Sure, we all know what wardrobe essentials for work 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.
We haven’t done a hunt for pencil skirts in too long — what are your favorite pencil skirts for work these days, ladies? (Are you Team A-Line, Team Pencil, Team Dress, or Team Pants?) I’ve always been a fan of pencil skirts as a great structured basic — pair it with a low heel or sleek flat, pretty much any kind of top (blouse, fancy tee, pullover, cardigan) and a necklace or two and you’re good to go. If bare legs are OK at your office (know your office) then Jockey slipshorts or Spanx are great to wear beneath them — meanwhile check out our favorite tights for work as the weather gets colder. (We also have a Guide to Pantyhose, should you need them for interviews, very formal/big days, or if you just prefer pantyhose!) An important note on pencil skirts: don’t forget to cut the vents! Many pencil skirts come with a slit in the back, side, or front; this may be sewn shut with a loose little criss-crossed stitch.
These are some of the pencil skirts for work that we’re loving now — we’d love to hear your favorites!
Curious for older roundups of great pencil skirts for work? Here they are from 2016 and 2012.
 Old Navy’s ponte collection is full of great basics. They may not be as thick as the ponte you’ll find elsewhere — and they may not last as long as more expensive versions — but as far as style, structure, and price point, they’re a great basic if you’re building a work wardrobe with no money. The pictured skirt comes in 5 colors, sizes XXS-XXL, and today is marked to $20. Ponte-Knit Pencil Skirt for Women |
 This scuba skirt has been around for years, and it’s always a top seller at Macy’s, coming back again and again in fun colors and prints. While it’s $59 full price, it’s often marked below $40 — before you even get to coupons and so forth. It comes in regular, petite and plus sizes, and is machine washable. Alfani Scuba Skirt |
 J.Crew’s No. 2 pencil skirt is a classic — but let’s talk for a second about the best-selling pencil skirt in double-serge cotton at J.Crew Factory, where a lot of more traditional J.Crew basics seems to live. They’re regularly priced $69 (today on sale for $35 in 7 colors), come in petite and regular sizes 00-20, and in general are a great basic. Word on the street is that J.Crew is going to get a “refresh” in September, so we’ll see what becomes of the No. 2 pencil skirt — right now there are very limited sizes and colors left. Pencil skirt in double-serge cotton |
 This ponte knit skirt from Vince Camuto has been a best-seller at Nordstrom and Zappos for years; like the Alfani skirt it’s a pull-on style. We’re picturing it in plus sizes, but it also comes in regular sizes; both are on sale as part of the 2018 Nordstrom Anniversary Sale. Vince Camuto Ponte Knit Skirt |
 The Martha Skirt at Boden is always a great option if you’re looking for a fun print — it comes in petite, regular and long sizes 2-18. It’s regularly $110, but right now it’s marked to $55-$66 depending on color. (Nordstrom also has one print, full price at $110.) (Don’t forget to check out our recent roundup of how to build a work wardrobe at Boden!) Pictured: Martha Skirt |
 There are a lot of nice splurge options for pencil skirts, but in terms of “classics” I’d probably go for this one: the high-waisted pencil skirt from Black Halo. The below the knee length can be difficult to style with flats, but with heels it’s a no brainer — and the high waistline makes for a super sleek silhouette. It’s $230 at ShopBop, Amazon, and others. (Other options for a splurgey but classic pencil skirt: St. John and Armani.) Pictured: High Waisted Pencil Skirt |
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Ellen
I love these pencil skirts! If ONLY I had the tuchus to wear these! FOOEY!
Anonymous
I am pretty much obsessed with the below-the-knee look right now – I just think it looks so chic and fresh.
Anon
Do you wear sky-high heels with them? How do you prevent legs from looking stumpy?
Anonymous
I wear heels with them (and often ones with a slight platform for even extra height without losing walkability.)
Anonymous
Oh, pencil skirts. They make me look pregnant and my thighs are too big for them. Super fun.
Anonymous
Okay, so don’t wear them?
Jo March
I really wanted to love the Old Navy skirt, but the proportions just weren’t right for me. I have multiple pairs of the Pixie pants and have multiple ponte dresses from Old Navy that I wear to the office, but something about these skirts did not work for me. Just a word of caution to try them on in person before buying.
Anonymous
The Old Navy ones look terrible on me! They stick out super weirdly at the hips.
Robin Luich
New York and Company have the thick double lined clingy stretch waist that I love but none in black. Very pretty floral designs for church.I need a nice black one that goes with anything.
Shortie
Not in stock right now, but Loft usually has good basic pencil skirts. Decent weight, fits my fairly narrow hips. And the zipper is in the back, not the side, so easier to get tailored.
anon
On the opposite end of pencil skirts, I could use some vacation fashion advice. I’m doing a sightseeing tour of Chicago with my kids. The last time I went, I made the mistake of wearing fashion sneakers, instead of real sneakers, and dearly paid the price. (Seriously, this was a decade ago and I still remember how sore and miserable I was!) So, I’m pretty committed to wearing my comfortable, broken-in running shoes. And, um, they’re BRIGHT turquoise and neon red. What do I wear? Should I just fully commit to activewear, because at least the footwear blends in? Or is it possible to wear chino shorts or jean shorts without looking completely goofy?
CHL
As a native and current Chicagoan, no one will care. So you’re a tourist? Big deal – there are lots of tourists and I can guarantee someone will be wearing something less cool than you. And some of us natives will be commuting in our MMLF dresses with ratty Birks or gym shoes. Be comfortable! Enjoy Chicago!
Anonymous
MMLF dress + gym shoe commuting Chicagoan here! Wouldn’t be caught dead commuting in decent shoes
Torin
Others may disagree but I think denim shorts, tank top, and running shoes looks fine. It’s not a fashion statement but it’s not hideous. Chinos I probably wouldn’t do though.
Anonymous
I just got back from NYC and it seemed like every single tourist was in athleisure. Cute stuff, not sloppy. I was really jealous and wished I had brought some instead of my regular “nice” clothes. I was so hot and uncomfortable. And your sneakers will look better with cute yoga crops than chino shorts.
anon8
I think fashion sneakers have come a long way in 10 years. I love my Vans and they are very comfortable. I bought them in Spain and they were great on all the cobblestone streets.
mascot
+1. I’ve got some sleeker New Balance in a slate color that I wear in situations like these. Also, Birkenstocks are in right now and work great if they are broken in. I did 8 miles of urban sightseeing a few weeks ago in mine.
NB300
New Balance 300s are my go to for ‘They aren’t really trainers’ requirements.
aBr
Check out APL shoes, which are fantastic. As someone that insists on super cushioned shoes for running (I’m looking at you Brooks Glycerin), these shoes have enough super and come in every color under the sun.
Anonymous
Native Chicagoan here, I wear activewear all weekend and I feel like everyone else does too. Yoga pants and running shoes will not be out of place and you’ll be comfy to explore the city!
mary
Can you find a simple cotton sundress you like? I found one at Old Navy. I wear it A LOT.
Better than putting together an outfit and I felt good about what I was wearing…
I’ve resigned myself- shorts only look good on my tween daughters…
anon
Love pencil skirts on others, absolutely despise wearing them. I’ll admire from afar!
abby
Ivanka Trump’s brand is closing!
Anon
I just want to put this out there. You look good in pencil skirts. That full skirt that you think is hiding your wide hips or thunder thighs or whatever is not doing any of that. Trying to cover any perceived flaw with large clothing doesn’t work. Large clothing looks large!
If you feel a pencil skirt is too revealing, do you wear pants or jeans? Because those reveal more than a skirt, other than the lower legs.
If you like the look of a pencil skirt and are wondering how to wear it – put it on and wear it. You’ll get used to it in a day.
Anonymous
+1. I avoided them for 15 years, tried one on and loved it. It’s such a flattering look when you wear it confidently.
Aggie
Hemlines are critical in a pencil skirt. Too long and they look frumpy, too short and the proportions are off or you are close to a mini skirt. Several brands make different cuts of pencil skirts, they do not have to be stick straight.
Anonymous
Argh. I want to agree with you, because I hate how I look in flared skirts now that they aren’t ubiquitous, but I haven’t succeeded at this yet. My waist is short and small, my hips are several sizes larger, and I honestly think I look like a short, plain Kardashian in pants, jeans, or pencil skirts.
Delta Dawn
I’ve posted this before, but I have bought the exact J.Crew skirt that is pictured here, and it fell apart while I was wearing it. The hem just… fell out. It’s a big hem, a couple inches of fabric, that just hung awkwardly and continued to unravel over the span of about half an hour until the whole thing fell apart. I had to tape the skirt back together to get through the day. After a fight with customer service (who didn’t want to do anything about it), they finally sent me a replacement…. which also fell apart while I was wearing it. Never again, J.Crew.
Panda Bear
That stinks! I had hems unravel on three pairs of Jcrew pants (I really liked the fit, so stubbornly kept buying new pairs). After I finally wrote a cranky review about the fallen hems, they contacted me and refunded me for all three pairs. So now I’m ambivalent on them.
Anonymous
Pencil skirts interfere too much with my commanding stride. Pants or a-line for me.
Super Anon
I am a mid-level associate and a client has asked me to dinner to celebrate the conclusion of a litigation I worked on. The dinner will include 3 people from the client and me. I accepted the invitation of course. Later the client let me know there will be an after-dinner event (think tour of a museum) that I am invited to as well. I am 5-months pregnant and the after-dinner event is scheduled to go past midnight on a weeknight. Do you think it would be bad if I only went to the dinner? During my pregnancy I tend to get really tired and start to feel sick if I stay up very late so I normally do not stay out this late. At the same time, I definitely don’t want to offend the client.
Torin
Absolutely fine to beg off on the after-dinner drinks.
Houda
Not even pregnant and I would skip the after dinner plans. I am notoriously grumpy at night because that is when my introvert self needs to rinse out all the social interactions of the day so the longest I can last is dinner. You don’t have any explaining to do and they have no reason to be offended. Enjoy the dinner!
Linda from HR
I’m kinda digging my plaid pencil skirt with buttons up the side, got it at H&M! Not exactly designer, I know, but I think it looks cute on me, especially with a black blazer.
Today I finally found out what kinda raise I’m getting. Not a super high number for base pay, but I’m getting a decent bonus, with talk of more bonuses throughout the year. Not that I needed a boost today, but I feel pretty great right now :)
Shauna
Banana Repiblic has one made of the same stuff as Sloan pants that I love – so much so that I have it in three colors
Sophia
Oohh! The Sloan pant is by favorite (and only) pant I wear. Do you know what the skirt is called?
Is it this one? https://bananarepublic.gap.com/browse/product.do?vid=1&pid=887869012&searchText=pencil+skirt
If it is, it looks like it’s super limited right now, but hopefully they’ll get more stock come fall!
Gemma
I’m a fan of Philosophy pencil skirts. Comfortable and flattering and they machine wash well. https://www.nordstromrack.com/shop/product/1572330/philosophy-apparel-solid-ponte-pencil-skirt?color=PEARL
Anonymous
I feel like pencil skirts need heels. When worn with flats, it looks a bit too much like a flight attendant uniform.
Anonymous
Lol what? No this is a you thing not a pencil skirt thing.
Anonymous
These are the comments that both make me feel clueless (What? Flight attendant uniform isn’t the goal here?) and also relieved that I read this blog.
mary
I normally wear pencil skirts with 2″ heels.
I have worn one particular skirt with crazy studded flats, but in general, I look better with a little lift.
Look at the shoes of Kate and Meghan (Duchesses!). The skirts are below the knee but their hoes are sky high.
TX-IHC
I have the Philosophy ponte pencil skirt from Nordstrom Rack in four colors I love it so much! It’s only $17. TTS. It does have a small exposed back zipper though which I know Kat is not a fan of, but doesn’t bother me.
Opal
I love Eloquii pencil skirts. Being blessed in the hip department I like the Viola fit.
PJ
Land’s End and Talbot’s have great ponte pencil skirts.