Fall’s here and for me, there’s nothing quite as snappy on the autumn fashion parade as the perennial pencil skirt. It’s been a hit for decades (since WWII gals had to abbreviate their skirts to satisfy fabric rationing needs) and happily, almost every Star Style can rock one. (Not sure what your Star Style category is? Click here to take the quiz, then hurry back! PS: That’s Doris Day below!).
Today, I’m making a case for pencils by showing you how some of Hollywood’s hotties have made that skirt their own and learning the how-tos of wearing this simple but sophisticated basic. Then, we’ll look at the current crop to find the pencil skirt that will be the workhorse of your work-a-day wardrobe.
Pencil Skirt Primer
Not all pencil skirts are equal; some are shoddy, some are skimpy, some are frumpy. After you’ve found a great pencil skirt, you’ve got to befriend it. Let’s get started!
First and foremost, get the decade right. Yes, pencil skirts are timeless, but how you wear one can peg you as either fashionable or freaky. Yes, I know you want to look just like Katharine Hepburn in WOMAN OF THE YEAR…
…or Lauren Bacall in HOW TO MARRY A MILLIONAIRE (god knows I wave off that temptation daily!), but that knockout combination of booty-hugging sheath skirt and super-fitted, shoulder-focused blazer is not *quite* back yet. More’s the pity.
The 80s were jam-packed with that Adrian-inspired shoulder; Donna Karan and Norma Kamali were the synchronized shoulder sisters back then. Hang in there, though, it might happen again in our lifetimes.
Flip through up-to-date catalogs and magazines and get on-trend, for your own sake. Overtly costumey attire at the office translates to: “I hate working here and nuts to you.” Or “I don’t know where you are, buster, but I’m at the party in my head.” It’s giving the sartorial finger to your boss, essentially.
Get the fabrication right
Pencil skirts are popular right now (face it, a version of them is always “in”), so there are a lot of cheap ones out there at places like (no offence) Sears or Penney’s, H&M, or New York & Co. Now, I shop at these places, but I’m telling you, a pencil skirt NEEDS a certain amount of firmness and structure, and the cheaply woven, cut-rate material that allows that skirt to sell for $16.99 is not going to cut it. That skirt will wrinkle in VERY unflattering places, pull across your tummy. The side seams will twist like a canyon trail, the hem will wave and buckle and you will be one unhappy girl after the first wearing or cleaning.
Since pencil skirts are sooo timeless, consider them an investment. The finest-made examples I’ve ever encountered at a very reasonable price of around $100 are at J.Crew, who has pretty much cornered the market on dependable, well-designed and executed pencil skirts.
They have average, tall and petite sizes, and a bevy of gorgeous colors, patterns, and fabrics; all downright yummy. You’ll want them all, but invest in neutrals first if you start collecting (navy, grey, black, camel, brown. Or, what the hell, buy one in pumpkin orange and blaze a trail). Each version is crafted well of truly fine materials; double-serge cotton or wool, including a professional-grade “Super 120” merino wool (the number indicates thread count; 120 is an exceptional quality with a sheeny finish and a smooth hand).
Amazingly, these skirts are lined with stretch-kissed satiny polyester for give and comfort. Couture for the masses! Slimline waistbands sit a tad below the waist, so they are comfortable for all-day wear.
Okay, I know this is turning into an ad for J.Crew, but I can’t help it. I’ve looked for YEARS for quality pencils that fit me and now I’m dancing around like Cyd Charisse in these snazzy snug-not-slutty skirts.
Get the foundation right
Speaking of Cyd, unless you have legs and hips like hers honed by years of self-discipline, diet, and dance, you’re going to need a foundation garment of some sort. Go find a nice lady in the lingerie department of your favorite store and ask for her help. Be prepared to be shocked at how different your body is going to look with a little assist.
Wear (or bring) your shaper when you go shopping—the skirt will fit entirely differently.
Spanx is the gold standard of shapewear and they’ve got some helpful stretchy long-line shapers that supply the slink of Cyd or the oomph of Marilyn without the dieting and exercise. Not that you should skip that, of course! See for yourself below. Painful, ain’t it?
Now I have to say that for many, the return of control-top pantyhose, after years of the ridiculousness of knobby, vein-y bare legs (in snowy climates, for goodness sake!) is a welcome one and some of you will be able to wear pencils with a great pair of pantyhose or tights and a half-slip (yes. I mean that.) and call it a day. However, please check your rearview before you exit. Every pencil needs an eraser.
Get the hemline right
There’s a fine line between the perfect hemline and something that will have you fidgeting all day long and putting file folders on your lap to keep from feeling like Sharon Stone.
If you’re over 40, the perfect standing length is just below your kneecap. I know, “but Diane Sawyer; but Barbara Walters,” yes, yes, yes. See Exhibit A below. Diane has GREAT legs, no doubt, but the knees are past their prime(time). For me, bare legs in a business situation, for women of a certain age, is the equivalent of going out without makeup. If you insist, at least give yourself some ogle-worthy gams–take some L.A. legs lessons from GlamAmor.com’s Kimberly here.
So, unless you live in LA or NYC, a short, slim-fitting pencil skirt walks the tightrope between trendy and tacky. Today’s mode for “correct” pencil skirts hovers near the knee—slightly above or slightly below. Take a look…which legs are the most attractive below?
For most of us, too long a skirt and we look frumpy; those straight-up-and-down pencils from the minimalist Nineties add pounds and make you look like a Church Lady—and not in a good way. Even Joan can’t carry it off. (But, wow, what a difference between a loose jacket and a fitted one on her. Same year, same movie.)
Tip: J. Crew’s new longer-length “Telegraph” pencil skirt runs 27” long, which hits RIGHT at the right-below-the-kneecap sweet spot on tall gals, even ones with freakishly long femurs like me. They also have tall sizes for their basic “No. 2 Pencil Skirts,” which makes me remember them in my prayers. (Here I am in my latest J.Crew pencil–in a color they call Warm Burgundy–in full-on costume, hair, and make-up as “Moneypenny” to introduce FROM RUSSIA WITH LOVE at our beloved Dryden Theater. Note: I would NOT wear this to work as shown, too dated and costumey. I’ll pair it with a skinny turtleneck, color-tinted stockings, and high-heeled oxfords.)
If you’re in your late teens to early thirties, ignore the kneecap rule and shorten the hem a tad to avoid looking mumsy. But, watch your footwear. The basic rule is, the shorter the skirt, the shorter, or more substantial, the heel. Unless you’re layering with leggings, wearing opaque/textured tights or the shoe has a wonderfully chunky platform and heels, brief little minis with spindly stilettos or 5”-inch heels will read “working girl” of another sort and is that what you want?
Get the size right
Remember when fashion editor “Maggie” in FUNNY FACE dictated to Audrey that she needed a “marvelous mouth”? Well, kids, to be happy in a pencil skirt it helps to have a Fabulous Fanny.
The key to that action is FIT! Too loose, the pencil skirt looks baggy at best and dumpy at worst. Too tight and it’s “hey, Sailor, new in town?”
The shape you’re going for is a sharpened No. 2 pencil, not a rectangle of fabric that creates a weight-adding box around your poor unsuspecting legs. If you find a pencil that fits in every other way, only it’s boxy, take it to a tailor to have it “pegged”…this just means that the side seams are narrowed a tad towards the hem—usually no more than 2 inches difference on either side seam. Lana Turner’s skirt has been PEGGED here.
This way, the skirt skims close to the body, not stands away like it’s hating your stockings…which brings us to…
Get the rest of the leg right
The beauty of the pencil skirt is its simplicity, so you can really amp up the footwear and let it take center stage. Smoke ‘em if you got ‘em. This goes back to your Star Style, age, and where you’re wearing the skirt. We’ll get into specifics on that at the end of the post.
Meanwhile, generally speaking:
Younger gals: Try a nice sturdy boot, a buckle-topped skimmer, a ballet flat, a chunky heeled peep-toe or T-strap Mary Jane, wedge, a stacked heel oxford or some outrageous thing, like the Prada flame shoe.
Tights, textured stockings, leggings, bare legs…go for it. Youth is when you can do these sorts of things and be admired rather than whispered about.
Ladies of a certain age: Keep it on the demure side, with a nice platform pump, peep-toes, or chunky sandals or slim-fitting boots. 
Kitten heels, while adorable, can look a bit obvious (Audrey Hepburn lives here). So tread cautiously.
Try stacked heels or beefier ones to add some heft and modernity.
If you go the stiletto route, make sure they’re modernized (like these stunning Pradas below). Hyper-sexy, sky-high pumps can look a bit desperate. Pantyhose, opaque stockings or tights; yes! But please, as mentioned, no bare legs unless you REALLY have got it going on and live in a warm climate. I saw a blue-legged septuagenarian in a pencil-skirt a few weeks ago and while I admired her spirit, her legs were a distraction not an asset, god love her.
Get the top half right
Pencil skirts look so sharp because the line is slim and sleek, so try not to clutter it up with a bulky, floppy top. Choose something simple, classic, and classy.
An overly roomy tunic will look like Lucille Ball pregnant and who wants that (besides, you’ll have a lot of ‘splain’ to do). There are a plenty of options. Let’s start with the tucked-in blouse. 
There’s a reason it’s a classic, but it can be problematic because of the slow-but-steady untucking throughout your day. And, be careful, this look can quickly slide into Trusty Gal Friday…
Fiesty Teacher…
or Bond’s Moneypenny if your hair is too ”done” and you’re wearing classic pumps.
Slim-line pullover or cardigan sweaters are another tried-and-true…
Best bet: one that’s a bit cropped or lanky–in-between will have folks bringing you apples and asking you about the difference between “affect” and “effect.”
If you LOVE your cardigans and want to avoid the “Our Miss Brooks” effect, try criss-crossing your cardi fronts across your bodice (only do this over a skinny tee or top, not a blouse or you’ll be as lumpy as oatmeal). Just layer one side diagonally over the other, straight-jacket fashion, and just tuck in the tails or fasten the exposed one with a stunning brooch. You’ll look like you just lost 10lbs.
Other up-top options that look great: Blouson jackets, peplum tops,
…shrunken schoolboy blazers, long boyfriend cardigans, drapery cardigans, capelets,
narrow turtlenecks. skimmy long-sleeve tees…
and slim-fitting but not tight v-neck sweaters (trying to shy away from the va-va-va-voom Joan Holloway look, of course, at the office).
Statement necklaces, billowy or Hermes-style scarves, and tricky necklines are all great with pencils, as their very plainness focuses the eye upward (unless you are a bombshell and then, the eye is totally bewildered by bounty in all directions).
If you have a long waist, mix it up with a belt. Skinny belts can tie back your blouse or shoe color, wide belts add drama.
Get your posture right
Pencil skirts don’t have to try to be sexy, they bring it. They hug your curves (or sleek-en your angles); they streamline the female form; they show off your legs…but all that is for naught if you slump around in one or let your legs go every which way when sitting. (Virgina Mayo’s got it right, see how Hoagy appreciates her gams?)
Take a stand
Based on years of observation, there are apparently only a few attractive ways to stand when wearing a pencil skirt:
1) Legs in the classic Red Carpet photo pose.
2) Legs crossed to form the perfect vase-shaped silhouette (as does young starlet Nikki Reed here in a leather enlongated pencil..see what I mean about youth?).
You choose. But stand like you mean it, not as if someone just cut your strings.
Have a seat
As for sitting, I’m telling you, your mother was right—legs together like a lady…
(Try to avoid crossing one leg over the other at the knee, like Noel Coward taking tea…that’s murder on your veins). Legs gracefully slanted to one side, ankles tucked neatly as close as possible–Ava’s demure pose is right on the money.
This pose looks ladylike, graceful and surprisingly sexy, attributes most every onlooker appreciates. You only have to see one woman sitting like a stevedore at lunch to know that YOU don’t want to be caught like that. So, ladylike, all the way, gals. My friend Jody at Couture Allure has compiled a dandy tutorial on ladylike sitting; go take a peek. (And while you’re there, maybe she’ll have a nice vintage pencil skirt for you to snap up!)
Your personal pencil
Okay, you may not have Edith Head designing a pencil skirt for you, as she did for Tippi, but now that you’ve mastered the basics (and probably made plans to nip into your nearest J.Crew store to at least try some on), here are a few inspirations and suggestions for each Star Style type’s perfect pencil.
Sophisticated Ingénue
Your free-spirited key principles are youthful, trendy, and funky; stiff, “normal” pencil skirts can look stuffy on you. Romp a bit with accessories, color, and attitude. Hems can be higher or longer and colored or opaque tights for you, or bare legs, but no flesh-toned nylons.
Sensual Bohemian
It’s all about fabrication for your material girls. Sequins, woolens, tapestries, leather or suede, and brocades—then pile on the textured hosiery, exotic accessories.
You can add some length or crop them higher, but watch you don’t slide over into Gypsy Girl Goes Manhattan.
Naturally Charming
Frankly, this is the one Star Style who probably would never want to wear a pencil skirt. By nature, these skirts are confining, and your guidebook reads“comfort and casual,” but if really want to try one, stick to fabrics like cotton, corduroy or suede. Add some boots or flats and comfy tights.
Smartly Tailored
Pencil skirts are you all day long. You can channel your style icon, Kate the Great and rock a pencil skirt daily if you wish. Knee-length and beyond work best, since you tend to watch trends but not give out a skippy vibe. (Again, younger means shorter.)
Stick with killer blouses or shirts in crisp fabrications. Sleek stockings and well-turned pumps, stacked spectators or peep-toe chunky shoes are perfect partners, as are unique blazers with sharp design accents.
Lively Girl-Next-Door
For you, colored pencils! Basically, just go over to J.Crew and you’ll learn everything you need to know. Long or short cardigans and striped tee tops are great ways to break up the boardroom vibe some pencils can give off.
Skinny belts and other preppy touches will make you happy. You and your Boho sister are the only ones who can carry off a bulky sweater, so give it a try!
Classically Ladylike
Silk-blend or pima cotton blouses or sheath tops, luxe, lush cashmere sweaters, long sweater tunics—Grace Kelly at the office is your muse and Chanel is your Top Shop.
Flesh-toned or slightly tinted pantyhose with simple, well-kept shoes. Your favorite heirloom pearls work so well with this clean-lined classic, as does your tank watch. You probably own several pencil skirts already.
Passionate Beauty
Elizabeth Taylor and Marilyn Monroe taught all bombshells how to make a statement with a pencil skirt; peg it to hell and back and team it with a very fitted blouse or sweater. Try a slightly longer sweater that is not tucked in, accented with a skinny belt, like a metallic, at the waist.
Add shoes with some weight to them, not spindly heels, and you’ll modernize the look. Fabric is key for you, too: thin wools and silk-blends are best, even firm double-knits. Never, EVER corduroy, heavy wool, or light-weight printed cottons. Molded is the look for you. Joan Holloway is your go-to gal. Don’t wear a boxy top or you’ve just lost everything you worked for!
Well, that’s the bottom line, gals. When you use the right pencil, you’ll always make the grade. Class dismissed.
(Final screencap, courtesy OutofthePastcfb.blogspot.com)
