Breathe New Life Into Your Black Pencil Skirt With These Outfits
We all have (at least) one black pencil skirt in our closets somewhere, and while the staple is certainly useful, when was the last time you were actually excited to wear it? Right… So, in an effort to help you get excited about the essential again, we're bringing you a little street style inspo to show you that what seems like a simple skirt can actually lend itself to a next-level look. See just what we mean in our black pencil skirt gallery.
Use this look as an opportunity to test drive this season's mid-calf boot trend.
Three elevated basics come together perfectly in this look.
Don't be afraid to play with proportions and layer a longer blouse (or even a dress) over your skirt.
This unexpected combination of belted jacket, pencil skirt, and sneakers is really working for us.
For a night out, throw on a camisole and mules.
If you're committed to your all-black wardrobe, spice things up with statement accessories.
Take cues from Alexa Chung and give your look a hint of prep by throwing a sweater over your shoulders.
Sometimes, just combining basics is the best idea.
Utility-inspired boots balance out a slit skirt and blouse perfectly.
The oversize blazer is pretty much always a good idea.
Who said all-black has to be boring?
If the temperature requires heavy-duty outwear, contrast your sleek skirt with an oversize parka and knee boots.
You can never go wrong with a button-down and booties.
Pair your skirt with a patchwork jacket for a model-off-duty–inspired look.
A cozy sweater and statement clutch go with literally anything.
Don't be afraid to mix sport-inspired pieces with classics.
Now, of course, shop our curated selection of black pencil skirts.
Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. Upon joining, she was a senior about to graduate from business school at USC. Fast-forward to 2025, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was just starting out. Currently, she focuses on a weekly mélange of shopping content and her Trust Me—Buy This newsletter. As far as her personal style goes, she's largely drawn to neutral, classic pieces but will always make an exception for something colorful or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a party is dressing up for one. On her downtime, she can usually be found at home eating something delicious and trying to force her husband to watch Summer House.
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