It’s not uncommon to stumble upon a basic black pencil skirt in the professional woman’s closet.  It’s an easy, fail-safe piece that will likely never go out of style.  When I was a working woman who didn’t work for myself and also wore black, I always had multiple black pencil skirts in varying lengths.  Like a basic pair of black tailored pants, it’s hard to mess up a basic black pencil skirt.  However, because of their ease of wear, it’s also very easy to fall into a rut when wearing one.  If you have a basic black pencil skirt in your wardrobe and have found yourself on autopilot when putting outfits together, today’s post will give you some fresh ideas.

Five Ways to Wear a Black Pencil Skirt

Before we get into the looks here are some quick general tips on pencil skirts

  • Pencil skirts are typically more flattering on the body when they peg or taper a bit at the hem vs. fall straight from the hip.  The tapering works with the natural curves of the body whereas a straight pencil skirt that doesn’t taper can look like a box.  Keep in mind this taper doesn’t have to be major, even 3/4″ of an inch can make a difference.  This is also an easy alteration that can be done if your pencil skirt doesn’t taper.
  • The perfect length of pencil skirts are typically right above or right below the knee before the curve of the calves.  Beware of pencil skirts that are hemmed at the widest part of the calves.  The length will make your legs look heavier than they are.
  • The biggest caveat of pencil skirts is they typically require heels to look proportionate and balanced on the body.  If you prefer flats, opt for shorter pencil skirts, hemmed to right above the knees or shorter if appropriate.  Keep in mind, however, pencil skirts do not require sky high heels to look right.  Even a small heel will make a difference.  Longer pencil skirts usually require a higher heel.
  • Overall balance is achieved by considering the lengths of the tops and jackets worn with them.  Longer tops and jackets typically look better with shorter pencil skirts and longer pencil skirts often look great with shorter tops and jackets.  A tunic and midi length pencil skirts is usually only passable on those who are quite tall or are wearing higher heels to create a balanced proportion.

Okay, let’s get to some looks.  I styled these outfits using this basic wool pencil skirt from Theory.  For more black pencil skirts, check out the end of this post.

Outfit #1

black pencil skirt

With suited separates becoming more popular than suits in corporate environments, a black pencil skirt can be a very helpful piece to have in your wardrobe.  In the outfit above, I styled a Boden blazer with a L.K. Bennett tank underneath.  I finished the look with a teal work tote from Dagne Dover, delicate station necklace from Nadri and printed pumps from Sam Edelman.

Outfit #2

black pencil skirt

Next up, this sleeker way to wear a black pencil skirt.  Personally, I love the way beige and tan accessories look with an all black look, but you can certainly swap out the accessories I chose in this outfit for black ones.  I styled the black pencil skirt with a slim Topshop turtleneck sweater and finished the look with tan heeled sandals from Vince Camuto, beige bag from Coach and drop earrings from Stella & Dot.

Outfit #3

black pencil skirt
This next outfit I styled using a tailored top from BOSS Hugo Boss. A few of my clients have similar versions of this top in their wardrobes and what they like about them is how they are tops that don’t require layering pieces to look finished.  Giving this outfit an edgier look, I finished it with a pair of black booties (that can be worn with opaque tights), a statement necklace from BCBG and cobalt bag from Danielle Nicole.

Outfit #4

black pencil skirt

I threw in a pop of soft blue to this rich black pencil skirt work look.  I layered the very popular Nic + Zoe 4-way cardigan over a cowl top from MM. Lafleur in the Birch shade.  Finishing the outfit, I used these blue low heel block heel pumps from Sole Society (that one of my clients call the most comfortable shoes shoe owns), a burgundy handbag from Vince Camuto and blush drop earrings from Kendra Scott.

Outfit #5

black pencil skirt

Black pencil skirts in classic wool fabrics are typically best for work.  With a little finagling they can sometimes be worn for non-work events.  I styled this black pencil skirt more casually using an off the shoulder top from Banana Republic, kitten heel sandals in grey from Nine West, clutch from Botkier and long pendant in silver.

Shop for black pencil skirts

If you don’t own one already, here are some more black pencil skirts to shop for.