A Modern Approach to Vintage Pencil Skirts

Who else watched Mad Men and envyed Joan’s presence (and bum) when she strutted into the office in a perfectly fitting pencil skirt? In high school, I loved the idea of wearing pencil skirts when I eventually entered the work force. I remember purchasing a couple when I graduated college because they exuded power and professionalism. However, when I stepped foot in my first corporate office at a retail company, pencil skirts were nowhere to be seen. So mine secured a spot in the back of the closet.

Fast forward almost 10 years and “professional work-wear” is starting to get its moment in fashion again. Now I enjoy uncovering vintage pencil skirts that served women who were working hard to break their way into male dominant professions.

Since I still work in a creative office I prefer to balance the professionalism of the skirt with something really casual. Enter: the sweatshirt. The juxtaposition creates a more modern look. As someone who’s 5’3″ my favorite place to find vintage sweatshirts that fit are in the boy’s section. That’s wear I found this blue one and I can’t get enough of it!

As a shorty, it’s important I add height as the skirt hits at my mid calf. I also wanted to maintain a bit of whimsy so I wore my pinky-nude lips heels.

Etsy is a great source for vintage apparel but the sheer amount of product can be overwhelming. So I’ve scoured the site to find my favorite pencil skirts and sweatshirts if you wanted to re-create the look.


Shop my favorite vintage sweatshirts and pencil skirts on Etsy here!


Thrifted Vintage Sweater // Thrifted Vintage Skirt // Thrifted Vintage Levi’s Denim Jacket // Sam Edelman Heels // Warby Parker Glasses // Tarte Lip Paint in “Twerk”


Photography by Jacob Baccus

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