The Hunt: Black Pencil Skirts

Moschino Cheap & Chic Bouclé Wool Pencil Skirt

2016 Update: Check out our latest discussion on stylish pencil skirts for work

Sure, we all know what basics professional women are supposed to have in their closets, but if you’re buying one for the first time or replacing one you’ve worn into the ground, it can be a pain to find exactly the right incarnation in stores. In “The Hunt,” we search the stores for a basic item that every woman should have.

I have had two favorite black pencil skirts in my closet for years.  The first: a thick black wool one from Ann Taylor — perfect for winter months with tights (although I’m sure I’ve worn it bare-legged as well, whether advisable or not).  The second: a lighter weight Celine skirt, inherited from a friend when she left Wall Street for a more casual lifestyle in California.  Readers, which are your favorite pencil skirts? Are there any that you buy year after year in different colors and fabrics?

Anne Klein Skirt, PencilI’ve said it before, I’ll say it again: for affordable suit separates I really like the “every day value” lines at Macy’s, with pieces such as this Anne Klein Pencil Skirt.  It’s available in sizes 0-16, it’s lined, and it has a matching jacket and pant.  The skirt is $59.98. Anne Klein Skirt, Pencil
 Halogen® Seamed Pencil SkirtA few months ago, Nordstrom changed the design of the Halogen skirt, angering many readers who had considered the prior incarnation to be the perfect pencil skirt. While change can be maddening, I still hear many readers singing the praises of this one, and it’s still highly reviewed on the Nordstrom website. It’s currently available in more than a dozen colors, regular and petites, for $34-$69. Halogen® Seamed Pencil Skirt
No. 2 pencil skirt in double-serge woolJ.Crew’s No. 2 pencil skirt in double-serge wool is another classic. Right now it’s available in 3 basic colors (black, tan, gray) for $130, and a variety of fun colors for $98. (Oh, and it’s available in regular, petites, and talls, sizes 00-16.) No. 2 pencil skirt in double-serge wool
Wool Pencil SkirtI think this woo/Lycra blend looks like the perfect pencil skirt.  I like that it’s fully lined and has an invisible zipper.  It’s $148 at Brooks Brothers (sizes 0-16). Wool Pencil Skirt
BOSS Black 'Veronice' Tropical Wool SkirtThis well-reviewed skirt from BOSS Black is a tropical-weight wool, with a bit of stretch for added comfort. I like the slightly wider waistband. It’s available in sizes 2-14, for $250. BOSS Black ‘Veronice’ Tropical Wool Skirt
Moschino Cheap & Chic Bouclé Wool Pencil SkirtBouclé can be tricky in jackets (it never seems to lay right, it always seems to add weight, etc) but it works surprisingly well for pencil skirts. I love the bit of nubby texture, as well as what looks like a nice fitted shape. It’s $395 at Nordstrom. Moschino Cheap & Chic Bouclé Wool Pencil Skirt

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  1. I have been entirely happy with my Jones New York pencil skirts.

    • Oh! Another Susan.

      Well, this Susan has never bough anything from Jones New York, but will consider it. ;-)

      • heehee. There was another eek poster last week. I’m considering changing my moniker to T-Rex so I can really go claw to claw with Godzilla.

  2. Pendleton. I swear to dog.

  3. Woods-comma-Elle :

    I really like the cut and fit of the Ann Taylor tropical wool skirts, but they get so creased!!!

  4. CPA to be :

    I have several seasons worth of wool BR pencil skirts. The first couple I bought were both black, then I got a charcoal one, a taupe one, and a navy one. The black and charcoal material is noticeably thicker and wrinkles a lot less than the navy and taupe, although they are all wool spandex blends. I’ll keep buying skirts there, since it’s one of the few options I have in my area, and they fit me well, but just wanted to give a heads up about the difference in material quality. I’m not sure if this is a seasonal thing? Sell lighter weight “seasonless” wool in summer? Or is the material is going to be this cheap going forward? I haven’t had time to check our their seasonless wool this fall yet.

    I should also add that the newer BR pencil skirts are actually longer than the older ones I have by at least an inch, and I think they may be a little bit more roomy as well.

    • CPA to be :

      Oh, and despite the flimsier material in the new BR skirts, they have improved them somewhat by lining the waistband. Nothing irritates me like an unlined waistband.

  5. An enthusiastic vote for the J. Crew no. 2 pencil skirt! It seems to flatter just about every different shape. I also confess to falling slightly for their vanity sizing. No, J. Crew, I’m not even close to a size 0, but thanks for making me feel like I am by making your skirts huuuuge.

    • a passion for fashion :

      I have also become a lover of the no. 2 pencil skirt. i recently bought 4 — 2 wool and 2 cotton — all on sale. they make me feel wonderful when i wear them and i know they go with so many things for an easy, polished look: a jackie sweater set and a strad of pearls, a crisp white buttondown, a silk shell and a belted flowey cardigan, a ruffled shell or t-shirt and a blazer, and the list goes on . . . . its like a modified uniform for me.

    • Big fan of the No.2. I also bought the black Telegraph (?) skirt last year and the length is wonderful (I’m 5’10 and it hits at the knee!).

    • yesss forgot about j.crew. one of every color for me!

  6. Tights Question :

    I have a very basic question. How do you wear skirts/dresses with tights?

    I am in medium law and am personally uncomfortable wearing knee high boots to the office – I have a very hourglass figure and feel that boots with a skirt come across a bit too sexy on me, although look perfectly appropriate on other people at my office. But, when I wear tights with pumps, I feel like I am either in elementary school again or my legs look like tree trunks. Plus, the opaque tights against pumps just seems off to me.

    Any advice? Tights style suggestions? Or things to avoid?

    • TO lawyer :

      What colour are your pumps/skirt/tights? I know Belle from CapHillStyle gets a bad name for being judgey here (and she is I think, although I don’t mind it) had a good rule of thumb: out of the 3, at least 2 should be the same colour. I’ve found this helps with my legs looking stumpy. That said, not all of my pencil skirts look good with tights… the ones that don’t, I generally wear with black panyhose and I like the look much better.

    • For most of the year, I can’t even imagine wearing skirts without tights. I would just be too dang cold without them.

      So let me introduce you to the wide world of tights. The styling suggestions are boundless! If you are uncomfortable with opaque tights at the moment, you could start by trying semi-opaque or patterned. If you are wondering whether a pair of tights is going to be opaque, check out the denier number – the lower the number, the more sheer they will be (e.g. 20 denier tights are practically nothing, but 200 denier would be super opaque and warm).

      If you want to try wearing boots with your skirts, why not venture into the world of patterns? Having a bit of pattern peep out between boot and skirt can be quite fun, especially if a whole legfull of pattern would be too much.

      If you want to try wearing tights with pumps, don’t worry, you are probably just being overly critical of yourself (we are all guilty of that). If you like the look on someone else, just try it. It might simply be a question of getting used to the way it looks. If you are concerned about looking like you are in elementary school, stick with a solid black or brown, and stay far away from elaborate cables etc., which are what most people would associate with the schoolgirl look. Solid black tights are always a safe bet and my winter staple.

      I think the main thing is to just not take it too seriously. Have fun with it! :-)

    • Diana Barry :

      Riding boots instead? I think that heeled boots (esp stiletto heeled boots) come across “too sexy” with pencil skirts, but riding boots don’t. YMMV if your office is too dressy for those.

    • I match the tights to my shoes, as much as possible. Just like wearing nude shoes with bare legs, it elongates your legs.

    • I find dark grey tights to be a lot more wearable than black tights, if that helps. Of course, that cuts down on your options for wearing matching shoes, which, to agree with Bluejay, really does elongate nicely. I disagree, however, with Cap Hill’s 2/3 rule – if your work environment is casual enough to wear a colored skirt, then I think that gray tights and black shoes work just fine. I also really like gray tights with red shoes, though that’s a bolder look (fine for my workplace, might be pushing it in others).

    • hellskitchen :

      Try to find tights with subtle patterns – self tonal vertical lines or semi-sheer chevron. They will help with that feeling that your legs looks like stumps (I know exactly what you mean). Wear a bit of a heel, even if it is just 1 or 2 inches. And darker the tights, the better it is. I have a pair of grey tights that reflect a lot of light and therefore look more stumpy than my darker ones.

  7. 2/3 attorney :

    What’s with the shoes on the model for the Moschino from Nordstrom? It looks like she has hooves!

    • Brooklyn, Esq. :

      Haha, so glad someone else noticed…at first I thought Kat might have picked that photo to provoke us into commenting. :)

  8. Michael Kors Ponte Pencil skirt
    I have serious waist gap issues with trousers and this skirt fit me off the rack.

  9. Why no plus sized picks, Kat? In a round up of this size, I’d expect at least one token plus.

    • The Anne Klein skirt comes in plus, but isn’t in stock right now. Do you have any recommendations for plus size black pencil skirts? I’m sure others would find them helpful, as well.

    • I am not even plus size and I thought the same thing. Especially a black one becauseI feel that black pencils are very flattering on most plus size ladies.

    • attiredattorney :

      Talbots makes a triacetate pencil skirt that is fantastic. It never wrinkles and is available in petites, plus and regular sizes. The plus sizes come with a little hidden elastic in the waist that really helps improve the fit.

    • AnotherLadyLawyer :

      I can’t figure out the comment-lining-up, so hopefully this goes in the right place. I live in Jones New York black pencil skirts (more often than not from the JNY outlet). I also love the Talbots pencil skirt mentioned above/below.

  10. Still relevant so reposting because I’m jealous: lucky sizes (14,16) the Long No. 2 in safari cat is on sale for $49.99.

  11. Anyone have any good pencil skirts that have a bit of stretch in the waist but are made for narrow-waisted women?

  12. A Ninny Mouse :

    Any recommendations for the larger assed among us?

  13. Since this is an A line skirt, I realize it’s not a pencil but I got this recently from Kohl’s website and like it so far:

  14. I’m still a fan of “The Skirt” from Nordstrom, but also really like J Crew’s No. 2.

  15. Any suggestions that aren’t wool, for the vegan professional ladies out there?

  16. Any recommendations for pencil skirts for those of us that are boxy? So many skirts nip in at the waist- and my waist (after having 2 kids especially) is nonexistent.

    • The J. Crew No. 2 has no waist. I am not especially curvy but I still have to have the waists on these taken in, so they’d probably be good for you.

    • Seconding the J.Crew No. 2 pencil skirt. My waist is about 2 sizes larger than my hips and I can wear a size 0 or 2P in this skirt. I don’t find it particularly comfortable unless I tuck a layer in, but the waistband is definitely cut large enough. I think the size 0/2P has around a 28″ waist (just go up a size from regular if you need to order petites).

  17. Just want to add my voice to the discussion of The Skirt. I happen to like the new version better. Size 10, hour glass, for what it is worth. I don’t want those who are curvy to write off the new version. It totally works.

    • Really? You are the first hourglass reviewer that I’ve seen who actually likes it. I don’t have a Nordie’s near me (yet) so this gives me renewed hope for my next trip to one. I thought my days of buying The Skirt were over forever.

  18. Target, if you have an hourglass or pear-shaped figure. I’m not kidding. So many pencil skirts are cut straight rather than tapered (sheath style), but not Target’s. They have a high, wide waistband and are sewn extra-curvy in the seat. They look funny on the hanger but look fabulous on.

  19. I love Lofts pencil skirts. Come in a million colors per season. I have a baby pink one, hot pink one, as well as the basic khaki, grey, black. Banana Republic has nice tweed wintery options but they tend to fit me funny (size 3/4, 5 feet tall, absolutely no legs).

  20. research lawyer in SV :

    Another non-pencil version- I just bought this Ellen Tracy black flared skirt on sale. The fabric is very lightweight and easy to wear on warmer days.

  21. Hope from Sydney :

    May I just hijack? I am so excited, have just booked to bring my 2 daughters 14 and 19 to New York from Sydney for Christmas and New Year.It will be their first trip to New York. I have all of the accommodation arranged and have booked the Rockettes. Apart from shopping, the Xmas lights,tree,ice skating , usual touristy things etc, can native New Yorkers please suggest some experiences which will be unforgettable for them. Also I’m wondering what might be a great place to eat on Christmas Day , as our family tradition is a lunch. Can’t wait!

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