Fall & Winter

5 Modern, Sexy Ways to Wear a Pencil Skirt

There’s nothing more feminine than a shapely pencil skirt, and this season they are hotter than ever. The basic black or gray pencil skirt that many of us have worn is still alive and well, but there is a slew of other, more fashion-forward options that are much more fun to try out. Here are some of the latest pencil skirts, along with 5 modern and sexy ways to wear them.

Olive leather pencil skirt and floral blouse

1. Wear a Leather Pencil Skirt with Ankle Booties

Meghan Markle’s love of leather pencil skirts has made them extremely popular at the moment. Leather pencil skirts are sleek and a little edgy, and they look great paired with a silky shirt or blouse.

Even if you’re not particularly into leather, a touch of it can elevate your style game. This cool, black, faux leather paneled pencil skirt, for example, is a mix of fabric and leather. The strip of leather on the front of the skirt is just enough to give you a look.

The stretchy fabric makes the skirt lighter and comfier than an all-leather skirt. All you need to do is add a silky blouse to keep a black leather skirt from looking too harsh. The wrap-front, gathered hem blouse is an excellent choice because it ends high at the skirt’s waistband, but there’s some breathing room for your mature middle.

You could wear this black leather pencil skirt with sky-high pumps, but ankle booties are more interesting, edgy, and youthful. The slender heel on these black suede booties looks ultra-elegant with a sleek pencil skirt.

 

2.  Pair a Ladylike Blouse with a Tie Waist Pencil Skirt

There are many tie-waist style pencil skirts available this year, and that’s because they look classy but not stuffy —a look that every woman is aiming for these days. This beautiful double-weave tie-waist skirt in a gorgeous shade of red is a lovely choice for work when paired with a feminine blouse, heels, and a high-quality leather bag.

Ladylike blouses with ruffles, bows, and floaty sleeves are easy to find at the moment and pair really well with any pencil skirt, not just this style. I think cream or white looks best, so if you’re wondering what to wear with a red pencil skirt, I would go with something like this.

Snakeskin print pumps are sophisticated and add just the right amount of texture to this beautiful pencil skirt outfit.

 

sequin pencil skirt pink sweater

3.  Choose a Cashmere Sweater to Wear with a Sequin Pencil Skirt

 

You’ll look like you stepped off the red carpet this holiday season if you choose to wear a sequin pencil skirt.  The trend has exploded. This gorgeous silver sparkle pencil skirt lights up a room and is perfect for an upcoming holiday party. Wear it with a luxe hot pink cashmere sweater! Add a glittery gold evening bag from Kate Spade and some sexy patent leather evening shoes, and you have a first-class look.

 

Wrap Tops - Red Striped With Pencil Skirt

4.  Mix a Relaxed Plaid Shirt with a Tailored Black Pencil Skirt

Now here’s a classy look for someone who is wondering what to wear a pencil skirt with and wants a new idea. Take a black pencil skirt and pair it with a striped waist tie blouse.  Finish off your outfit with a classy black bag and black pumps.

 

5.  Combine Leopard with a Lace Pencil Skirt

Like sequin pencil skirts, lace pencil skirts have gained popularity for evening affairs. This black lace skirt is a beauty. Lace is so delicate and feminine that when combined with a bold animal print, you get an exciting, sweet, yet aggressive vibe. Of course, a pair of sexy black pumps with a jeweled strap and a tiny velvet evening bag adds to the luxurious look.

These are just a few of the latest ways to wear a pencil skirt.  There are no rules for what to wear with pencil skirts, so feel free to mix and match as you please and create your unique outfits featuring pencil skirts. If you have some great ideas for what to wear with a pencil skirt, please let me know!

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Meet the author

Deborah Boland

Deborah, a former Fashion & Lifestyle TV host and Image Consultant, understands the style challenges women face in their 40s, 50s, and 60s. As the founder of Fabulous After 40, she helps women tweak their chic and embrace fashion with confidence—so they always look and feel amazing.

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