How to Rock a Pencil Skirt 101

This classic piece works with all body types and heights, plus it's versatile enough to wear 365 days a year.

By Beth Levine November 9, 2017

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Miranda Kerr in a pencil skirt and tee from H&M

Image: Courtesy H&M

One age-old dilemma for us office workers is what to wear to work in Houston’s pretty-much-year-round warm weather. The answer? The pencil skirt.

This time-honored classic works with all body types and heights and is versatile enough to wear 365 days a year in H-Town—though at that rate, you might want to get more than one. To help narrow the playing field, here are our top picks for pencil skirts on the market today, along with suggestions for the best ways to wear them. 

H&M Pencil Skirt: $12.99

Seriously, H&M has about half a dozen pencil skirts all for under $25, so you can get more than one.

Pairing Option: A tailored button down. Why not pair one classic with another?

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Slip-on pencil skirt from Express

Express Pencil & Work Skirts: most under $70

I bought three full suits when I first started out in corporate America: pants, skirt, blazer—all from Express. Two in black, one in grey. I still have them a decade later.

Pairing Option: A tank top paired with a jacket. Yes, we know: Sometimes you can’t do the whole bare shoulder thing at the office, but it’s hot here people and chances are your office feels like Antarctica anyway. Pro tip: Most of Express' suiting has matching jackets. After work, just lose the jacket.

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Pencil skirt and suit from Ann Taylor

Ann Taylor Season-less Stretch Seamed Pencil Skirt: $89

Yes, Ann Taylor can be pricey, but as of late most of their work wear is...wait for it…machine washable! Yes, finally! That alone makes it so worth the price and the Season-less comes in quite a few varieties to choose from.

Pairing Option: Believe it or not, even paired with a stylish tee and heels, this classic is still office-worthy. 

J. Crew Suiting Skirts: $79 to $138

Hey, remember how popular this store used to be? While they might not be the first name that comes to mind for the newest trends, J. Crew still rocks the classics with their pencil skirts coming in three fabric selections: Italian Stretch Wool, Two-way Stretch Cotton and Super 120’s Wool.

Pairing Option: A sweater for those few days of the year it's actually nippy here in Houston. Bonus round: If it’s cold enough to wear a sweater, you might just get to rock your pencil skirt with boots! 

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Pencil skirt from Theory

Splurge Item

I have been a Theory addict for over a decade thanks to my sister, whose wardrobe budget is a lot higher than mine. That said, while they may be uber pricey (at around $215 retail), Theory skirts (and pants) are literally some of the best on the market and give you just the right amount of what we call “work booty.”

Pairing Option: For Theory, anything.

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