7 Timeless Pencil-Skirt Outfits for Any Age

last updated 7 April 2020

Pencil skirts are without a doubt a closet staple that every woman should own. This silhouette is one that surpasses time and trend, and we are here to prove it to you with the timeless pencil-skirt outfits ahead. Thanks to their simplistic lines and typically conservative length, pencil skirts are not confined to a certain age group nor personal style, either.

Celebrities like Kendall Jenner and Reese Witherspoon demonstrate how to style this timeless skirt in a way that fits your own personal style. Whether the addition of a simple button-down for work is what you're looking for, or the combination of a newsboy cap and velvet ankle boots is more your vibe, fear not, because the pencil-skirt outfits ahead will satisfy a spectrum of tastes and ages.

Keep reading to see the pencil-skirt outfits you should be trying and to shop some of our favorites.

Jennifer Lopez

7-timeless-pencil-skirt-outfits-for-every-age-1957026-1477685006

What You'll Need: A thin white knit, nude heels, and simple jewelry.

Kendall Jenner

7-timeless-pencil-skirt-outfits-for-every-age-1957025-1477685006

What You'll Need: A newsboy cap, a choker, a white tee, and velvet boots.

Lauren Hutton

7-timeless-pencil-skirt-outfits-for-every-age-1957024-1477685006

What You'll Need: A cable-knit sweater, a gray tee, and sneakers.

Jessica Alba

7-timeless-pencil-skirt-outfits-for-every-age-1957028-1477685006

What You'll Need: Hoop earrings, a black tank, and black pumps.

Sarah Rutson

7-timeless-pencil-skirt-outfits-for-every-age-1957022-1477685005

What You'll Need: A structured poplin top, sneakers, and timeless shades.

Reese Witherspoon

7-timeless-pencil-skirt-outfits-for-every-age-1957023-1477685006

What You'll Need: A classic button-down, printed loafers, and a polished bag.

Amal Clooney

7-timeless-pencil-skirt-outfits-for-every-age-1957027-1477685006

What You'll Need: A fitted tee, pumps, and a statement bag.

Shop pencil skirts we love:

The Row

Rabina Stretch-Jersey Midi Skirt

ASOS Curve

Two-Piece Midi Skirt

Rejina Pyo

Scout Faux Leather Midi Skirt

Theory

Silk-Satin Midi Skirt

By Malene Birger

Maliva Twill Midi Skirt

Monse

Asymmetric Gingham Wool and Cotton-Blend Midi Skirt

Topshop

Ring Buckle Midi Skirt

AlexaChung

Faux Patent-Leather Pencil Skirt

Sara Battaglia

Cady Pencil Skirt

Sies Marjan

Cynthia Ombré Faux Fur Midi Skirt

James Perse

Stretch Cotton-Blend Jersey Midi Skirt

Ganni

Jerome Lace Midi Skirt

16Arlington

Patent-Leather Pencil Skirt

This post was originally published at an earlier date and has since been updated.

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Lauren Eggertsen is currently the editorial director of Who What Wear and has worked at the company for over nine years, where she started as an associate editor and has since worked her way up. Lauren has worked in the Los Angeles and New York Who What Wear offices but currently calls L.A. home. Here, she leads and manages Who What Wear's editorial team and oversees all editorial content. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many celebrity cover shoots, including big names like Kaia Gerber, Normani, and Sabrina Carpenter. She has also attended multiple fashion weeks, including New York, London, Milan, and Paris, where her style has been featured on sites such as Vogue, Harpers Bazaar, and Elle.