Closet Essentials: The Pencil Skirt

This slim-fitting classic is the backbone of the modern working woman’s wardrobe. Maximize its versatility with our shopping and styling tips.

Christian Siriano Ready-to-Wear, Fall 2010

Photo from

Straight skirt shapes have come and gone throughout fashion history – hobble skirt, anyone? – but it wasn’t until Christian Dior created his ultra-femme “New Look” in the 1950s that the modern pencil skirt was born. Dior’s curve-hugging, high-waisted, below-the-knee skirts were an instant success among retailers looking to minimize fabric costs and women looking for a practical alternative to the full-skirted silhouettes also popularized by Dior.

The two dominant silhouettes of the 1950s: the pencil skirt (left) and the full skirt (right), as seen on this vintage sewing pattern.

Since the pencil skirt’s debut on Dior’s catwalks, it’s enjoyed a number of comebacks as the go-to-silhouette for women of all ages, particularly in the 1980s and 2000s as part of skirt suit ensembles. With its curve-hugging shape, which flatters almost every body type, and longer length, which makes it work-appropriate, the pencil skirt is a versatile basic that can go from super sexy (think Bettie Page) to professional (think Joan on Mad Men) with the simplest of styling tricks. Our faves:

1. Silky tank

A simple tank, cami or shell in a luxe fabric like silk amps up the classic vibe of a simple pencil skirt and takes it from day to evening in no time flat. Extra points if you tuck it into a pencil skirt with an uber-high waist.

2. Retro sweater

The perfect way to look professional at the office while adding a bit of fun. A 50’s style cardigan – think fitted, round-necked, three-quarter sleeved, and hitting just at your skirt’s waistband – is the perfect way to give your pencil skirt a “sexy secretary” look.

3. Solid heels

Skinny-heeled stilettos can look too obvious with a pencil skirt. Try a platform pump with a chunkier heel to edge up your outfit. For fall, heels in the same colour as your skirt plus tights in that colour will make your legs look miles long.

4. Leather jacket

A cropped leather motorcycle-style jacket  in a buttery leather is an unexpected match for a pencil skirt, but it works. The key is to keep the shape fitted and cropped to balance the skirt’s slim silhouette.

Shopping for skirts…

There are two main types of pencil skirts out there; choose yours wisely.

The first kind is fitted – sometimes these are called body-con or bandage skirts – and hugs your hips and bottom. It’s tighter at the knees than it is at the hips. Choose this kind if you love to show off your curves, or if you don’t have any.

Stop Staring Fitted Pencil Skirt, $59.95, Daddy Os

The second kind of pencil skirt is straight – it is the same width at the bottom as it is at the hips. Choose this kind if you want to minimize your curves or look taller.

Agenda Stretch Pencil Skirt, 69.50, Banana Republic

Whichever shape you choose, there are universal markers of fit and quality you should look for when shopping for a pencil skirt. Weight and lining are important – invest as much as you can in a skirt that has both. Make sure the waist fits you comfortably without any gaps, and watch out for pulling around your hips. If the fit is off at the hip, the skirt will ride up when you walk – far from classy. And try to keep the length either at your knee, a couple inches above, or a couple below – too short or too long and you’re in mini or maxi territory.

Don’t forget the details! Cool details like buttons, slits, or a pattern can elevate your pencil skirt from workday basic to a statement piece you’ll reach for every time you want to look cool and classy.

Lamwood Stretch-Wool Pencil Skirt by The Row, $500, Net-A-Porter

Higgeldy-Piggeldy Pencil Skirt, $178, Anthropologie

Ecote Knit Pencil Skirt, $48, Urban Outfitters

Happy skirt shopping!

Share Button