Day to Night | Pencil Skirt

Okay, Monday came waaaaay to quickly, don’t you think? I don’t know if it’s because our weekend was so jam-packed, or because we have a busy week ahead, but I’m not quite ready for you, Monday!

Between the election, One Room Challenge Reveal, and packing for a trip, this week makes me a little nervous. Oh, and it’s my birthday this weekend…so lots going on! Let’s worry about all that later, and chat about the classic workwear staple…the black pencil skirt!

In my corporate days, pencil skirts were an integral part of my wardrobe…but of course, I paired them with colorful separates to keep them from being too stuffy. And actually, if you find a well-fitting skirt (like this one, now on sale!), they hug your figure in a subtly-sexy way, making them easily transition for a night out.

Let’s start with a more traditional workwear combination…a blouse and cardigan. And bonus, because virtually every piece in this outfit is now on sale!

The colors soften the overall look, while the whimsical print and touch of bling make the outfit stylish and interesting, but still keeping it business appropriate.

Finding the right fit for a pencil skirt can be tricky, especially for those of us with ‘a backend.’ The key is a little stretch so you can fit your natural waist, and have the skirt give enough to accommodate your hips. You definitely want a sleek silhouette that hugs your figure, so don’t be shy about it being too form-fitting.

Pencil skirts aren’t meant to be minis either, so look for one that hits just above, or just below the knee. The proper length, paired with a higher waist, creates a really long and lean leg-line, too! Just because you’re at work doesn’t mean you don’t want to look good! #amIright?

Fit Tip: This skirt fits like a (comfy) glove, but runs a little big, so I sized down to a 0P. Find it here in petite, and here in regular sizing. And look how darling it is on my mom here.

Sugarplum Style Tip: Work blouses can feel a little mundane, so I look for whimsical prints and added details like pleating or pretty buttons. It’s those little details that add more style to your outfit. I love the floral and ruffle of this blouse, too.

Fit Tip: The blouse runs large, so I recommend sizing down…I’m wearing a 0P. The cardigan is true-to-size, and I’m wearing an XS.

Now, who wants to keep two separate wardrobes…one for work, and another for weekend?! Not me! I like my clothes to play double-duty, so by adding a lacy top and sassy shoes, this skirt is ready for a night on the town!

The lace shows a bit more skin, but the longer skirt keeps the look classy. You could even add a blazer (like this one) for a work event, or a moto jacket (like this one) for girl’s night.

This skirt really goes a long way, and somehow manages to make every combination stylish. There’s a reason why pencil skirts are considered a wardrobe staple…they’re pretty much universally flattering, and suitable for so many occasions. Do you have a favorite black pencil skirt?

{Shop the Work Wear Look}

{Shop the Weekend Look}

Photos by the darling & talented Mary Summers.

*This post is created in collaboration with Nordstrom, but all clothes, styles, and sidewalk-strutting are my own. Thank you for supporting the brands that support Hi Sugarplum!*

Leave a Comment


  1. That skirt gives me all the happy feels. And your hair…it slays me. xo

    Posted 11.7.16 Reply
  2. Christina wrote:

    Extremely cute! I love the print and detail on the back of that blouse! I like clothes to play double duty, too, and as a stay at home mom I don't need work clothes but realized I don't really have anything to take it up a notch if needed. (I looove getting dressed cute each day so some of my day clothes are a little dressier) Do you have a favorite LBD that goes day to night?

    Posted 11.7.16 Reply
  3. You WEAR that skirt. #fistbump

    Posted 11.7.16 Reply
  4. The skeveless print blouse that you are wearing doesn't appear to be the same as the Nordstrom link?

    Posted 11.7.16 Reply
    • It looks like it sold out! 🙁 I'll watch to see if it comes back and let you know! xo

      Posted 11.8.16 Reply
  5. You always look classy and hip and cool at the same time!

    Posted 11.8.16 Reply
  6. Love love love your sense of style and creativity…keep up the positive vibrations!

    Posted 11.8.16 Reply
  7. Do NOT take in the negative energy of anonymous trolls that are still acting out on jr.high insecurities…we love you!

    Posted 11.8.16 Reply