Business Casual Superstar: The Timeless Pencil Skirt

by Rachel Yeomans | May 13th, 2010   

By Huma Rashid

Hands down,the most classic and timeless and flattering piece for everyday wear in a woman’s work wardrobe is the pencil skirt. This elegant article was actually created by Christian Dior in the 1940s, after the second World War. So, okay, fine, I guess there is somewhat of a timeline attached to it. You guys caught me. But still! We’re going to call it timeless anyway!

Pencil skirts are just the best. They create such a flattering, womanly silhouette and instantly polish up any outfit. They’re vintage-y in their own right (how many of you watch Mad Men? You can’t throw a cigar on that show without hitting a pencil skirt!), but have been successfully updated over and over throughout our trend cycles, which is why you can wear them to work tomorrow without looking like you’re one of Don Draper’s rejects that’s just having a really hard time letting go.

Anyway, enough of the Mad Men jokes.

Today, I decided to share a couple of interesting pencil skirts, all of which I like for different reasons. Pencil skirts look so classy and sexy with high pencil heels, and magically manage to look dressed down with chunkier, stacked heels. For heavier fabrics, like a pencil skirt made out of tweed (oh, man, my heart actually fluttered at that), go with a nice, solid, round-toe pump. This will emphasize the rounded shape of your calves. That works with any pencil skirt, really, but I think it plays particularly well when the skirt is made of a heavier, thicker fabric.

So let’s see what I managed to pull out of my magic hat today. As always, click to purchase.

1 Business Casual Superstar: The Timeless Pencil Skirt


This is just a fun, bright look for summer. You know how it goes: the weather gets warmer, the flowers come out, the days get longer, and everything about your mood just improves. And for me, that translates into wanting to wear bright colors and florals. I’m wearing a floral tee right now! Imagine that. Anyway, this is a great way to add color and florals to your office look. To keep from looking too matchy-matchy, or like your mother dressed you for your second grade school picture (I remember a hideous banded, beaded turquoise dress with tights that my mother made me wear – horrible! Make it stop! Aaa!), I’d pair this with a white or cream blouse, button-down for a more professional look, or billowy and tunic-y, tucked into the band of the skirt, if you want your office style to gravitate toward a freer, more boho kind of look. Remember, you can still play up your style, whatever it is (edgy, old-school/vintage, punk, bohemian), in your work clothes. You just have to remember to balance it out. So, like I said, I’d probably pair this with a billowy (or buttoned) white or cream blouse, a nice but understated necklace (read: in one color, not multiple), and a pair of black peep-toes.

2 Business Casual Superstar: The Timeless Pencil Skirt


This one from Ann Taylor is just adorable! A little on the short side, at least, for me. I’d have preferred it at least an inch or two longer. But if your office is a little less conservative, it might work. Again, I have no way of knowing: each office defines business-casual differently. Your best way of knowing what you can and can’t wear in terms of business-casual clothing is to look at your co-workers and your boss for cues.

Length aside, I like this one for its use of color and the interesting pattern. I didn’t think I’d like the little amoeba-like images, but I do! They’re not totally amoeba-like, though, so that’s probably it. Amoebas freak me out. You know what I’m talking about – I think it’s called a paisley print? I call it amoeba print. It’s scary.

Since the skirt works with white, black, and gray, I’d be tempted to pick a really nice dark berry button down to go with it, which would give me a lot of freedom with the shoes, too! I could go with black shoes, gray shoes, black shoes with white accents, or something in the purple shade family. So many choices!

3 Business Casual Superstar: The Timeless Pencil Skirt


This one is from White House | Black Market, so that explains the color scheme. I am usually very careful with floral prints; the space between the flowers can either make or break the look. Not enough space and it’s gaudy and too busy; too much space and it looks disorganized and half-baked. But if there’s very little space and the print is small, it’ll work. Lots of little caveats that have to go into the decision. This is why buying floral prints is so stressful!

But this one didn’t stress me out all that much. The color scheme keeps it from looking as busy and overwhelming as it would if it was brightly colored, and there’s a good amount of space between the flowers and vines that makes it look evenly arranged and cohesive. It’s a solid choice, and the white makes it a great summer piece. I might wear this with conservative black pumps and a really bright, vibrant, deep blue button down, because black and white make blue pop so well. It’s why girls with dark brown or almost-black eyes need to wear navy blue eyeliner – the whole popping thing we just discussed. These are facts.

4 Business Casual Superstar: The Timeless Pencil Skirt


This lovely number comes to us from Lord & Taylor. I apologize for the low-quality image; the larger one wouldn’t load properly so I had to resize the thumbnail and adjust it the best I could. But that doesn’t change how lovely this banded skirt is, and that price is offered at steep mark-downs. You’re welcome!

5 Business Casual Superstar: The Timeless Pencil Skirt


This one is from the Gap, and I like the band on top and the clean construction. It’s just a simple, no-fuss, functional pencil skirt. I can’t use the word ‘functional’ anymore without thinking of the conceptual separability test in Copyrights; this is what law school does to your brain. Run far away, folks. I picked the khaki color over black (the other selection) because we all have black pencil skirts. Time to mix things up a little with khaki! It opens up so many new color options! Well, okay, that’s a bad example, because black is basically the Switzerland of colors and works with everything, even its arch-frenemy, brown. But you must agree that the same color, when worn with brown, looks different and, more importantly, makes you look differently when worn with a nice khaki color.

6 Business Casual Superstar: The Timeless Pencil Skirt


I’m including this because, in my sheltered little life, I’ve never seen a pencil skirt with suspenders attached. But some of you ladies are quite darling little hipsters, and this is a way to incorporate that into your work wardrobe without taking it too far.

7 Business Casual Superstar: The Timeless Pencil Skirt


This is my favorite one in the whole list, I think. Look at that vivid blue! As if a pencil skirt wasn’t flattering enough on its own, the designer decided to put that bright blue panel down the front, surrounded by black, because those colored panels in the middle lengthen the body for a nice lean look, and the black on both sides slims the silhouette because it tricks your eyes into thinking that your body ends closer to the brightly colored panel than it actually does.

And the outfit on the model in this case is perfect. I’d wear it with a nice black sweater and a pair of awesome black heels, probably with some silver jewelry.

And there we have some lovely pencil skirts for you ladies to wear in to work!

Suede Pumps
Suede Pumps

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