Fashion Finds: Top 10 Pencil Skirts 

If you’re a woman over 50 who doesn’t own a pencil skirt, then, sister, time to get you up to speed! Pencil skirts are the most tasteful kind of sexy, and we have a few reasons why along with suggestions on how to style them.

  • Pencil skirts are timeless, easily paired with modern to vintage pieces.
  • Literally anything in your closet goes with a pencil skirt.
  • Pencil skirts hide body-shapers very well. Pick your favorite shaper, layer, and you’ll look like Beyonce’s long-lost sister in no time flat.
  • Pencil skirts come in a variety of lengths, from just above the knee to ankle-length.
  • Consider length when choosing your shoes. Booties pair nicely with either length, but a tall boot with a longer skirt will just look messy.
  • Absolutely wear sneakers with pencil skirts. Best paired with a casual tee or sweater on top.
  • Pencil skirts elongate the body, visually. For the short girls there are tons of options for high-waisted cuts.
  • It is important to consider proportion when building a pencil-skirt-oriented outfit. For longer skirts you can go with cropped jackets, or longer-line blazers and cardigans….basically the short/long extremes. With shorter, knee-length and above-the-knee-length skirts, keep the tops and jackets in the same overall length of the skirt, and choose slimmer silhouettes to keep from overpowering the skirt.
  • Belt it; skinny or wide belts make a great accessory.
  • A turtleneck and skirt in the same solid colors will absolutely make you look like a movie star. Layer on the bling with this outfit, of course.
  • Pencil Skirts are great real estate for patterned fabrics, as wearing them on the bottom half will be less overpowering to the rest of the outfit and are naturally slimming.

Here’s our 10 selections for the best pencil skirts to look fabulous over 50 (You better believe there’s stretch!):

Diane von Furstenberg Kara Floral Pencil Skirt

Diane von Furstenberg, Kara Floral Pencil Skirt, $298

Available in Sizes 0-14

Diane von Furstenberg Kara Skirt

Diane von Furstenberg Kara Skirt, $298

Available in Sizes 0-14

BOSS Vedani Windowpane Check Long Pencil Skirt

BOSS, Vedani Windowpane Check Long Pencil Skirt, $278

Available in Sizes 0-14

BOSS Colorblock Ponte Skirt

BOSS, Colorblock Ponte Skirt, $278

Available in Sizes 0-14

Black Halo Pencil Skirt

Black Halo, High Waisted, Belted Pencil Skirt, $230

Available in Sizes 0-14 | 3 colors

Spanx Faux Leather Pencil Skirt

Spanx, Faux Leather Pencil Skirt, $118

Available in Sizes XS-3X

JCrew No. 2 Pencil Skirt in Bi-stretch Cotton

J.Crew, No. 2 Pencil Skirt in Bi-stretch Cotton, $80

Available in Regular, Petite and Tall | Sizes 00-24 | 5 colors

Vince Camuto, Long Fitted Skirt, $69

Sizes XS-XL

Express High Waisted Pencil Skirt

Express, High Waisted Extreme Stretch Pencil Skirt, $60

Available in Regular, and Petite | Sizes 00-18

Ellen Tracy Womens Pencil Skirt

Ellen Tracy Women’s Pencil Skirt, $55

Available in Sizes XS-XL

Top Ten Pencil Skirts for women over 50


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