Reader Request: Layering with Dresses

Reader Christine sent me this plea:

One of the things I’ve accepted about my body is that skirts and dresses are better. But sometimes it’s hard to find them, and then to figure out how to layer them. I love sleeveless dresses but then it can be hard to figure out what to wear if it gets cooler; a light cardigan in spring, a fall jacket in fall, but then … what are the most versatile dresses. Also I’m in my mid 40s so the leggings look isn’t much good for me.

Fantastic question, doll!

I shunned dresses for ages, believing them to be far too stuffy and formal for my business-casual lifestyle. But somehow I got swept up in the whole “day dress” revolution, and over the past few years, I’ve become addicted to them for the same reasons as Christine: They just WORK for my bod.

When my interest in wearing dresses was first rekindled, I set out to enlarge my collection. First stop: Savers! Quickly discovered that most of the frocks available at my beloved thrift shops were sleeveless. And I thought, “OK, all these sheaths must’ve been donated by fellow Minnesotans who finally accepted that, since we get six months of winter, sleeveless frocks ain’t practical.” But once my search expanded to the mall and Internet, I noticed that most retailers offer mainly sleeve-free frockage, too. And I was baffled. Sleeveless sheaths in the dead of winter? For really, BR, J.Crew, et all? Do you think we ALL live on the Equator?

But since they were all that I could find and they DID look pretty smokin’ on me, I slowly amassed a collection of sheaths. And, with a little experimentation, I found them to be truly versatile pieces. A sleeved dress is a ready-made outfit, and that is a grand thing when you need something quick and dirty. But a sleeveless dress allows for layering and accessorization, which means your creativity can run rampant. And I loves me a little rampant creativity.

I had bales of fun raiding my outfit archive for layered dress looks, and picking out my faves. Here are a few suggestions for layering with dresses to get us started. I have focused mainly on sleeveless sheaths, as they comprise the bulk of MY collection, are generally the easiest to procure, and truly are versatile little beasties. But I’ve got a couple of sleevers in there, as well.

And, as always, this is just to get us started. I do hope you’ll all chime in with more dress-layering ideas!


My current favorite look, hands down. Works fantastically well with a sleeveless sheath and a fitted, cropped blazer. Depending on your proportions, you could also try a sheath with a swing jacket, a sheath with a boyfriend blazer belted over it, or a sheath with a military-style blazer for a really funky look.

These are both recent outfits, but I’ll definitely be rocking this look come the cold. Add tights and tall boots, maybe a cozy scarf, and the combination is instantly winterized.


Oh, bolero. How I love thee. Let me count the ways.

OK, don’t let me count the ways, that’d be massively boring. INSTEAD! Let me just say that a nice curved-hem bolero is fantastically enboobening for those of us smallsters, and provides a less buttoned-up look than a blazer when paired with a sheath.


I feel like this is a look I am yet to truly master. To me, a dress/cardi combo SCREAMS 50s secretary, as evidenced by the pearls-and-buttons themed ensemble and sweater-clip deployment shown above. But I’ve seen sheer cardis belted over dresses with grossgrain ribbons and pinned with silk flowers, which makes for a delightfully romantic look. For those with the right proportions, a belted long/grandpa cardi can look chic and mod as well. And I’m sure there’s more. Suggestions?


These are some blanket-wannabes, I realize, but I just love the look of a sleeveless sheath with a bulky wrap for transitional seasons. Draping over the shoulders works equally well, and provides more warmth than either option pictured.

Adding a scarf or wrap to your dress-blazer or dress-bolero combination adds warmth and interest. Also, scarfing it up can make those other layers seem less severe and structured.


Yeah, so, ponchos DEFINITELY aren’t for everyone. And the itchy, be-tassled kind that we all the rage in the 70s are not generally advisable. But ponchos certainly are conversation starters! And a sleek, sweater-y one like this, combined with a sleeveless sheath, makes for a great transitional outfit. Or a great they-turn-up-the-AC-in-my-office-to-snot-freezing-levels outfit.


The boatneck is key, here, as it lets the dress peek out near your collarbone. A cowl, turtle, or crew will hide dress straps entirely, creating the appearance of a skirt-sweater outfit. Which isn’t a crime, of course, and can be fantastic in colder climes! More layers = toastier femmes. But since we’re talking layered dress looks, I’m focusing on boatnecks which let the viewer SEE that you’ve paired a sweater with a sheath. A sheer sweater – like this loosely-woven Eileen Fisher jobber I’ve got on – is even better as the dress will show through, subtly.


I wear my jean jacket like a blazer, and have a little cropped army-green jacket that gets the same treatment. Even a leather jacket could pass for a blazer if paired with the right dress. Something boyish or rugged looks fantastic with a girly frock, like my eyelet sundress here. Variations can be created for spring (leather jacket and floral dress with boots), summer (jean jacket with sundress and sandals), and fall (army jacket with sweater dress and boots).


Ah, the elusive sleeved dresses make their appearance!

Letting a sheer dress or colored slip peek out from under a more substantial dress is a great way to create interesting, warm, funky layers. That specific sweaterdress outfit got trotted out at LEAST ten times last winter.

But you can also layer a shirt dress over a sleeveless dress, as shown in the second photo. I prefer this look with a long-sleeved outer dress – often belted over the inner dress – but shorter sleeves can work, too. This is a great trick for dresses that hug a little too tightly: Let them peek out as an underlayer and utilize a thicker, more forgiving dress on top.

Now, I must say that I don’t generally condone turtlenecks beneath sheaths. It gives off a decidedly schoolgirl vibe which turns me right off. Even a crewneck tee shoved under a sheath can look awkward and dowdy. I vastly prefer that added layers sit atop the dress … although I definitely wear tees and longjohns as my base layer in January. I just don’t let them show!

Over to you, kittens! Are you addicted to dresses? Got a few sleeveless frocks and classic sheaths hanging in your closet? How do YOU layer them up for variety, style, and warmth?

P.S. Hi, my name is Sally, and I’m a pink-and-black-aholic. Geez, man.


    You are so adorable Sal…luv you in bright colors! I'm into big loose summer cardi, but trying hard not to look sloppy…

  • Christina Lee

    hello pink and blackaholic- from grey and blackaholic (more bland than yours)- i think you showed it all perfectly. I'd only add that I am forty and wear leggings- I think she should still give it a try-just keep it simple!

  • Oranges And Apples

    I love this question! I wear a lot of layers ('tis cold here in scotland!) but maybe not that many layered dresses. I will have a look in my WR set and maybe do a post on this too. I usually put long sleeved tees under stuff, which I don't think you've covered here. I've also layered shirts and dresses in the past, with the shirt underneath. Yes, maybe i will do a post on this!

  • Lemondrop Marie

    I have just started to really embrace and wear dresses more than any other outfit staple- especially an a line or wrap dress. I don't know why I never did before- they are far more comfy than I gave them credit for and more flattering on my height challenged figure. I am glad you did the dress over dress portion of this post, that is one I can never do well enough to leave the house confidently- maybe it's that height thing again!~

  • Christine

    I don't wear sleeveless anything, but I do have a couple of sleeveless sheaths in my wardrobe. One is charcoal grey, and I love wearing a classic white blouse under it, with some colorful accessories. Or sometimes a coloured blouse. Or a plain t-shirt (but the collar does look best). I know this look is very traditional, and not for everyone, but I'm a classic girl, and it's one of my favorite looks.

    Great post, btw.

  • Cynthia

    Oooooh! Loving that poncho look. Loving it.

    And you can add me to the list of pink-and-blackaholics, as well as the lesser known list of pink-and-greenaholics (hey, don't knock it till you've tried it – think: flowers.)

  • smaro

    I like the denim jacket and white dress combo! I have a few sheath type dresses but I tend to wear sheer cardys over them that are quite fitted or I wear a suit jacket/blazer over. I tend to swing between 1920's cute or business like and ready for action. The other thing I like is to wear a thin silk polo neck in winter or a fitted tee or flimsy shirt under my dress. I sadly have no dresses for casual wear at present…need to work on that!! I find for a smallie like me, its hard to find a dress that suits and sits at the right length that doesn't also have extra fabric sagging around the hip or bust area.

  • Make Do Style

    Love a dress and good tips but I don't understand why leggings are ruled out by your enquirer – they also give more options. The only reason people get into trouble with leggings over a certain age is they forget to think about proportions. I've got a couple of short dresses which in winter get lots of wear with tights but on a cooler summer day can be worn with just below the knee length leggings and flats in the day or longer or same length and heels in the evening.

  • hillary

    The dress over dress combo still eludes me. I have yet been able to do it successfully. Kimberly does a nice shirt over dress combo I like and want to try. I never thought ponch over dress! clever.

  • Audi

    These are some killer looks. I don't make enough use of the dress + blazer combo, but you've inspired me to try it.

  • Linda

    I'm racking my brains trying to remember whether I still have that pink boatneck sweater somewhere or donated it, with the possible result that you are WEARING MY SWEATER.

  • lisa

    Oh these are all such adorable looks! You always give such great advice, Sal.

    I have sleeveless sheath dresses and spaghetti strap dresses that I like to wear with long-sleeved or short-sleeved cotton tees underneath. A short-sleeved cotton tee under a strappy sun dress makes it a little less revealing, while a long-sleeved tee keeps my bare arms warm in winter. Plus, I can always switch up the look of my dress by wearing a tee in a different colour!

  • Sal

    Linda: HAH! Under normal circumstances, I MIGHT be wearing your pink boatneck … but I actually bought this one new. For once. 😉

  • Sharon Rose

    Hi there-this is a fabulous post and I only posted a few days back about dress dilemmas!! This really answers some questions for me too, so thanks for sharing!!

  • budget chic

    I love all your boots, you just reminded me to get some mid ankle cowboy boots this winter. I love your style…..simple, pretty and cute! You layered but you did not "over" layer. Somethings I see layering that gets out of control and it looks like the person has half their closet on.

  • MrsM in MI

    My favorite thing to do in the winter is layer a black turtleneck, black tights, and tall black boots under a colorful or patterned sleeveless dress. I sometimes will do the same thing in grey or navy but black just lets the dress stand out so well.

  • Kasmira

    Sheer, lace, or very lightweight blouses work under a dress. I've done this with both sleeveless and strapless dresses.

  • Nadine

    Thermals underneath! And/or slips.

    Dress with tights and boots, dress over jeans, dress over leggings, waistcoat over dress, dress with scarf, dress with fitted cardi, dress with oversize cardi, dress with bolero, dress over lace dress, wrap dress over dress, jersey (sweater) over dress, dress over hooded tee, jacket over dress, shirtdress over dress, tee over dress, dress over dress . . .

  • emily

    i also wear tops under/over the dress, so it looks long-sleeved/like a skirt.also, a skirt over the bottom of a dress makes a great top. :)

  • fashion herald

    I love you in the dress on dress, and dress/scarf! Of course, you are a dress girl so they all look good, but it's great how you find looks that suit all tastes.

  • Anonymous

    Wow, thanks for the great post Sally, and everyone for the great comments. I'm the Christine who pleaded for help and I now have a lot of great ideas.

    Makedostyle, I don't know what my issue with leggings is…I just feel weird wearing them. I think it's because I did that look in the 80s, when my legs were slimmer so I feel I shouldn't do it again.

    Same with wearing t-shirts or blouses under dresses…I should try it again too, but I always think of my school uniform!

    I'm really interested in trying the "dress over dress" idea though it makes me nervous. Thanks for the suggestions Sally. Time for me to play in my wardrobe and see what I can do. If I get very brave, I'll send some shots in.

    Christine xo

  • Sal

    Christine: YAY! So glad this was helpful, my dear. And I think I speak for us all when I say we'd LOVE to see some photos. 😉

  • The Budget Babe

    i love this post, so fun to see all the different ways you rock the sheath. i'd like to see you rock them with bare arms a little more, too, a la Mrs. O – yes you can!

  • Nina (Femme Rationale)

    i've shunned dresses for the longest time, too. but for some reason i find myself wanting to wear them more lately. i love your choices of cover-ups…def. going to use some of your outfit ideas.

  • WendyB

    Every outfit looks great! And yes, you are addicted to pink and black, but if it looks great, why not?

  • FashionAddict

    Great post! I wish I could rock the sheath, but I've got a little too much love in the handles, and they never seem to fit right.

  • Mary Sailors

    Great post Sal! I LOVE, love, love the pic of you in your little army boots, very cranberries, very urban dress! YOu're inspiring me to shop in my own closet! 😉

  • Bridget

    The woman behind The Uniform Project has a lot of ideas about what to wear with dresses…some may be slightly unpractical, but it's great for inspiration! (and man…I want that dress!)

  • metscan

    I find the dress + cardi combination most flattering on you. Have you tried a dress with a pashmina yet ?

  • ambika

    I need to try the dress plus other dress method. I'm always drawn to vintage slips for giving that same look but have yet to actually buy one.

  • GinaR

    The layering looks you put together look great!


  • Anonymous

    hey i just wanted to say that i always wear dresses with t shirts underneath. the lokk amazing and dont hide your dress but instead add to the dress. if you are very skillful you can use a t shirt to bring out certain colours in the dress or to makeit look different. i often wear white under a dress in the day and black in the evenings. really enjoyed the article. i also think that if you dont look good in legging wear bright opaque tights. these look very playful but look good on everyone wat ever your age and also they dont make your legs look short! rebecca x

  • Eyeliah SS

    Great collection of options, I ill try with the jean jacket belt and nice shoes (I say nice since I cannot wear heels), very cute!

  • Charlotte Drene

    You know, it is so nice to see someone wearing bright colours!

  • Kristin

    What fabulous style. So into the oversized scarf with scrunch boots!

  • musie

    Those combos are really cute. I wear dresses year-round, and generally do the following:

    – wear a low-cut dress with a tank-top underneath for warmth/neckline coverage/cute contrast.

    -wear a cardigan on top– this can be made less-buttoned-up through careful tweaking of necklines, so the line isn't awkward. There are ways to make it look really cute!

    I'm wearing this particular combination right now… my office is frigid, but it means I can easily change into a cute dress when I'm done with work for the day.

  • Oranges And Apples

    hi, as you know, I did go and post about it, here's the link:

    There was quite a lot of scrolling down involved, you are such a productive blogger!