How To Wear A Pencil Skirt

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Wardrobe Staple: Pencil Skirt

The pencil skirt is one of the most timeless silhouettes in fashion — and with a good reason. Pencil skirt outfits are a flattering look — when worn right — on just about every figure. With a tucked-in shirt or belted jacket, the pencil skirt gives you a long, lean line. In addition, it shows the legs, which keeps it decidedly feminine.

A black pencil skirt is a wardrobe staple, and can be worn with everything from a matching jacket for a suit look to a slinky camisole for a night out.

Wear a Pencil Skirt With a Peplum Top

One of the freshest ways to wear the pencil skirt is with a peplum top or jacket. The belted silhouette makes your waist look tiny and plays up an hourglass shape, while the long pencil skirt gives you a slim, tall look. This look is perfect for creating a waist on a boyish figure or slimming a full waist. Either way, it’s a chic and glamorous look that never goes out of style.

Wear a Pencil Skirt With a Feminine Blouse

One of the most ladylike ways to wear the pencil skirt is to pair it with a feminine blouse. Opt for something lacy or ruffled, or a sheer top. Florals and other pretty prints also work with the pencil skirt. And nothing is more timeless (and Jackie Kennedy-esque) than a bow top paired with a pencil skirt. Add traditional accessories — like pearls — for a can’t-fail feminine look.

Colorblock With a Pencil Skirt

Try a skirt in one color with a top in another complementary hue for a simple — but cool — approach to colorblocking. Want to amp it up even more? Add shoes and bag in two more colors. The simple lines and classic shape of the pencil skirt let you experiment with it more than a funkier skirt with more design details, so it’s perfect for mixing it up, colorwise.

Wear a T-Shirt With a Pencil Skirt

t-shirt-with-pencil-skirt — Getty Images / Christian Vierig

While many women associate pencil skirts with office wear, you can easily dress down this wardrobe workhorse for the weekend. Perfect for brunch with the girls or date night, wearing a pencil skirt and t-shirt is effortlessly chic. Dress up a plain tee and pencil skirt with a statement necklace, or opt for a graphic print t-shirt for a funkier look. While this combo won’t work in a formal office environment (sorry, women of Wall Street), this pairing is perfectly at home in a more casual or creative work place.

Wear a Pencil Skirt and Crop Top

croptop-with-pencil-skirt — Getty Images / Dimitrios Kambouris

Spoiler alert: Crop tops are back! This time around the crops are more sophisticated than their 90s predecessors though, don’t worry. Instead of a simple cotton tee or tank, crop tops are available in a variety of luxe fabrics and in eye-catching prints. Create a look that is equal parts sexy and chic by pairing a crop top with a longer pencil skirt.

Try a Leather Pencil Skirt

Been wanting to try a leather skirt? Skip the flippy leather or skater skirts and opt for something flattering and chic like a leather pencil skirt. You’ll be amazed at how basic — and wearable — it is, going with everything from lacy tops to wool jackets.

Printed Pencil Skirt

J.Crew is a great source for pencil skirts (and tons of other work-appropriate styles, obviously), in both classic fabrics like wool and stretch, as well as denim and lace. This option is great for fall, and can easily transition to winter with tights the right accessories.

Colorful Pencil Skirt

If you’re looking to make a statement in the office (or just need a fun, colorful update), try a pencil skirt in a bright, rich color like robin’s egg blue. This skirt from Elizabeth and James has stretch — which makes it ultra-flattering and perfect for layering.