Wednesday 6th July 2022
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In which I argue that pencil skirts are wearable

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.

Posted on February 1st, 2018 38 Comments

38 Responses

  1. Ljchicago says:

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

  2. Christina says:

    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.

    • y.k. says:

      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.

      • Katrina says:

        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.

      • Jennifer says:

        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.

    • Heather says:

      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.

  3. rockfox says:

    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.

    • Marissa says:

      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.

    • Barbara says:

      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.

  4. y.k. says:

    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.

  5. Caroline says:

    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.

  6. themis says:

    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.

    • Nicole says:

      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.

  7. Maryse says:

    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.

    • Maryse says:

      V-neck sweater.

      • Keirele says:

        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).

  8. c.w. says:

    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?!?!?

  9. Katrina says:

    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.

  10. S says:

    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.

  11. Mimi says:

    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.

  12. Eloise says:

    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.

  13. Amy in StL says:

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

  14. Francine says:

    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 🙂

  15. GT says:

    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!

  16. Francine says:

    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!

  17. Mary Alice says:

    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?

  18. Lorange says:

    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.

  19. Mamavalveeta03 says:

    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!

    • rockfox says:

      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).

  20. Wendela says:

    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!

  21. Tiffany says:

    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.

  22. Maggie says:

    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.

    • Monica M says:

      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.

  23. Graygrrrl says:

    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!

  24. moi says:

    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.