How to Style a Pink Pencil Skirt For Work and For Play

Here’s a fun fact most of you will not know about me: in junior high I starred in a very low-budget production of Grease as the one and only head of the Pink Ladies, Rizzo. AKA the badass. AKA the slut. AKA the feminist queen with the short hair and I-don’t-give-a-f**k attitude.I know. You’re SHOCKED. 😏

Aside from the horror of singing on top of a track and dancing semi-suggestively around a fake bedroom in my PJs in front of an audience of peers and parents, I was super into the attitude - and the outfits.

(All photos by Andy Nichols)

Enter the Skirt

As you can imagine, when I found this 1950's wool pink pencil skirt while vintage shopping my mind immediately hearkened back to those conflicting days and I couldn’t wait to style it for every occasion.


Or at least two occasions. But I think you and I both know that there exists a myriad of options with a gorgeous, tailored pencil skirt.

Unless you don’t? If you want to see more styling options for this pink lady - just let me know in the comments and I’ll see what I can do for fall! 😘

She looks too pure to be pink - Rizzo

The looks

Outfit one is the sedate lady, the work lady, the “I’ll play by your rules but I’ll do it my way, in other words while wearing a pink pencil skirt” lady.


Black tights, oxfords, a turtleneck and simple accessories let the skirt do all the talking. And a beautifully made, heavy wool, vintage beauty like this skirt deserves to steal the spotlight. She shouldn’t have to compete with any office Becky for hers!


Outfit two is a fun girls day or date day outfit. Too casual for night, but just right for brunch and shopping or heading to a museum; funky enough to carry you through most occasions and still plenty casual not to get called out if you end up drunk and in...say...a ball pit. WHAT?! I swear that’s never happened...