Reader Request: Summer Dresses in Fall and Winter

Reader Sarah wrote in with this plea:

I have a lot of sundresses (spaghetti straps, v-necks, pretty flowers) but very few fall/winter dresses, because until now I’ve gone into hibernation mode–jeans, uggs, sweaters. No more of that for me! But I am a broke college student and cannot afford to revamp my wardrobe all at once. So, my question is: How can I take a sundress and transform it into something appropriate for fall/winter without just looking like a girl trying to wear a sundress in the winter?

In years past, several style “rules” would’ve forbidden a summer dress from remaining in rotation during cold weather. Florals were generally reserved for warm weather, as was white. But now? Those rules have been chucked, and your options are broadened. Summer dresses can be worn in mid-January in looks as varied as they are chic.

In my opinion, though, there are still a few things to avoid when transitioning your summer dresses to fall and winter wear.

What NOT to transition:

  • Pastels may trend for cold-weather wear, but styling them can be tough. Use them sparingly.
  • Cotton voile, linen, or any other super-summery fabrics may look awkward.
  • Careful with those spaghetti straps. The dresses can still get used, of course, but make sure the straps are covered.

Other than those restrictions, it’s a free-for-all. Any dress that has even the slightest chance of working effectively in a layered ensemble is fair game!

How to transition:

  • The simplest way to make a summery dress work when it’s nippy but not freezing is simply to throw on a pair of opaque tights and some boots or booties, as I’ve done in the photo above.
  • Don’t think of your sweet summer frock as a dress exclusively. Try layering a cowl or v-neck sweater on top and letting the dress function as a skirt. This is especially fun and effective for dresses made from beautifully textured fabrics, or printed with gorgeous patterns.
  • A top layer like a blazer or cardigan works wonders. Belt underneath that top layer to define your waist, if you so desire. Add tights and boots and be done!
  • Make the sundress the bottom layer of a many-layered outfit. Start with tights and boots, add your sundress, then layer another skirt on top of the dress (preferably a full and/or drapey style), and top it all off with a sweater and/or blazer. The sundress will basically just be a little bit of texture and print/color peeking out from the hem of your outfit.
  • With shorter dresses, just treat them as tunics. Layer atop slim jeans or leggings, and boots. Add a cardigan for warmth when you need to.

Personally, I am NOT a fan of putting a turtleneck under a dress. Some ladies love it, but I say avoid!

Originally posted 2009-10-21 05:41:00.

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33 Responses to “Reader Request: Summer Dresses in Fall and Winter”

  1. Cupcakes and Cashmere

    all fabulous selections (particularly the bit about pastels). i think pretty much anything else can be transitioned to winter nicely with some opaque tights and boots!

  2. RML- Being More Through Having Less

    I am exploring leggings this winter and trying to get some wear out of my summer dresses that way.

    Adding more wintery looking belts is an option too- creates a new silhouette as well 🙂

  3. K.Line

    You know, in the past I wouldn't have tried to bring the summer dress into the winter. But I'm branching out and I do love tights. I'm going to give your suggestions (esp. the sweater over top – lord knows i have enough of them!) a try…

  4. Clare

    Oh, so glad you did a post about this! I think so many of us are willing to shun our summer dresses to the attic (basement, large box in the closet, whatevs) when winter rolls around. And I'm actually a huge proponent of the turtleneck layering thing, but I agree that it's not for everyone. I think I like it on me because it plays into the '60s pixie look with my hair and build.

  5. Erica

    I've started doing this a lot lately to make the most of my wardrobe (thanks, recession). I disagree about turtlenecks. I would say, yes, avoid plain cotton TNs, but ribbing and heavier weaves generally look more adult. And I find that pastels look more approp in the Fall when accented by warmer, bolder colors like burnt orange, maroon, mustard yellow …

  6. gina

    Great suggestions! I also like turtlenecks under dresses. In addition to turtlenecks, you can layer long-sleeve tees, crewneck sweaters and blouses underneath dresses. Once you have a layer (or more) underneath for warmth, you can stop there, or add another layer on top such as a vest or blazer or short-sleeved jacket.

  7. futurelint

    I think you nailed them all! I'm all about the cardigans, boleros, and blazers over summer dresses. I'm also loving that it's now stylish to wear boots, tall socks that peek out, and tights all at once! Generally, if my feet are warm, so I am I, even if I'm wearing a dress on those negative degree days!

  8. Meli22

    It won't be very feasable where I live- we can get several feet of snow in one storm. NOT skirt/dress friendly…

  9. SR@MyStyle

    Hi there-that's a really good post and very inspirational for ways on getting the most out of your summer dresses. I'll be wearing some of mine with opaque tights too and I like the idea of wearing them as skirts with jumpers over the top-thanks my dear!

  10. spacegeek

    How would you do a wrap dress with another dress under it? I have a black sweater dress that I think would work under a floral wrap dress, but I'm wondering if the whole thing will just make me look wide… guess I'll have to try the combo on!

  11. lisa

    Great advice on a very timely topic! I have one Topshop floral sun dress I love to wear layered in the fall and winter. A white V neck tee underneath and a black cardigan on top go a long way to making it season-appropriate (see here).

  12. Sal

    spacegeek: Do just try experimenting. The underneath dress will need to be fairly snug for that kind of layering to work … but it can work!

  13. Mrs.M in MI

    I also have to disagree on the turtlenecks. My favorite way to winterize a sleeveless sheath dress is a slim black wool turtleneck with black tights and black boots underneath. I do agree that any other type of turtleneck looks too school-girl, though.

    To winterize less-structured jersey dresses I pop a warm belted cardigan over the dress and tights and boots underneath (plus long underwear – this is Michigan).

    I do appreciate the layering suggestions and am now thinking of ways to make my dresses skirts or tops!

  14. Work With What You've Got

    It never really gets all that cold here to be honest. I don’t think I have a single dress I can’t wear year round with the addition or subtraction of some things. Even the most floaty summer dress can be worn here dead winter, with tights, leggings, socks,. Boots, a cardigan and a jacket!~ I’m just lucky that way!~

    But I wouls say my biggest trick is tights, under leggings, with thick socks, in boots. Warms the bottom layer right up (but not enough for some pleaces!)

  15. Audi

    Great tips, Sal! You're right on target with these. The only dresses I don't use during the winter are the soft, pastel colors, unless it's just a tiny bit of the fabric peeking out beneath another layer. But then again, I usually need to layer up my summer dresses even in summer with our wacky weather.

    Also, this Friday's post has me wearing a turtleneck with a dress. I don't think you'll find it schoolgirlish, though. 🙂

  16. Nadine

    I never observe any seasonally-related colour guidelines (possibly because I'm not in the States). So I DO rock the pastels and muted tones – the trick is to wear coloured opaques. Black opaques can kill an outfit stone dead if the dress is a soft colour.

    To wear dresses in winter I go with tights, long-sleeved thermals and a slip (full or half) underneath, and a wool jersey (sweater) over the top. Add jacket as required. The other option is to wear a slimline jersey UNDER the dress – best for big 'feature sleeves' or fuller-cut tunic styles.

    I'm delighted about anyone else wearing turtlenecks under their dresses, but I don't do it myself (it's a short neck thing).

  17. Meli22

    hey sal- unrealated topic here.

    I came across this blog today

    She's a woman who is terminally ill, due to 22 years of an eating disorder. She developed it after being abused.

    I thought it might be interesting with the body image talk we often have here.

    warning- very emotional and sad

  18. Make Do Style

    Yep layering, tights and boots plus my personal fav arm warmers!

    You put it very nicely about polos under dresses.

  19. issa

    great post.. i'm looking forward to transitioning summer dresses to more fall-like outfits.. once the temperature gets cool enough to layer.

  20. Luinae

    REALLY great post, I can't wait to try out some of these tricks. I have to try wearing a sweater over a dress, I have some that would be perfect for them.

  21. Hammie

    I like see-through summery dress fabrics with a black long sleeve tee and a vintage style slip underneath. But thats just me maybe?

    This post is exactly what is on my mind at the moment. I love wearing dresses, but a lot of winter dresses are crap (and too expensive at the moment) so this is a good compromise. Must admit I really hate tights though, leggings and socks for me. xx

  22. MP

    I can't wait to try this out this winter. I have to say that I've always worn my summer skirts all winter; the bright colors due wonders on a grey winter day!

  23. AsianCajuns (Lauren)

    I do keep some of my summer dresses in rotation, but I usually wimp out in cold weather and pull on pants. I agree with you, Sally- no turtlenecks under sweaters! Being a shortie, anything that makes me look more school-girlish is a big no no.
    Hope you are having a wonderful week, lady! Still loving those payless booties on you (and I get all green with envy when Cath has them on too ;).

  24. lopi

    Couldn't have said it better. I never put away my dresses, as they are both summer and winter wear. And may I add, a generous scarf is always a nice way to hide a too-revealing neckline and a nice alternative to halternecks when trying to keep warm.


    Great tips Sal!
    My working space can get too warm from the the heater…I invest on great coat for outdoors!

  26. poet

    Good points! Just one critique: In my experience, a slim v-neck sweater works under a spaghetti strap dress if both are classy enough. Or if you're lucky, you happen to have a long-sleeved shirt in the exact same color as the strap dress and it looks as if it was one piece even when the shirt is worn underneath the dress…

  27. enc

    Sort of a moot point for me, as it never gets "cold" here, but I think the point about topping a dress with a sweater is a great one, because it adds life to solid-colored or non-seasonal patterns (tartan, plaid, check, stripe, etc.)