10 ways to wear a pencil skirt

You guys! You guys! Did you know you can wear different tops with your black pencil skirt?

I know: mind blown, right? You’re all, “What even is this? HOW did I not know?” And to think you’ve been wearing that ONE top this WHOLE time, just waiting for me to come along and teach you my ways, huh? OK, OK: as with my previous outfits in this series, I’m obviously not exactly providing you with brand new information here, so you can take that as read. I don’t know about you, though, but sometimes the most obvious outfits are the ones I totally forget about, so… how about I just stop rambling now and get on with it? OK, here are some pencil skirt outfits to inspire, or simply pass a few minutes on a Wednesday afternoon…

How to wear a pencil skirt…

50s-inspired outfit featuring black pencil skirt and fitted top

01. With a fitted top

Aaand we’re right in with a retro-inspired look: well, I wouldn’t be me if I didn’t do it, would I? I’m going to try to make sure not ALL of these pencil skirt outfits are retro-inspired ones, but I’m not promising anything, m’kay?

This little sweater was from H&M last year, as was the skirt itself. Neither are currently available on the website, unfortunately, but the good thing about this kind of look is that although I’m calling it “50s-inspired”, the individual pieces are fairly modern, so it shouldn’t be too hard to find similar ones if you want to. Oh, and you’re going to be seeing a fair bit of that belt, I’m afraid: it’s not that I think all pencil skirt outfits require a belt, you understand, it’s just that the skirt is a little bit too big on the waist – whoops. Just pretend you don’t see it: unless you really like it, obviously, in which case don’t bother.

black pencil skirt and strapless top

02. With a strapless t0p

I’m going to have to ask you to overlook the fact that this top is almost exactly the same colour as my skin… and also the fact that it’s not a top at all, it’s a bodysuit. I KNOW. I mean, I have no idea what I was thinking, really. I bought it from ASOS a few years ago, and it was one of those things I bought knowing perfectly well that the chances of me ever wearing it were slim to none, but I just HAD to have it, anyway. Well, what can you do?

Anyway, my point here is that you can totally wear a strapless top (BODY SUIT) with a black pencil skirt. WHO KNEW?

pencil skirt and polka dot halter top

Vivien of Holloway top; Buffalo shoes (old)

03.  With a halter top

Yet another retro-inspired look, and I’ll just take the opportunity here to point out that you don’t actually HAVE to wear your pencil skirt with polka dots at all times. I mean, I do, obviously, but you knew that, didn’t you? There are, however, other types of clothing out there: for instance…

green silk shirt with black pencil skirt and heels

Zara shirt (similar); Moda in Pelle shoes (similar)

04. With a silk shirt

This one’s all kind of, “Lookit me, I’m an important business lady, ready to do some important business!” OK, maybe not: I suspect my blouse is probably a bit too low for the office, but that’s just the kind of rebel I am, you know?

green silk shirt with black pencil skirt and heels

H&M shirt; Dune boots (similar)

05. With a plaid shirt

And now I’m a cowgirl. Yee-haw, people. Yee-freaking-haw.

It’s been at least 2 minutes since I last showed you a retro-inspired look, though, so here you go:

stripe bardot top with pencil skirt

H&M top (similar); Zara shoes (similar)

06. With a bardot top

Oh, come on: AS IF I wasn’t going to show you at least one stripe bardot top! You MUST have known this was coming, surely? And while I’m on the subject of bardot tops, I’m going to sneak in another one, too…

pencil skirt and bardot top

Collectif top; Nina shoes

07. With a slightly different bardot top

This one’s a slightly dressier look: or it would be if I’d bothered to comb my hair, obviously. If you’re looking for something that ISN’T a bardot top, meanwhile…

pencil skirt with slogan sweater

Poppy Lux sweater; New Look ankle boots

8. With a slogan sweater

See also: ‘How to Wear a Slogan Sweater‘. I’ll be sure to link that post back to this one, then you’ll just get stuck in an endless internet loop, going from pencil skirt outfits to slogan sweaters, and back again, over and over… Let’s try to break the loop while we still can, shall we?

pencil skirt and blazer

Zara blazer; Dune heels and clutch

9. With a blazer and heels

I feel like I’d wear this outfit to have important business lunches, which my imaginary secretary would set up for me in between conference calls or something. I would absolutely hate that, of course, but I DO like wearing blazers and pencil skirts, so I guess it’s kind of tragic that I just don’t have a lifestyle that requires this kind of look, really.

Finally…

pencil skirt and cardigan

Hell Bunny cardigan; Boden shoes

10. With a cardigan

Because if you can’t wear it with a Hell Bunny cardigan, I just don’t want to wear it. The end.

Er, no, that’s literally the end. I mean, I could probably have gone on for the rest of the day, putting together various pencil skirt outfits, but they’d just have been even more variations of the ones above, and I think you get the idea, don’t you?

10 pencil skirt outfits to try

10 pencil skirt outfits to try
14 Comments
  1. I love all of these!! I really love the ‘daydreamer’ top but they don’t do a small enough size otherwise I deffo would have bought it! You look FAB in the blazer and heels combo 🙂 I love these style posts that you do – you’ve inspired me to maybe start doing them myself xo

    Char | http://www.charslittleblog.blogspot.co.uk

  2. Hilarious post – yee haw to you too! I seriously had never considered the plaid shirt/pencil skirt/cowboy boots combo. About to consider it now though! Thanks for the inspiration.

  3. I definitely want to wear a pencil skirt with cowboy boots now… I forget what I was even going to write now before I saw that comment, that’s how bad I want to do it. Actually, I had been thinking about exactly this, just this morning. I had been temporarily distracted by doing my job, but now back to the important things – cowboy boots with a pencil skirt.

  4. Love this post, I always struggle with how to wear a pencil skirt as I feel over dressed in one. I have one hanging in my cupboard which I can’t bear to part with but have never warn

  5. I would have never thought about pairing it with a baggy jumper or a plaid shirt, but think they look fab. I’ve gotta try that – My work is pretty casual but I do like to make an effort and that strikes the right balance between both!

  6. I love this post! I’ve been beefing up my resume because I need to begin looking for office-y jobs soon (ugh), and I’ve been wracking my head as to how to make office clothes interesting, and this was extremely helpful (pity the strapless top would need a cardigan to make it work appropriate!)

    I’ve actually been looking on the site (and probably not very well) for an office-like capsule wardrobe and I haven’t been able to find one, though the other posts you made have given me some great ideas. If you’re ever stuck for posts to make once you’re back from your vacation, I’d love to see a post on that! And if you’ve already done one and I’ve just failed to find it..well, that’s embarrassing 🙂

    1. Because it’s been such a long time since I worked in an office, I don’t actually have many clothes that would work for that, unfortunately – I’m probably quite out of touch with office dress codes by now, too!

      1. Oh wow – thank you for replying, especially while you were still on vacation – I appreciate it very much!
        I don’t blame you for not owning any office clothes – they look so boring to me. It’s a far cry better than a barista uniform any day (at least I can wear different pairs of beautiful shoes to the office), but they’re not the most exciting.
        Thank you again for replying. I hope you’re settling in alright after your vacation!

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