In which I argue that pencil skirts are wearable

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pencil skirt street style

I know the general impression is that pencil skirts look best on those who are long and lean, but I love the way they look on a woman with curves—very sexy and confident. I find that full skirts, with all their volume, tend to make me look bigger, and that a pencil silhouette can actually be on the slimming side. And I like how the woman here is wearing hers with a big slouchy sweater, which is so chic and also nicely casual (yes, I know her shoes tell another story).

lou lou skirt

The trim at the hem of this skirt from Tibi is such a nice hit of femininity, and I love that it’s asymmetrical.

max mara skirt

A denim pencil skirt  with a super-clean wash, which isn’t the easiest thing to find (I like this one from AG as well).

allude skirt

This one is ribbed cashmere, which would be so cozy to wear right about now.

mango skirt

Look closely at this check print and you’ll see that it’s a pretty great green-and-white pattern.

& other stories skirt

I am crazy for this asymmetrical leather choice from & Other Stories. It’s not cheap, but it’s pretty well-priced for a leather skirt.

 

universal standard skirt

And here’s a faux-leather option from Universal Standard (here’s another—quite well-priced—similar choice).

karen millen skirt

And another faux leather—this one in a pretty magnificent blue.

j crew pencil skirt

A nice simple grey option from J. Crew that’d be endlessly versatile

halogen pencil skirt

And here is a very reasonably-priced option.

camuto pencil skirt

I like the side slit here, and the fact that it, too, is well-priced.

theory skirt

I’m pretty sure I showed you this gorgeous ruched skirt from Theory before, but it’s nicely marked down now. It’s got a very forgiving cut.

whistles pencil skirt

This leather skirt also comes in a very nice burgundy hue.

standards & practices skirt

The lace overlay here is so lovely and sweet: I’d dress it down with a simple white tee.

milly pencil skirt

A sequined skirt is perfect for a party (and here is a pretty stupendous green sequined choice in extended sizes).

And in case you missed it: here is a post I did on black skirts a while back.

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Comments

38 Thoughts on In which I argue that pencil skirts are wearable
    Ljchicago
    1 Feb 2018
    7:43am

    I totally agree with this. I have several pencil skirts with stretch and I think they look great on this short body with hips!

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    Christina
    1 Feb 2018
    7:51am

    Anyone have any shoe advice for these? I always get tripped up, especially in the winter with what (non-heel) shoe to wear with pencil skirts.

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      y.k.
      1 Feb 2018
      7:59am

      i agree. hard to imagine a flat shoe that would go with this skirt style. they all cry out for a knee high boot. well, i know many would pair w/ an ankle boot but that seems to break up the line.

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        Katrina
        1 Feb 2018
        9:57am

        An ankle boot with a low, chunky stacked heel? I’m thinking a low-heeled Chelsea type boot. A black boot with black tights sounds chic to me and going all black would ideally not break up the line of the leg.

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        Jennifer
        1 Feb 2018
        10:17am

        I wear pencil skirts several times per week and the footwear is definitely tricky in the winter. My solution is a pointed-toe black ankle boot, plus black tights, similar to what Katrina’s proposing. But I think any pointed-toe shoe to elongate the line of the leg would be a good option. If you want a flat, perhaps a stylish black pointed loafer with a lug sole, if such a thing exists? With a long coat that falls past the hem of the skirt this combination could work well.

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      Heather
      1 Feb 2018
      10:45am

      If it helps at all, I keep a pair of shoes in my office and wear snow boots to and from. I’m a big skirt-wearer, even in the winter, as I can’t find dress pants that fit to save my life.

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    rockfox
    1 Feb 2018
    7:57am

    Plus size woman chiming in – pencil skirts are awesome. I have a tummy that made me avoid them in the past. I’ve found that wearing something with a bit of a peplum on top (a style I normally don’t like) is the key. It hides the tummy but keeps the hourglass shape that you want with a pencil skirt. I think the best plus size pencil skirt is Eloquii’s neoprene skirt. The material is thick enough to skim over any lumps and bulges but it is still cut close to the body (nothing worse than a pencil skirt cut too wide). Tons of colors and patterns too.

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      Marissa
      1 Feb 2018
      9:03am

      Ditto. Curvy girl here and a pencil skirt with a slightly high waist is very flattering and always looks chic. The trick is top has to hit at the right spot just above the hip to not hide your waist. I keep trying to tuck shirts in but usually it accentuates my large bust in a way I don’t like, not enough torso between the boobs and the waistline.

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      Barbara
      1 Feb 2018
      2:22pm

      Me, too (oh, what a different Me Too that is!) I own the Universal Standard one and while it’s a little on the long side, I still adore it, especially with a half-tucked three quarter sleeve tee shirt. In fact, I think I’ll wear that tonight.

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    y.k.
    1 Feb 2018
    8:00am

    i agree. hard to imagine a flat shoe that would go with this skirt style. they all cry out for a knee high boot. well, i know many would pair w/ an ankle boot but that seems to break up the line.

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      y.k.
      1 Feb 2018
      8:00am

      whoops!

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    Caroline
    1 Feb 2018
    8:45am

    Yes, totally agree!
    Weather permitting l like to wear a pencil skirt with higher clogs.
    Thats the closest I get to wearing heels though…
    Lady heels are pretty but they’re just not me.

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    themis
    1 Feb 2018
    8:47am

    I’m a petite with curves, except my waist is straight, and they just don’t work on me – turn me short and squat and square. I mean, I have tried and I keep trying, but the mirrors don’t lie; the proportions are not flattering. If I’m in a skirt, shorter and a-line gives me a waist and long legs.

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      Nicole
      2 Feb 2018
      9:21am

      Same exact. I’m very straight up and down and I end up with a boxy situation. But man, I tried for YEARS. I adore the look. I have owned so many pencil skirts. These days I am all about the high waisted skirt, with a shirt tucked in.

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    Maryse
    1 Feb 2018
    9:27am

    I prefer an a-line shape but I do like wearing a dark stretchy pencil skirt (a non stretchy skirt would require too many alterations) with a slouchy neck sweater or top. And I’ll wear it with doc marten oxfords or sneakers. A high heel isn’t me. It’s really all about proportion and what feels like you.

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      Maryse
      1 Feb 2018
      9:29am

      V-neck sweater.

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        Keirele
        1 Feb 2018
        1:25pm

        Totally agree! I have a stretchy one that I wear with black frye ankle boots. I think the key is to keep the lower half all in a similar, neutral, color family (and to walk with confidence, which I firmly believe makes almost any outfit flattering).

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    c.w.
    1 Feb 2018
    9:40am

    Totally agree with everyone here––pencil skirts are great on a curvy body. I have a difficult time with skirts in general because I have a “column” body––not a lot of difference between waist and hips––but, the one skirt I can sometimes make work on my body is a pencil skirt.

    You pulled out some excellent choices, Kim!

    Why is it I’m so drawn to sequins these days?!?!?

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    Katrina
    1 Feb 2018
    9:54am

    That image has been on my Pinterest for ages. I love the combination of the sleek skirt and the oversized chunky knit. Outfits like that make me wish we had four seasons where I live.

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    S
    1 Feb 2018
    10:32am

    I used to wear pencil skirts almost exclusively when I was a couple of sizes smaller (every color J. Crew made of one that had a very flattering thick band at the top), but I just can’t find anything that looks good now. I’m 5’7″ and size 8 or 10 but carry wight in my belly (flat butt, small chest) and every pencil skirt I try in various sizes just highlights that area. I love the look of the slouchy top with the sleek skirt, but for me, without heels and a fitted tucked in shirt, I feel like I look like a big blob.

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    Mimi
    1 Feb 2018
    10:34am

    On the shoe question – in winter I’ve worn a pencil skirt with a square toed, high block heeled loafer-type shoe and tights. A pointy toed ghillie with a 2 1/2″ heel works with tights too.

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    Eloise
    1 Feb 2018
    10:40am

    I’m pretty sure it’s just me, but I can’t wear pencil skirts. My stride/gait is too wide/long or something and I end up ripping them. I love the look, though.

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      Mamavalveeta03
      1 Feb 2018
      6:08pm

      Power walk, Eloise!

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    Amy in StL
    1 Feb 2018
    11:24am

    A cashmere pencil skirt? I might never take it off, I love cashmere everything this time of year.

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    Francine
    1 Feb 2018
    1:12pm

    I adore all of these!

    I’m such a fan of pencil skirts (especially when they are past the knee). They are extra flattering when you have a little extra!

    I wish I had places to go and I’d wear mine more often 🙂

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    GT
    1 Feb 2018
    1:38pm

    I wear pencil skirts all the time: and I am VERY short but find they work well. And as for sequins, I bought a beautiful ombre burgundy sequined pencil skirt a couple of weeks ago for *really* cheap (it was right after New Year’s so was drastically reduced). I just wore it to the office with an Oxford shirt and a sweater : yup, right in brought daylight. Got a lot of compliments; it was comfortable. I suggest you give it a try!

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    Francine
    1 Feb 2018
    2:33pm

    Ok, so this inspired me this morning. I pulled out a knit pencil skirt (new, from Zara), black turtleneck, tights…Did my hair, put on some makeup, earring, the whole shebang. (Mind you, I run my business through a home office. I always get dressed up, because I love clothes! BUT, not skirts/dresses at home.) Came downstairs. The husband (who also works at home), said “You look great. Ya got traffic court or something?” (‘Working Girl’ reference for those under 45).

    Anyhow, I’m gonna look awesome for school pickup!

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    Mary Alice
    1 Feb 2018
    5:22pm

    Kim, could you weigh in on the shoe question? I have pencil skirts that sit in the closet because I so rarely feel like wearing heels; and boots are not an option in warmer weather. Are flats ok?

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      KimFrance
      1 Feb 2018
      5:50pm

      I think flats can look adorable with pencil skirts—I like them best pointy.

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    Lorange
    1 Feb 2018
    5:37pm

    I also love pencil skirts! I just scored a black ponte knit Eileen Fisher pencil skirt from Nordstrom Rack and it is great. I can tell I will wear it a ton.

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    Mamavalveeta03
    1 Feb 2018
    6:03pm

    Pencil shirts look great on a woman with hips and a butt. Very Jessica Rabbit or Mad Men.

    The leather one by & other stories is almost architectural. Gorgeous!

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      rockfox
      1 Feb 2018
      9:48pm

      I’ve recently re-entered the dating world and pencil skirts with heels are my fave for days when I have a date after work. Professional enough for the office, but since I have hips and a butt they are still very sexy for a date. I’ve had more than one Mad Men compliment (might also be because of the red hair).

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    Wendela
    1 Feb 2018
    7:28pm

    I adore that denim one but it’s out of my price range (darn you, Max Mara!). The AG one is too short for the look I’m aiming for. Can you let us know if you ever find a (more affordable) dark wash, long, denim pencil skirt? I would love to find that. Otherwise, good list, and I totally agree!

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    Tiffany
    1 Feb 2018
    7:30pm

    Love pencil skirts – have a beautiful burgundy leather one and a black faux leather one and they both get a lot of wear every winter.

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    Maggie
    2 Feb 2018
    1:01am

    As a small-waisted, big-hipped girl, pencil skirts always ride up on me when I walk, so I think they’re cute but so annoying. I have a great denim skirt that I find myself constantly tugging on.

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      Monica M
      7 Feb 2018
      5:29pm

      Same here. I have a rear that pops out quite significantly from my small-ish waist. I find that any pencil skirt pulls across my tummy quite uncomfortably because my rear takes up so much space. And the riding up…super annoying! I used to be able to wear one and did frequently but the further I get past 40 the pencil skirts get pushed further to the back of the closet.

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    Graygrrrl
    2 Feb 2018
    4:16am

    I totally agree! I love pencil skirts because they van be formal or work. I love to pair mine with a band tee or other graphic tee fur a fun casual look!

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    moi
    5 Feb 2018
    8:33am

    That’s pretty much my problem as well. But, like Kim, full skirts just make me look wide (the money I wasted over the years trying to make them work!) I have to hit something in between, which usually means a sleek A-line in a relatively heavy fabric, which stays close to my body at the waist and hips, or a silky wrap skirt. But, in the end, I don’t wear many skirts, LOL. Dresses work much better on me.

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Kim France

I was born in Houston, Texas in 1964 and have lived in New York City since 1988. I had a long career in magazines, working at Sassy, Elle, New York, and Spin, and in 2000, I founded Lucky magazine, which I edited for ten years.

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