5 Pencil Skirt Outfits to Take You Through the Week and Beyond

Pencil skirts often have a reputation for looking stuffy and old school, which is silly—they're anything but if you know how to style them. Instead of looking at your black skirt as that boring ol' piece for the cubicle life, think of it as a blank canvas for a statement top or accessory that shows off your personality. Speaking of personality, pencil skirt styles can range from denim designs with a side slit to flowy at the bottom with a pretty floral print. If you need more inspiration as to how to make your everyday pencil skirt feel fresh and current (and for more than the office), scroll down for some quick style tips, then shop the exact pieces you're still missing.

1. The Office-to-Happy Hour Outfit 

If you work in a more corporate office, invest in a black pencil skirt. The bottom might be a bit tame, but consider it a blank canvas for a bright floral top or a colorful handbag. You may even get away with wearing a pair of open-toed sandals that are trendier than what the HR handbook states. With the right accessories, you can easily take this bottom from work to happy hour any day of the week.

Shop the pieces: 1. Rebecca Taylor chiffon top (opens in new tab), $275; 2. Banana Republic skirt (opens in new tab), $98; 3. Shashi earrings (opens in new tab), $36; 4. Frame Les Second bag (opens in new tab), $450; 5. Zara heeled mules (opens in new tab), $50

2. The Office-Casual Outfit 

For those with more freedom at their 9-to-5, give this tiger print pencil skirt a try. It definitely makes a statement, which is why you should tone it down with a plain white blouse, gold hoop earrings, and black slides. You may even want to repeat this outfit on the weekend (swap the tee for a sleeveless crop top).

Shop the pieces: 1. Mango blouse (opens in new tab), $50; 2. Carolina Herrera skirt (opens in new tab), $1,490; 3. Shashi earrings (opens in new tab), $55; 4. Clare V. bag (opens in new tab), $118; 5. Kaanas sandals (opens in new tab), $65

3. The Breakfast-With-Clients Outfit 

For meetings where you want to look professional but not stuffy, this bold floral printed skirt is a good way to break up a plain-shirt-and-blazer combo. The skirt is a good conversation starter—you'll definitely earn some compliments from the room. Add on a structured accessory like this crossbody bag and slingback heels for a polished ensemble.

Shop the pieces: 1. Mango top (opens in new tab), $30; 2. Eliza J blazer (opens in new tab), $78; 3. Diane von Furstenberg skirt (opens in new tab), $248; 4. Strathberry tote (opens in new tab), $955; 5. Prada slingback pumps (opens in new tab), $690

4. The Weekend Outfit 

Come Saturday, swap your heels for sneakers and a traditional pencil skirt for a more laidback denim version. (The side slit in the middle is definitely NSFW.) Instead of a blazer, slip on this tie-dye turtleneck, which is a warm enough layer to take you from end of the summer into fall temperatures.

Shop the pieces: 1. Proenza Schouler turtleneck top (opens in new tab), $590; 2. 3x1 denim skirt (opens in new tab), $245; 3. AllSaints leather tote (opens in new tab), $378; 4. Veja sneakers (opens in new tab), $135

5. The OOO Outfit 

The pencil skirt you should pack when you take that much needed PTO. It has the same structure as your 9-to-5 look, but with sexier details, like side ruching and a high-rise slit. The vibrant florals also transport your senses from the cubicle to faraway beaches. Trade in your work tote for a smaller, cuter bag and top off with a floral bucket hat. Happy travels!

Shop the pieces: 1. Reformation linen top (opens in new tab), $148; 2. Madewell bucket hat (opens in new tab), $25; 3. Altuzarra midi skirt (opens in new tab), $397; 4. By Far bag (opens in new tab), $372; 5. Cocobelle slides (opens in new tab), $129

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