It’s complicated: my relationship history with the Pencil Skirt

From the grainy reels of early movies to the highly produced media we know and love today, there are few enduring fashions. A survey of the last few decades reveals trends cycling in and out of vogue (in both the metaphorical and the very literal sense of the word.) A discerning eye might be able to link the passage of time, the evolution of certain pieces.

However, one garment seems to have defied evolution. Black and white photos from the 1950s show people in tapered pencil skirts with matching jackets. In the 80s, the power suit added shoulder pads but kept the pencil skirt. On the set of the American adaptation of The Office, a number of characters frequently appear in pencil skirts. Made in a variety of lengths, fabrics, and fits, to this day, they demand space in the closets or fashion consciousness of many.

The pencil skirt holds a place of honor in fashion archives. It’s an iconic staple which has survived decades of shifting trends. I will admit that most people in my social circle are not avid wearers of pencil skirts for a variety of reasons, but I have been coming around to them lately.

Pencil skirts, which can be traced in their modern iteration to the 1940s-50s, grew out of a trend of shortening and tapering skirts. These early skirts earned their share of derision, as they altered the gait of wearers, forcing them to take smaller, faster steps. In the 50s and 60s, the pencil skirt became ubiquitous, representing empowering professional wear to some while becoming the subject of hypersexualization to others. Though the lengths have fluctuated slightly and other fabrics have been introduced, the pencil skirt itself has endured and engrained itself as a wardrobe staple.

This black and white illustration shows vintage pencil skirt silhouettes.
Photo by the author. The author stands behind her garden, admiring the languid tendrils of cucumber vines and the bright orange marigolds which match her orange pencil skirt. She pairs the skirt with a grey top, black cardigan, and friendly dog.

If you spend a little time digging into scholarship on fashion, you might see some fascinating pieces on the meaning of the pencil skirt, its significance as a symbol of professional  empowerment, its seemingly antithetical significance as a symbol of the imposition of oppressive norms, and somehow, at the same time, its role in expression of sexuality. These are all fascinating angles, which come through various scholarly lenses. If you’re looking for your next fashion related rabbithole, this is a great one to explore.

Rather than digging into or debating these theories, I thought I would spend this piece meditating on the significance of the skirt in my own life. I talk a lot about the cyclical nature of the fashion industry. We’ve seen the waistbands of jeans go down, up, and down again. We’ve seen jeans flare wide, taper to a skinny, and then start to flare again. What I haven’t really considered is my own cyclical use patterns related to fashion. My own preferences have changed over time, as my new and current penchant for pencil skirts proves.

My own personal history with the pencil skirt started in my childhood. I have one aunt who particularly loves to collect vintage and eclectic pieces of clothing. Once I hit my teens, she would lovingly present me with one or two pieces from her wardrobe as a gift for Christmas or my birthday. The generosity of this sentiment is something I don’t wish to impugn. However, at this stage of our lives, we were wildly different physical sizes. Every time she presented me with one of her hard-sourced treasures, I would feel a tug of dread. I would exclaim over how lovely it was and then, with the encouragement of my family, I would try it on. Without fail, these never fit my body, which could easily be predicted based on a quick glance at the two people engaged in this unidirectional clothes swap. Sometimes, I wouldn’t even be able to shimmy the pencil skirt up past my hips, let alone zip it.


As a teenager, it’s not like I was attending frequent business meetings which would merit such attire, even if one of them were to fit me. Even as an adult, the negative emotional connotation I had cultivated left me with a sour taste in my mouth when I thought about choosing to wear a pencil skirt. And to be clear, it’s not an immensely practical outfit. The cut is a little severe. There’s frequently little stretch, which offers limited leeway. Anything short of a perfect fit, and the skirt is nothing but a disaster which will ride up or down the entire day. If the skirt is too long, the wearer will be forced to shuffle awkwardly like a penguin trying to protect an egg on its feet. A slit can ameliorate some of the mobility issues, but it comes with its own risks, particularly in regard to bending over.


Since then, I’ve devoted some serious energy to reconsidering the way I think about clothing and myself. I’ve found and cultivated a general sense of okayness. I try to find clothing that fits me, rather than allocating my mental energy to the anguish which trying to fit into clothes can cause.

Somewhere along this journey, I’ve discovered I really am a pencil skirt person. I actually, unironically, love wearing this garment. I can trace my newfound affection for this particular garment to a specific moment. Ninety days after the passing of my paternal grandmother, my family gathered for a traditional Greek Orthodox remembrance service. This was a sad and overwhelming time for all of us, combined with the stress of hosting 14 family members from out of town, cooking the traditional foods, and generally keeping everything together. I took a couple days off work to help out with the cooking, cleaning, and soaking of wheat berries to make koliva.

Truthfully, I had almost no energy for myself at this stage. After having not worn black dress pants in nearly two years, putting them on felt terrible. Casting those aside, I rifled through my closet, looking for anything somber and dressy. Without even trying it on, I just grabbed a dark woolen pencil skirt from the back of my closet and threw it in the tote bag with the rest of my clothes for my trip home.

Photo by the author. The author stands next to some rather overgrown basil plants in her garden. She is dressed in her favorite pencil skirt, a mint green, faux suede garment that falls just below the knee. She pairs that skirt with a gray shirt.
Photo by the author. The author stands next to the corner of a brick wall, with the light of a setting sun draping gently over her shoulders. The author wears a vintage purple and black pencil skirt, the same one she wore to her grandmother's memorial service. She pairs this skirt with a grey top and black cardigan. Seemingly oblivious, the author's dog enjoys the cool embrace of slightly overgrown grass near the author's feet.

In the craziness of the weekend, the joy of gathering and the sharing of grief, I did not really think about it again until I dressed for the service. Something about stepping into the skirt just made me feel put together, polished. I felt in control for the first time in a long time. I can’t fully tease out why, but something about pairing a simple black blouse with the skirt gave me a sense of poise which I so needed in that moment.

Since then, my opinion on pencil skirts has softened. I would never wear one every single day, and I can acknowledge the many practical failures of the design, but I still really like them. I like garments that hit at my natural waist. I like that I can tuck a simple top into a skirt and suddenly look and feel polished. I feel powerful and sleek, like a duck gliding through still water. My legs are moving fast out of sight, but to the casual observer I am a paragon of grace and efficiency. Clothing can play a powerful role in self expression and perception. The right piece can lift moods, inspire creativity, or empower a lifestyle change. For me, the pencil skirt found me at the right time.

Given the long history of pencil skirts, there is an enormous assortment of colors, styles, fabrics, and details within this category. I have slowly accumulated a small collection of this once odious garment. I have a stunning soft mint green pencil skirt made of vegan faux suede skirt, which I probably wear most. I have an orange linen iteration, which I generally try to wear for events which primarily involve standing because I discovered after I bought it that it wrinkles at the merest thought of sitting. A black beaded one serves that dressy pencil skirt energy. And, as a piece de resistance, my aunt, that same one from the beginning of the story, sent me an unforgettable lilac quilted pencil skirt, and this one actually fits me. I have never worn it in public, but I am just waiting for the day I get invited to a winter wedding or some other event which would justify owning this piece of clothing.

The pencil skirt represents the power that clothing can hold in how we see ourselves, while also serving as a testament to the constantly changing nature of personal preferences. Independent of trends in the wider world of fashion, my life circumstances and general attitude toward the way I dress have changed. To be fair to my past self, I now own this garment in sizes which are appropriate to my physical size. I also do work in an office setting, which is definitely a more appropriate setting for the wearing of pencil skirts than a high school.

Take a moment to consider your past self; dig back a decade or perhaps even longer. Is there something you currently wear that past-you would have loved? Is there something you wear that past-you could not have believed you would ever pick? This can be a fun exercise to understand the way fashion’s role in your life can change as you and your lifestyle continue to grow and evolve.

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