How to Style a Pencil Skirt
Content editor
Else Hutt
What to wear with pencil skirts for different occasions
There’s a reason pencil skirts have long been synonymous with workwear: they're the perfect foundation to endlessly smart looks. Our current go-to is this jersey pencil skirt that's designed with a shaped, elasticated waist. Just tuck in a formal shirt and add a neat cardigan or jacket, then finish with pumps before heading to the office.
For more casual days, we’re coveting Finery’s midi style in black or green. It’s cut to a flattering regular fit with oversized buttons that nod to the utility trend. Pair it with a short-sleeved T-shirt and chunky boots and you're good to go.
Special occasions call for extra sparkle: cue our sequinned midi skirt. For a guaranteed show-stopper, style it with the coordinating top and stilettos, or create easy contrast with a slinky black cami and kitten heels.

The best tops to wear with pencil skirts
If you’re wondering what top to wear with a pencil skirt, you can’t go wrong with a shirt or blouse. Our button-through shirt is cut to a comfortable relaxed fit so it can be tucked in easily for a considered finish.
For off-duty days when comfort is key, a jersey pencil skirt fits the bill. This striped style from Joules has an elasticated waist and side slits for ease of movement. Throw on a cosy sweatshirt to keep snug.
Alternatively, you can always rely on the ultimate wardrobe staple: a classic cotton T-shirt. We love our slim-fit tees: made from super-soft ribbed jersey they come in a whole host of colours.
When colder weather hits, it's time for throw-on-and-go knitwear. Our merino wool jumpers are made in a fine knit that make them perfect for layering and finished with ribbed trims for a smart touch.

The best shoes to wear with pencil skirts
The streamlined silhouette of a pencil skirt lends itself perfectly to understated shoes. So, for everyday dressing opt for classic ballet pumps or loafers. We’re currently coveting these simple red slip-ons detailed with a neat bow and rounded toe. Alternatively, our black leather penny loafers are ideal for workwear.
When it comes to fancier occasions, look to a timeless court shoe in an easy-to-style colour. Our cream heels are made with Insolia technology that cleverly redistributes weight away from the balls of your feet, so you’ll be comfy all day long.
If you’re looking for more of an in-between shoe, try a kitten heel. The smaller heel will give your outfit just the right amount of lift, but is still easy to walk in. Our leather sling-backs tick all the style boxes but are still a comfortable choice thanks to the elasticated strap.
Published 7.22.2025
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