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Un-Fancy

Outfits: Spring, spring outfits

4 ways to style a black pencil skirt

03/24/16

how-to-wear-a-pencil-skirt-153-3

I surprised myself last year and added a black pencil skirt to my wardrobe.

I work from home and lead a seriously casual lifestyle, so a black pencil skirt never seemed like a good fit for my wardrobe. But then I found this stretchy, pull-on, Ponte version of a pencil skirt and I was all kinds of smitten.

I’ve never really been a skirt / dress girl — I’m more of a jeans / shorts girl.

But this simple skirt taught me that the right skirts and dresses can be off the charts comfortable.

And I’ve noticed that the workhorses in my closet are the pieces that look fancy but feel comfortable.

So, black pencil skirt, I’m super happy to see you again this spring.

Here are 4 ways to style it with a casual + Unfancy vibe:

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LOOK ONE: Stick with a palette of black, b&w stripes, and denim. Pair a boxy crop top with your pencil skirt and finish with a slightly oversized denim jacket. Slip on sandals with a low heel, grab your tiniest cross body purse and you’re obviously on your way to wherever the cool kids are hanging out.

01 | Crop top(old) / similar (made in USA) / similar in solids colors (made ethically)

02 | Denim jacket (old) / similar (made in USA) / similar for less

03 | Bag by Marc Jacobs

04 | Sunnies by Ray Ban

05 | Sandals by Madewell

06 | Skirt by Madewell (old) / similar on sale (fit note: runs small, size up) / similar (made ethically)

how-to-wear-a-pencil-skirt-154

LOOK TWO: Easiest outfit recipe ever: white tee, black skirt, and denim jacket. But with all these basic pieces, make sure to add a subtle statement with an accessory. To me, the key to this outfit’s success is that necklace. It’s minimal, but it adds another dimension to the outfit — just a hint of pattern.

01 | White tee (old) / similar (made ethically)

02 | Denim jacket (old) / similar (made in USA) / similar for less

03 | Necklace c/o Natalie Borton (handmade in the USA)

04 | Sandals (old) / similar (made ethically with an emphasis on empowering women + communities)

05 | Bag by ONA

06 | Sunnies by Ray Ban

07 | Skirt by Madewell (old) / similar on sale (fit note: runs small, size up) / similar (made ethically)

how-to-wear-a-pencil-skirt-155

LOOK THREE: Feeling edgy? Here you go: Stick with an all-black palette. Tuck the tank into your skirt, add booties, and grab your moto jacket. Break it up with a cheetah patterned clutch. Oh, and don’t forget your fresh fruit. Hah! The things we put in these flat-lay photos. Calling myself out + not caring one bit. :)

01 | Tank (old) / similar (made in USA) / similar with lace-up detail (made in USA)

02 | Moto jacket (old) / similar

03 | Ankle booties c/o Fortress of Inca (made responsibly + sustainably) 

04 | Sunnies by Ray Ban

05 | Cheetah clutch (old) / similar (made in the USA)

06 | Skirt by Madewell (old) / similar on sale (fit note: runs small, size up) / similar (made ethically)

how-to-wear-a-pencil-skirt-151

LOOK FOUR: Two shades of blue mixed with that warm caramel — bless my happy heart, it’s my favorite color combo! If you’ve been looking for a way to shake up your chambray shirt, try tying it around your waist and pairing it with a darker chambray or blue top. And there you go. You’ve got a cute outfit — great for running errands or a quick coffee date.

01 | Sleeveless chambray shirt (old) / similar with crop fit / similar in light wash

02 | Chambray shirt by Madewell 

03 | Skirt by Madewell (old) / similar on sale (fit note: runs small, size up) / similar (made ethically)

04 | Bag by ONA

05 | Sunnies by Ray Ban

06 | Sandals (old) / similar (made ethically with an emphasis on empowering women + communities)

So what about you? Do you have a black pencil skirt in your closet? Do you ever dress it down?

xo

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53 Comments

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Comments

  1. Maia says

    March 24, 2016 at 5:40 pm

    I do own a black pencil skirt but never wear it, so thank you for giving me some ideas! I think the all black look is my fave. Might have to try and rock that tonight after work.

    Reply
  2. Janet Sodders says

    March 24, 2016 at 6:00 pm

    I love your posts! All of these outfits are adorable. Thanks for the ideas.

    Reply
  3. AnnMarie says

    March 24, 2016 at 6:23 pm

    I just picked up a fun grey sweater-ish pencil skirt from H&M (wearing it today, actually!), so this post comes at just the right time! I don’t really have any jackets, though, just lots and lots of cardigans, but I do like the jean jacket look…and I always wanted one as a kid. Also, I need to track down some comfortable, cute sandals for summer — yours look amazing!

    Reply
  4. Magenta deluxe says

    March 24, 2016 at 6:23 pm

    I have just purchased those beautiful Madewell sandals because I saw them on your site. I hope you get the credit for that.

    Reply
  5. Stacy says

    March 24, 2016 at 6:36 pm

    I have a casual-ish black pencil skirt (this one from Bridge & Burn: http://www.bridgeandburn.com/products/edith-black-skirt-f15?variant=8351936197) that I dress up for work, but I love seeing these casual options! Perfect fire-starters for wearing that black skirt outside of the office!

    Reply
  6. KaTie says

    March 24, 2016 at 6:57 pm

    Love! Your style is so on fleek girl! Thanks for the inspo.

    Reply
  7. Stephanie says

    March 24, 2016 at 8:15 pm

    Love love love!!!

    Reply
  8. Lisa says

    March 24, 2016 at 10:29 pm

    loving all the outfits :)

    glad to see you’re posting again~

    Reply
  9. Cindy says

    March 25, 2016 at 12:42 am

    Love it! I guess I’ll spend this weekend looking for a pencil skirt. Definitely inspired. Will you be posting your entire spring capsule wardrobe anytime soon?

    Reply
  10. Mélodie says

    March 25, 2016 at 5:08 am

    okay so i could legit wear any of these outfits every day for the rest of my life! You truly have a great style!! I think i’m gonna have to consider a black pencil skirt for this spring now… you got me there! ;)
    xoxo

    Reply
  11. Lisa says

    March 25, 2016 at 6:02 am

    I have a similar black ponte skirt from Everlane that I love. I once front-tucked a drapey black tank in for the look of a casual dress. Will try your styling ideas, too!

    Reply
  12. Erica quint says

    March 25, 2016 at 6:24 am

    You’re such an inspiration to me. I love all of your outfit ideas.

    Reply
  13. Tanya Woodard says

    March 25, 2016 at 6:57 am

    Seriously LOVE your blog and really enjoy your playlists on Spotify. I teach at a fitness studio in South Dakota, and I admit I use your music as inspiration for many of my workouts. So, THANKS! Just out of curiosity, do you have tips from studio to street wear? I love my workout gear, but its not something I want to wear making errands.

    Reply
  14. Heather says

    March 25, 2016 at 7:14 am

    I’ve owned a black pencil skirt for over a year that I have worn maybe two times and was thinking of getting rid of it but now with these great ideas, I’m thinking it may need to be worn more often! The best part is I have most of the things you have paired with the skirt — bonus! I am so in love with un-fancy…thanks for all the inspiration!

    Reply
  15. Sarah Esh says

    March 25, 2016 at 7:24 am

    I have a Ponte pencil skirt in my wardrobe and that thing is a workhorse. I, too, am a casual girl, but once in a while, for weddings and funerals and church or a fancy date night I need something a bit more – and that is when I pull that skirt out. In the winter I’ll wear black tights and booties with it, in the summer its Birkenstock’s or heeled sandals of some sort, and as for the other seasons, flats all the way.

    Seeing this outfit combinations makes me think, even more, that I do need to add a denim jacket to my capsule.

    Reply
  16. TaÍs Luz says

    March 25, 2016 at 7:28 am

    I’m so happy to see you back!!! ?
    When I found your blog you was out, I looked all your older posts and waiting for your new ideias!!!
    Thank you, you made my wardrobe more easy!!!

    Reply
  17. Dawn says

    March 25, 2016 at 7:33 am

    After seven years wearing at least every other week my black pencil skirt finally bit the dust last week. It’s so hard for me to part with old favorites when they finally wear out. I loved wearing it to work with a black and white striped long sleeve tee. The skirt was dressy enough to make it totally work appropriate.

    Reply
  18. Lily says

    March 25, 2016 at 8:22 am

    Thank you for sharing these great ideas! I really appreciate your style- it’s such a nice balance of modesty without being frumpy, and hip but not too trendy. Your casual sensibility is so wearable and relatable, too!
    My pencil skirt is black and white stripes. When I first got it I was self-conscious because it was out of my comfort zone, (I’m a jeans and shorts girl, too!) but with the right top and shoes I made it my own. It’s fun to surprise yourself, isn’t it?

    Reply
  19. Marie @ The Business of Blooming says

    March 25, 2016 at 8:55 am

    I feel the same way about skirts..that somehow they can’t be comfortable, but I can see myself wearing every outfit here, especially the last one. Love it. So maybe I’ll give them a second try.

    http://www.thebusinessofblooming.com

    Reply
  20. Erika says

    March 25, 2016 at 9:05 am

    Love that you include items of sustainability and ethically made garments. Thank you!

    Reply
  21. Mimmi says

    March 25, 2016 at 9:58 am

    I have a pretty dressy pencil skirt and I love pairing it with a t-shirt and sneakers. Sometime I had a statement necklace for a twist. I feel great wearing that and will definitely take inspiration from your suggestions :-)
    Also, I’m glad to have you blogging again. Hopefully you will write something on beauty/make-up again soon.

    Reply
  22. kimithy says

    March 25, 2016 at 10:45 am

    I do a similar thing with a dark blue stretchy pencil skirt – I think the little hint of color makes it more casual, and it’s one of the only things in my wardrobe that isn’t gray, beige, black or white, so it kind of punches up any outfit!

    Reply
  23. Kamden says

    March 25, 2016 at 10:50 am

    Thank you for posting! This is my favorite blog ever. I am so grateful for the freedom you give for us to use the items we already have with a few updated, stylish twists. Thank you for being real and laughing at some of the funny, unrealistic things that go with a style blog or beautiful photography and for keeping your priorities straight.

    Reply
  24. kimithy says

    March 25, 2016 at 10:53 am

    PS: I don’t wear skirts often due to inevitable discomfort due to my thighs rubbing together (same reason I hate shorts, as I get annoying shorts-ride-up), but got a tip recently from a guy who had chafing issues when he would wear swim trunks w/built-in briefs – wearing bicycle shorts underneath! They’re usually tight enough to stay put and not add much bulk, but help a lot with the ouchies from thighs rubbing together, especially if you’re active (which I am, so can be particularly miserable in our hot Austin summers).

    Reply
  25. Mary says

    March 25, 2016 at 12:10 pm

    Caroline, I just wanted to say that your blog is (and always has been) so refreshing! It’s at once a reminder that I don’t have to strive for things I don’t have to make me happy, and an inspiration that I can make life and outfits beautiful with less. Thanks for all of that :)

    Also, thanks so much for talking about slow fashion and including ethically sourced items in your links! I’ve been learning more about that recently, and it’s making me so thirsty to spread the word and really get serious about what I purchase.

    Anyway, you’re the best! Thanks again for all you’re doing here!

    Reply
  26. Elizabeth says

    March 25, 2016 at 12:36 pm

    Hi Caroline! I’m so happy that I discovered your blog. I love all of these outfit ideas and am looking to put a black skirt into my rotation because of this post. I am also getting so inspired by your older posts to try a capsule wardrobe. A question for Caroline or any of the other ladies here who might read this…my work life and non-work life are pretty different, being a scientist/science educator by day and then splitting half of my non-work time between NYC and a super-rural setting. Does it completely go against the spirit of the capsule wardrobe to have a “work capsule” and a “home/non-work capsule”? Has anyone tried this? I feel like I want to give this capsule experiment a honest try, and that having more than 37 items due to having two capsules might mean I’m not being as creative as I could be. Anyone have thoughts on this? Thanks!

    Reply
    • Hannah says

      March 26, 2016 at 1:03 pm

      I also have super distinct work/home wardrobes – at work I have to wear a conservative suit everyday, but at home I like to look like an early 80s surf bum. I used to try to buy pieces that I could wear both at work and at home but after years of not being totally happy with what I had on in either location I just said screw it and now I have two totally different sets of clothes – in my last apartment I even kept them in separate closets, which was great. I don’t do a strict capsule wardrobe really, but I don’t think having two groups of 37 or whatever you go with defeats the purpose at all – it’s supposed to be about simplifying your life and decision making processes right? And if having distinct sets of clothes does that for you, then I say go for it!

      Reply
      • Laura says

        April 4, 2016 at 2:06 pm

        Hi Hannah,
        I am a little late to reply on this, but I have a capsule of 36 pieces… Including work wear!! I know crazy right! I am a teacher. I have 8 pieces that are specifically for work so pants, blouses & blazer. It works very well I have a top for each day of the week! Then the rest of my items are for weekends/evenings/occasions. Believe or not this works great as everything gets a lot of wear, and when it’s time I just replace some things :) hope this helps!

        Reply
    • TRina gupta says

      March 26, 2016 at 10:27 pm

      Hi Hannah, I was about to post a comment on this lovely blog but saw your note and had to throw in my two cents! I have a similar situation to yours and find that having multi-tasking pieces in my wardrobe is all it takes to transition back and forth between urban/city life and suburban/rural. Caroline’s pencil skirt is a prime example and I’m posting my blog post on styling a black pencil skirt 3 ways below as well. Mine are all work looks but you can see from Caroline’s flat lays how the same item can be styled for both work and casual settings! Hope that’s helpful:)
      Trina from: http://www.petitestylestudio.com

      Reply
  27. Rebecca says

    March 25, 2016 at 1:14 pm

    oh man THANKYOU for this! I have a stretchy pencil skirt that I only ever dress up. I never even thought of making it casual!

    Reply
  28. Holly fish says

    March 25, 2016 at 1:52 pm

    This is so odd!! I sat down to read this post while waiting for my husband to get ready for our Good Friday service. And I am wearing a black pencil skirt with a button up denim tank. Crazy! I did add a black cardi, though, since it is Good Friday and I wanted to wear mostly black. Thanks for the inspiration to wear my pencil skirt in cheerier settings! ✝

    Reply
  29. Lauren says

    March 25, 2016 at 2:33 pm

    Thank you so much Caroline! I always relate a black pencil skirt to dressing up. I’m so excited to try these three new ways! :)

    Reply
  30. KATE says

    March 25, 2016 at 3:00 pm

    I don’t have a pencil skirt and had never considered owning one, until now! I wear a lot of flowy skirts in the summer but I like this idea, I can’t say no to comfortable knits, and it would minimize any worries about the wind exposing my under-things.

    Reply
  31. Karin Rambo says

    March 25, 2016 at 3:02 pm

    Very cute! I love all the different looks! I also added a black pencil skirt this capsule that I thrifted and I really love it. I can’t wait for it to be warm enough for me to style it!

    Karin Rambo | truncationblog.com

    Reply
  32. Sheri says

    March 25, 2016 at 3:41 pm

    Thank you for so many great, casual ideas for my skirt. I usually reserve it for work or nights out. I will definitely get much more wear out of it now.

    Reply
  33. Kelly nh says

    March 25, 2016 at 5:23 pm

    Love me a basic in the closet, but even more so I adore the cheeky pear shot in this post ?

    Reply
  34. Astrid says

    March 26, 2016 at 7:41 am

    Lovely ideas for a basic pencil skirt! I only have a quite formal one, but now want a more casual, stretch-type one! Love the denim jacket too and, funnily enough, I have never considered mixing tan with a black skirt but this works so well! Thank you! :-)

    Reply
  35. Emma says

    March 26, 2016 at 1:01 pm

    Im all about the secret pyjamas.. Comfy but looks nice. This post is great as i just made a ponte skirt almost identical – good inspiation to wear it now :)

    Reply
  36. lifeeofgirls says

    March 26, 2016 at 6:07 pm

    Very great looks, I love them :)

    Reply
  37. TRina gupta says

    March 26, 2016 at 10:32 pm

    I love these super easy styling ideas with an item almost everyone has in their closet. Thought I’d share 3 work looks with my black pencil skirt to hopefully spawn some more outfit inspo: http://bit.ly/1oM9tLU
    As always, love your posts Caroline❤️

    Reply
  38. welovefur says

    March 27, 2016 at 9:23 am

    I love the second look. So simple so chic
    You have a interesting blog.
    Visit mine if you want
    http://www.welovefur.com

    Reply
  39. Georgie says

    March 27, 2016 at 5:03 pm

    Yes! Thank you so much! I have a stretchy knee length black pencil skirt – bought it straight out of university a few years ago as I thought I needed an ‘office’ look but really struggle to know what to wear with it without looking frumpy, especially as I can actually dress much more casually than I imagined. I never even thought about wearing it for weekends though! This is perfect. x

    Reply
  40. kate c. says

    March 27, 2016 at 5:36 pm

    thank you SO much for emphasizing ethical clothing choices! it is something that’s super important to me, and it’s so exciting to find a fashion blog that is talking about it! i’ve loved finding new options through your suggestions, thank you for doing all of the research. keep it up girl! <3

    Reply
  41. Mun says

    March 27, 2016 at 11:36 pm

    Thanks for reminding me that I have a black skirt lying somewhere that needs to be loved!

    Reply
  42. Robin says

    March 28, 2016 at 9:49 am

    I love your blog, thanks for all of the great outfit ideas! I did have a question – I am thinking about digitizing my closet to help organize my outfits. There are a few apps out there but I’m not sure which one is better. Do you do this and which app do you use? Thanks so much!

    Reply
  43. Marine says

    March 29, 2016 at 8:50 am

    I also have a very casual lifestyle, but I’m attracted to “professional” pieces. That’s one of the reasons I started following you way back when – because you find a way to make fancy look casual! I do it slightly differently – I’m a huge fan of fun patterns and prints on basic pieces. For example, I have a black pencil skirt, but it has little white giraffes embroidered all over it! I also have a white button down that is covered in zebras. Fancy, but fun!

    Reply
  44. Laura r says

    March 29, 2016 at 5:04 pm

    Love love love

    Reply
  45. Laura r says

    March 29, 2016 at 5:04 pm

    Love

    Reply
  46. Joepet Macariola says

    March 29, 2016 at 9:45 pm

    I’m loving your style!!! Thanks for sharing this!!!

    Reply
  47. Mary says

    March 31, 2016 at 6:20 am

    I wear one to work but would happily wear a black pencil skirt + striped t on Friday (for a not quite but almost casual Friday look).

    Reply
  48. Susana says

    March 31, 2016 at 9:54 am

    Hi Caroline! When we’ll be seeing you capsule wardrobe for spring? I started this season and can’t wait to see your picks. Love the blog!

    Reply
  49. Kara | Daily Opulence says

    April 9, 2016 at 8:30 pm

    Loving looks 3 & 4. I have always just tucked my shirt in with a pencil skirt. These looks are very refreshing!

    Shop & Get Inspired | http://www.dailyopulence.com

    Reply
  50. Akanksha Padhi says

    April 15, 2016 at 10:59 pm

    Love the way you have teamed up different pieces.

    x https://ahsknaka.wordpress.com/

    Reply

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