The Hunt: Stylish Work Dresses

stylish work dresses

2018 Update: Check out our latest roundup of classic sheath dresses 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.

The sheath dress: it’s one of the most stylish work dresses a woman can have, and if you buy the right dress, it can be a workhorse for your wardrobe, whether your office is formal or business casual. Get one that matches your blazer and wear it as a suit! Top it with a fun blazer (like this morning’s) for a more casual but still formal look, or with a cardigan or denim jacket for a more casual look.  Layer it in colder weather with a light jersey turtleneck, a crisp collared blouse, or even a long-sleeved jersey tee that best matches the neckline (or, ahem, raises it where it needs to).  It’s hard to go wrong with the sheath dress, but watch out for these pitfalls when buying it: is the cleavage too low? is the hem-length appropriate? does it have any trendy detail that will make it more memorable and thus less wearable in regular rotation (exposed zipper, embellishment at neck, etc)? is the slit too high? does it look “tailored” (good) or “body conscious” (less good) to you? is the back inappropriate for work? (In general, look for a high neckline in the back, not a scoopneck in the back or other “tank dress” type of vibe. Definitely nothing cut like a halter, at least for a traditional sheath dress in a conservative office.) Once you’ve purchased it: make sure you cut your vents. Hang it up immediately after each wearing and let it air out a bit.  If it’s part of a suiting set, be sure to dryclean all your pieces together so they show the same wear and tear. (While today’s feature is focused on sheath dresses, fit and flare dresses can also be workhorses; our last roundup is here.)

favorite work dresses

Hall of Famers, pictured above: one / two / three / four / five

Curious for past roundups of sheath dresses? Here they are from 2015, 2014, 2013, 2012, and 2011. For other sizing issues you may want to check out our last discussion on bespoke dresses, which you can order fit exactly to your measurements.

Pictured at top: Vince, Reiss, Halogen.

Note that even if a color is shown below, all of the featured dresses also come in black. 

work dress under $50 First up, this gray twill sheath dress from Target’s Merona brand for $29. It’s available in gray, black and navy; it has a matching blazer, and it has four star reviews (some reviewers had issue with fit).  There were a lot of affordable dresses vying for the top spot here (see how long our “under $100” category is above!), but I liked that this one also has a blazer. (The blazer comes in plus sizes, as do the matching pants, but the dress doesn’t seem to, alas — but note that the dress is available up to size 18.) Bi-Stretch Twill Wrap Sheath Dress – Merona™

(Target has a few other nice looking dresses if you’re there — this ponte sheath dress also looks nice and is highly rated (and I still wear the Merona dresses readers turned me on to years ago); this scuba sheath dress looks nice and has sleeves, and this fit and flare dress is also very tempting for $29.

work dress on saleThis Ann Taylor dress is part of its’ all-season stretch line, meaning it also has a matching blazer — and like everything else over at Ann Taylor today it’s 50% off, bringing it in at number two today. (I’m seeing tons of affordable, classic options today!) It’s available in regular, petite and tall sizes, 00-14 — it was $139 but comes to $70 with code CYBER50. (!!)  All-Season Stretch Seamed Sheath Dress

(A few other selections from the sale: this gorgeous sheath dress in light purple and green, the very popular Eryn kitten heels, and this large tote. If you, like me, are also craving a Chloe flap bag, this shoulder bag is an acceptable dupe.)

stylish feminine work dressA pink sheath dress can be a bit much, but you can really clearly see the seam detail here — and I like the seam detail.  (It also comes in black and a Claire Underwood-approved white.) As noted above, of course, a little detail like this may not be what you’re looking for if you have a very small wardrobe — it takes it from “building block of your wardrobe” to “geez didn’t she just wear that dress yesterday?” — but if you’ve been around the block a few times it’s also the kind of detail that can be a fun addition to your wardrobe. The dress comes in regular and petite sizes, 0-16, for $98; it’s fully lined and has a hidden zipper in back (huzzah). Halogen® Seam Detail Sheath Dress
vintage work dressI liked the look of this dress when we featured it in a dark green last fall — and I always take it as a good sign when they bring it out again in other colors, including black, cobalt, and (ooh!) a polka dot and a floral.  It’s too soon to call it a “Hall of Famer,” but I’m watching this one.  I like the sleeves, the deep V, and the semi-vintage vibe — for $138 it’s all pretty good.  It’s available in sizes 0-14 at Nordstrom. Betsey Johnson Puffed Sleeve Scuba Sheath Dress
modern classic sheath dress for workTheory is great (and their Betty is always a good choice), but for modern classic workwear, another brand to watch is Vince. This dress gets rave reviews, particularly as a packable dress (i.e., throw it in your suitcase and pull it out without too many wrinkles). It’s available in sizes XS-L. Vince Knit Shift Dress
designer work dressLast Call has some great sales on sheath dresses right now, including this lovely leather-trimmed number from St. John’s. I like the tweedy texture, the leather details, and the overall classic vibe (high neckline, high back, etc). They say to “compare at $1,045,” but today with various discounts it comes to $530. Nice. St. John Textured Sleeveless Dress W/Leather Trim

Like this feature? Check out other recent installments! And please feel free to Pin it if you like it!

Looking for stylish work dresses like sheath dresses? Check out some of our all-time favorites for wearing to the office and beyond!




  1. Calling all pears.... :

    Any sheath recs for pear shaped folks?

    • jumpingjack :

      I second this. And also for hourglass shapes.

      • Clementine :

        I like the limited for my hourglass shape. My coworker wears them and they look good on her pear shape.

    • Check out the Calvin Klein dress linked under “Hall of Famers” — also the link to our last discussion on bespoke dresses. I’ll throw a link in the article to our last roundup of fit and flare dresses for work, though — that may be easier hunting for you.

    • Slight Pear here :

      Not sure why Antonio Melani didn’t make the cut, but I love their work dresses. Reasonable prices for lined dresses.

    • The only sheath dress that looks right on my pear shaped body is the Limited Collection v-back. I hate that it’s not a normal back, but I still own four because it’s the only thing that fits my bottom and isn’t way too big on top.

      • Calling all pears :

        Thanks for this rec. I would have never checked them out otherwise. And I too will hate the V-neck back.

  2. Marshmallow :

    I noticed MM LaFleur didn’t make the list and wanted to ask if anyone else has had issues with their fit lately. I have several older MM dresses that are the workhorses of my wardrobe. I adore them. This winter I did a Bento Box and hated everything– way too slinky, body con, looked more for date night than the office. A few months later they came out with a new collection and I tried two new dresses: a 3/4 sleeve fit and flare, and a wrap dress. In my usual size, the fit and flare was way too large but the wrap dress was extremely tight. I keep wanting to love MM because their early stuff was such a hit for me and the quality is really there, but the inconsistent sizing is driving me nuts.

    • I’ve found my recent tops from them as being way too body conscious.

      I think they are tough to recommend because due to constant lack of stock.

    • I’ve tried the Tory recently and found it flattering, but some of the others have been tight

  3. I’m 6 weeks pregnant and unfortunately my spring wardrobe was due for a refresh, which seems sort of pointless now. I’m hourglass shaped and petite–any suggestions for less-constricting sheaths that aren’t necessarily maternity, but could work until I actually need to be in maternity clothes? I’ve tried many iterations of the Lands End ponte sheath, but because I have a large (and growing by the day) chest, I look like a human b00b in it since it has such a high neck.

    • I would opt for wrap dresses instead, especially if you plan on nursing/pumping after baby is here. Most sheath dresses are not going to allow for easy access. Plus, some experience some serious first trimester bloating, so while you may not be showing yet, you may also may not feel like zipping yourself into a dress in the event you do bloat.

      • Maddie Ross :

        I agree on wrap dresses, but (and this is a big BUT), if you aren’t telling yet, wrap dresses show all. So it can be a really early give away. I’d probably save the wraps for once you’re comfortable with people knowing. I think high waist knit dresses with a tulip skirt are the best in early pregnancy. They totally hide the bloat and are comfy over it, but are still pretty “normal” looking. Check out the “textured cotton dresses” or the “daybreak dress” at j.crew factory.

        • The daybreak dress would be perfect, thanks for the suggestion! I know exactly what you mean about wrap dresses–I have several, and they’re fine for now, but I think I’ll be self-conscious in them soon.

    • Lands End has a short sleeved wrap dress (short-sleeved ponte surplice) with a V-neck. I try to hide my not-too-flat tummy and it works well. I think it’s a different fit that the one described by Maddie Ross above.

  4. I’m looking at buying a used car. Right now I’m between a 2013 Toyota RAV4 Limited and a 2013 Cadillac SRX Luxury. Can anyone comment on either? I’d also appreciate any feedback on experience with either brand. The Cadillac is about $3k more but has 20k less miles and a V6 engine instead of an I4. On the downside, it gets about 18mpg versus 23mpg for the Toyota and to my limited knowledge, Cadillacs don’t have the same reputation for reliability as Toyotas. It just looks so nice!

    All comments are greatly appreciated!

    • I would definitely go with Toyota over Cadillac. Based on the small sample size in my office, Toyota greatly outlasts Cadillac with far fewer problems, cheaper routine maintenance, cheaper parts when something does need to be fixed, and less time spent (so cheaper labor cost) on repairs due to design. (In full disclosure, we own a Toyota Highlander and have been very happy with it.)

    • Maddie Ross :

      I think you have to do what you like better, realizing that all cars are subject to potential issues. I had a Toyota Camry where the engine blew at 95K miles. Everything I’d ever heard made me think I’d get well beyond 150-200K in that car. Not so. So buy what you like. Oh, and the more powerful the engine, the easier to drive on the interstate in my experience.

      • Slight Pear here :

        I’m sorry your Camry died, but reliability is an important consideration and anecdata doesn’t discount Toyota’s sterling reputation for reliability. That being said, I’d want to make sure I at least did certified pre-owned.

        • Maddie Ross :

          I know, I’m not saying my anecdote should weigh more heavily than anything else anyone said. The import of my statement was that she should get what she likes the best – realizing that no make or model is a guarantee of performance.

  5. Disconnect? :

    I know people here sometimes discuss eliminating social media connections to exes. I am still connected to my ex on LinkedIn. This person treated me horribly towards the end of the relationship. Even though we don’t speak anymore I have kept the LinkedIn connection–just because i.e. you’d rather have more connections than less. I am thinking of removing him completely, part of it is emotional I suppose i.e. it is someone I dislike. Is this petty or should I just keep the connection?

    • Shopaholic :

      I would remove the connection – do you really want to be connected to someone who treated you horribly? (although as I say this, I realize that I am connected to my exes on LinkedIn, including one who treated me horribly but I don’t really have any emotional ties and don’t really use LinkedIn like I use other social media)

    • Mary Ann Singleton :

      Just remove it. I removed my ex who treated me horribly so I wouldn’t keep seeing his name and profile pic pop up as a mutual connection – we’re in the same industry so we know a lot of people in common.

      Why not remove him and replace him with another connection? Look at the “people you might know” page and I’m sure you’ll find someone else to add instead.

    • Yes, disconnect. One less connection on LinkedIn is not even going to get noticed.

    • Slightly different point of view – Linkedin connections are pretty passive (in other words, you’re not likely to see vacation photos of ex and new person on there) & I prefer to know who’s connected to who and how – good or bad. I’d keep the connection so I don’t accidentally take a job with his biggest work cheerleader or something like that.

  6. Anonymous :

    Alas, sheath dresses just emphasize your belly in a very unfortunate way when you’re apple shaped.

    • I still love sheathe dresses, and they make me loose weight b/c EVERYTHING shows when you are heavy. FOOEY, but it does insent us to loose weight in our bellie’s and tuchuses. YAY!!

  7. mamiejane :

    I notice you almost never (maybe never) include JJIll in your roundups. I find they they great sheath dresses and their petite extra large fits very well. One problem with larger sizes for small people, especially sheaths, is armhole size. I find that JJill’s sheath dresses fit in a way that isn’t boxy. Here is one example of the kind of dress they have that works least for me. I probably have half a dozen of them and wear them to meetings and even Court (for motion practice) with a structured cardigan.

  8. Of Mercer is another good option, and made in the USA. I tried MM Lafleur recently and found the fit to be pretty good for me.

    • I agree with Alexis – love my Fifth Avenue Dress from Of Mercer ( MM was a little too straight for my body, but still nicely made.

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