Pencil It In | Working the Pencil Skirt into Your Work Attire, Including 25 Examples with Do's and Don'ts

Starting this week, every Wednesday on The Lovely Side will be devoted to wardrobe, hair, and beauty content.  With summer internships right around the corner and interviews for real world jobs looming as well, I thought now would be a good time to delve into the world of office fashion.  

Sarah, a reader, recently emailed me asking about how to style a pencil skirt for her "somewhat casual, somewhat professional workplace full of fashionable co-workers."  She's been lusting after pencil skirts at several stores, but been hesitant to purchase one for fear of looking bad in it and not knowing what to wear with it. 

Well, Sarah, the good news is that pencil skirts are super flattering on most body types.  You just need to get the fit, style, material, and closure that best suits your body.  Always, always, always try pencil skirts on in the store.  Sizes will vary by fabric.  Walk around, bend over, and sit down in the skirt to test how comfortable it is.  The right skirt should hug your curves and smooth your silhouette, not squeeze anything into unsightly lumps.  It should be comfortable and flexible, too.  The perfect pencil skirt will very possibly end up being your most favorite, most comfortable, go-to piece of office attire.  

I'm a big fan of pencil skirts myself and will wear one every chance I get.  While I dress them down from time to time, my favorite time and place for a pencil skirt is an interview or workday.  Here are some of the ways I wear my pencil skirts:  (Note that these are not the exact pieces of clothing I own, just very similar  lookalike pieces I scrounged up online.)

My all-time favorite pencil skirt is a bright golden yellow one with a high waist that hits right at the knee.  It elongates my legs when something is tucked into it.  And it smooths out my curvy waist when shirts are worn over it.  Yellow is a great color to wear to an interview since it gives off positive vibes.  I like to pair it with a rich teal cardigan and coral pumps for a fresh, off-kilter take on primary colors.  To ground the outfit and keep it from getting too rainbow-dashery, I throw in a white tank and brown leather accessories.  When wearing so much color to an interview or to the office, less is more when it comes to the rest.  Skip the busy patterns.  Exclude fussy accessories and jewelry.  The color speaks for itself, so simplicity is key.

I have a bright chartreuse skirt just like my yellow one.  I've found the yellow-green color can be more difficult to pair with colors.  With coral or pink, it feels too watermelon-y.  With red, we're getting into Mrs. Claus territory.  A bright, trendy hue calls for more subdued surroundings so that it can take center-stage.  So I pull out the neutrals.  Since the green is so vibrant and modern, I like to soften it up with an ivory lace tank.  Then to tone down the frilly femininity, I balance it out with a charcoal gray boyfriend blazer.  Since the skirt elongates my legs, a pair of nude pumps are perfect.  Simple nude accessories complete the fresh, springy office look.

Springtime puts me in the mood for pastels and hot pink, but these colors can be especially tricky when trying to bring them into the workplace.  Pastels can come off as childish and hot pink can scream Legally Blonde even if you're a brunette or redhead.  The best way I've found to wear these colors together in a professional getup means bringing them back down to earth with neutral tones.  But black can be so dark and white can be so, well, light.  So in with the gray, beige, and even better yet... greige!  My grayish brown skirt is second in my heart only to the yellow one.  It can look gray or light brown depending on what I wear it with.  It works perfectly with a lovely mint blouse I recently purchased, my beloved brown t-strap pumps, a hot pink belt, and cream cardigan.  Simple accessories and a tinge of pink lipstick makes this a lovely and very ladylike look to don at the office.

If your internship, job, or interviewing company leans toward the casual side, you're lucky enough to be able to integrate the chambray trend into your workplace wardrobe.  Leave the faded, light-wash, distressed, and patterned denim shirts to the weekends.  A dark denim chambray blouse will work best in a professional environment on the casual end of things.  I like to tuck mine into a beige pencil skirt and slip into camel-hued leather flats for a pulled-together, effortlessly chic, casual career look.  The outfit just seems to call out for a few pops of gold and red, too.

I have several black pencil skirts, but I tend to wear them more in the winter.  Once springtime hits, they barely see the light of day.  But if you're interviewing or working at a very corporate place, you'll want to look your utmost professional.  Time to bring in the black.  Bonus for the fact that black is super slimming and you'll look killer in a chic black pencil skirt.  I like to wear mine with a neutral beige and black, tiny polka-dotted print blouse and timeless black pumps.  But with a classic black pencil skirt, almost anything goes.

Now enough about me and how I prefer to wear my pencil skirts... let's take a look at some real life examples.  

1: Non-fussy floral pencil skirt + chambray shirt + brown leather belt + statement necklace.

2: Nautical striped pencil skirt + hot pink blazer + plain white t-shirt + gold boyfriend watch.

3. Black and white polka dot pencil skirt + teal blouse + black peep-toe pumps + gold jewelry.

4. Emerald green pencil skirt + casual striped rugby shirt + brown leather belt + boyfriend watch.

1. Bright coral pencil skirt + polka dotted teal and white blouse + dark brown belt.

2. Lacy pink pencil skirt + ivory button down + nude peep toes + statement necklace.

3. Khaki pencil skirt + navy and white striped shirt + red belt + red pumps + hairband.

4. Mustard hued pencil skirt + navy and white polka dot blouse + belt + nude pumps. 

1. Black pencil skirt + plaid button down + olive cardigan + thick brown belt + black pumps.

2. Ivory pencil skirt + denim chambray top + black metallic-tipped heels + simple chic clutch.

3. Fuchsia pink pencil skirt + cream tank + tan cardigan + brown belt + orange-toe nude heels.

4. Tan, textured pencil skirt + light blue oxford shirt + black strappy heels + camel leather clutch.

And, of course, I can't end this post without several NO WAYs

when it comes to wearing your pencil skirt in a professional environment.

1. Pencil skirts already hug your curves, so keep the length at the knees to keep it office friendly.  Also, keep your shirt on.  Shoulder, cleavage, etc. should be covered up.   Neon colors, off-the-shoulder tops, and thigh-high hemlines are meant for weekends, clubs, and in this case... the Jersey Shore. Keep it classy, ladies.

2. Red is a bold color for an interview or the workplace.  While it can express assertive, it can often do more damage than good... especially in heavy doses.  Red can have the same effect as a stop sign, urging future employers STOP! and proceed with caution before bringing you aboard.  Red can also be too sexy for the office.  And it can be downright skanky when worn with animal print, but more on that later...

3. While this lady may be a fashionista in her own right, she's a walking mannequin with two blaring errors that shouldn't enter the boardroom... or the front door of any business.  Let's start from the ground up.  Such strappy shoes are too sexy and frankly too painful for work.  Leather and high, thigh-revealing slits have their place bed, errr, uh... bar hopping, not hopping up the corporate ladder.  So if you want to dominate that interview or board meeting, forgo the dominatrix garb.  Her neckline, statement necklace, and even floral jacket are passable.  

4. Mixing and matching can be a fun way to let your personality and chic style shine through... only if you know how to do it right.  While stripes aren't so bad, these stripes paired with this animal print is horrendous.  Oh yes, about that animal print.  Save for maybe wearing a chic animal print belt or hairband to an ultra-on-trend office in the fashion or PR industry, there's really no place for cheetah/leopard/zebra/giraffe/wild thang patterns at the workplace.  It's too difficult to pull off and too easy to look downright trashy.