
wellesley and king-pittsburgh blogger-jcrew pencil skirt-58
wellesley and king-pittsburgh blogger-jcrew pencil skirt-58
wellesley and king-pittsburgh blogger-jcrew pencil skirt-58

A pencil skirt goes beyond your 9 to 5 with these versatile styling ideas. Which look is your favorite? How would you style it differently?

 Pin it for later!

wellesley and king-pittsburgh blogger-jcrew pencil skirt

What are your thoughts?

This site uses Akismet to reduce spam. Learn how your comment data is processed.


  1. Hello Lauren,
    thanks for the inspiration, these looks are great! my favorite is the ladylike floral blouse and day coat. Although, i’ve been leaning towards the graphic t and animal print. well done, keep it up!

    Posted 2.12.18 Reply
    • Thank you, Rachel! I’m glad you stopped by to read. I’m with you, I think the classic coat and floral blouse is my favorite of the three, too!

      Posted 2.12.18 Reply
  2. Pamela wrote:

    The pencil skirt is absolute must-have! I like the way it sits. In my opinion, this is the best bottom piece for ladies who want to show off their femininity and professionalism during work hours. Plus, this garment makes a real impression on every man. I made an article about pencil skirts for work, and want to share with you my favorite outfit ideas: http://wardrobefocus.com/pencil-skirts-for-2018-best-styles-for-work/ Hope you gonna like it too.

    Posted 6.15.18 Reply

Follow @wellesleyandking on Instagram

  • One week until Christmas. How on earth did this happen?! 🤷🏻‍♀️ I feel like I haven’t even had a chance to watch a single Christmas movie or bake any cookies. Anyone else feeling like the holidays came out of nowhere this year?! #holidaygiftideas #maternityfashion #christmasoutfit #holidaystyle
  • Soon enough ill be able to enjoy a cocktail again. Until then, i just photographed these for you guys.💕 #wellesleyandking #theblogsocieties #cocktailrecipe # #pittsburghfashionblogger #livebeautifully #tnchustler #chooselovely
  • Getting ready to take this little number for a spin this weekend. Here’s hoping I can fit my swollen feet into some halfway cute shoes! #holidaystyle #inspirepregnancy #maternityfashion #lbd (link in bio to shop fellow mamas-to-be!💕)
  • Getting ready feels like such a chore nowadays with this belly in the way. BUT when I do feel like making myself look halfway presentable, I always use my @t3micro curling irons and wands. Nothing curls my hair faster or keeps the curl longer. Definitely worth the investment—great holiday gift idea for those on your list, too! #unsponsored #beautygifts #holidaygiftideas
  • The details of our baby shower/gender reveal from last weekend are on www.wellesleyandking.com today! #genderrevealparty #babyshower #babywellesley #wellesleyandking
  • How many of you guys send out Christmas cards? Do you get professional photos for them? It’s one of my favorite Holiday traditions and definitely the most fun season for mail! #holidayphotoshoot #christmascards2018 #jcrew #inspirepregnancy

Follow Me!

Ready to build a wardrobe to last?