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Beauty & Fashion

Top 5 Winter Dresses to Keep You Warm and Stylish

It’s easy to forget about cute dresses during the winter months. The cold season doesn’t seem to render as many smart dress options in stores, and wearing pants and a sweater is often more comfy–something everyone can agree is important when you’re chilly!

But for those occasions when you need to wear a dress, or if you just really miss sporting them, we’ve rounded up five of our favorite winter-friendly dress finds. Remember that you’ll still need some thick tights or leggings and a sweater and jacket to stay warm. And, if you live somewhere really chilly, maybe a scarf, hat and legwarmers, too. Stay warm out there!



The shirtdress is a popular and chic way to stay both warm and comfortable. This particular dress, from Forever 21 ($25), is woven and lightweight. Little silver buttons and a light blue tie belt complete the look.


We can thank noted fashion designer Diane von Furstenberg for her brilliant wrap dress design. It caught massive popularity in the 1970s for its comfortable and forgiving design; it looks great on all body shapes! We really like this gray and neon print from Old Navy ($25) for winter–you could try a cute white or yellow cami underneath for extra coverage!


This simple striped dress , known as a “shift dress”, is celebrated for its simplicity and elegance. The version pictured here, from the Gap ($60), has the added bonus of being made from jersey. Super comfy (100% cotton!) and easy to accessorize!


We really love the color of this sweet and romantic ModCloth ($55) dress. The super great thing about this website is it offers free shipping and returns, so if you don’t like what you order or it doesn’t fit, you can just ship it right back!


We kind of want to curl up in this long-sleeved Merino wool dress and take a nap! It looks like a giant sweater, but is cut well and is both stylish and simple. Our favorite part? It is handmade by an artist on Etsy ($26), so you can be sure that it will fit!

What types of dresses do you like wearing during the winter? Take our poll and let us know which of our picks was your favorite–and comment below with more details!

What kind of winter dress do you love?

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Image: Thinkstock.com


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  1. Shanell Elise is back

    Posted by Shanell Elise is back on March 15, 2013 at 08:04

    I think 2 and 4 or really cute and my style. 🙂

  2. Nicolemariev

    Posted by Nicolemariev on February 1, 2013 at 21:00

    I feel like these are all spring or fall dresses. lol. I guess adding leggings helps, but when you live in NYC, it can be really cold! These are the kind of dresses I’d wear in 50-60 degree weather.

  3. Rbubbles

    Posted by Rbubbles on January 25, 2013 at 17:47

    I really like the last one!! I need a new pair of black leggings, but, i think that the last dress would go perfect with leggings and a little belt! 😀

  4. risingsunsets

    Posted by risingsunsets on January 25, 2013 at 10:40

    Your second and fourth dresses are too immodest.
    On the second one, I can see halfway down the model’s cleavage. It’s a good thing she’s small chested, or we’d be getting more than that.
    And I noticed the fourth one on a form, not a person. I know how shaped cutouts of people are shaped, so I know if someone put that “dress” on, it would be well above her thighs. Not to mention, it’s very see- through.
    The third one, I’m only marginally pleased with.
    Please try to do better, PI.

    • Grace Pierpont

      Posted by Grace Pierpont on August 7, 2013 at 08:45

      And they are all to short!!! If I’m going to wear a dress or a skirt it Has got to cover my knees. Standing or sitting.

  5. Uchiha_Kaida

    Posted by Uchiha_Kaida on January 25, 2013 at 08:19

    even though I’m not big on stripes or dresses I like the black and white stripped one desu~

  6. Project Inspired

    Posted by mrsminor2006 on January 21, 2013 at 22:07

    I like the dress at the very top with the young woman sitting on the bench. Now that is Modest! But still cute and can be accessorized with jewelry and etc. (Which of course is not necessarily needed) Love it! 🙂 I agree with the other comments about the dresses here not really being modest unless tights or pants were worn underneath. I personally don’t like wearing tights under every Dress. I mean gee, I want to wear a dress not so many different pieces of clothing. You know one thing I don’t like as a young woman is that it IS so hard to find long dresses and then even if they are found, it’s considered Not Cute by society. But hey, were here to please God not man. 🙂 MikaRose has some cute dresses that cover the knees.

  7. Project Inspired

    Posted by Dancer619 on January 18, 2013 at 06:19

    I love the third and fourth ones!!!!

  8. Paris

    Posted by Paris on January 17, 2013 at 18:23

    The last one is my favorite because it shows your curves without being to risque! I still love all the dresses,though. 😉

  9. ruthie27064Him

    Posted by ruthie27064Him on January 17, 2013 at 15:07

    I like the shift dress, but the rose one would look better on me. They’re all really cute though!

  10. HurricaneMurphGirl

    Posted by HurricaneMurphGirl on January 17, 2013 at 13:22

    So, I was wondering if you might do a post about shopping for cute stuff on a budget. Some of us don’t have $60 to spend on a dress, so I think it would be cool if you would do a post where all of the dresses were under $30. Just a suggestion. God bless!

    • AllisonGrace

      Posted by AllisonGrace on January 17, 2013 at 16:22

      Three of the dresses are under thirty! (By the way, look at the forever 21 dresses online. Cheap, modest, and super cute!)

      • HurricaneMurphGirl

        Posted by HurricaneMurphGirl on January 17, 2013 at 19:39

        I know, and I do like Forever 21, (although some of their stuff is too short, which can be fixed with leggings) I was just thinking it would be neat if she would do a post where budget was one of the main focuses.

  11. Eurydice

    Posted by Eurydice on January 17, 2013 at 11:27

    I don’t really care for any of them…MAYBE the wool dress, but the rest are just not for me at all.

  12. IdaPahus

    Posted by IdaPahus on January 17, 2013 at 11:22

    I love all the dresses, but especially the last one. It looks so comfortable!!!

  13. lotr1997

    Posted by lotr1997 on January 17, 2013 at 11:21

    I don’t want to come across the wrong way, but none of these dresses are really modest. If an average height teenage girl were to sit down in one of these, the young gentlemen would certainly get an eyeful. Maybe post some that are a little longer please?

    • texasgirl

      Posted by texasgirl on January 18, 2013 at 09:55

      Ikr? Dresses are getting shorter and shorter. 😛 I like to wear skinny jeans under dresses like these.

    • AllisonGrace

      Posted by AllisonGrace on January 17, 2013 at 16:21

      The shift dress, the wrap dress, and the dusty rose ones are modest… Also, she said to wear leggings with them. You and I probably have different views of modesty, but all of these are cute and appropriate!

    • bethluvstheafters

      Posted by bethluvstheafters on January 17, 2013 at 15:25

      True. But that’s why you accessorize them and put leggings or tights underneath. Plus it seems to be the easiest way to do things since there are hardly any cute dresses that are long enough out there anymore. 🙁

  14. Grace014

    Posted by Grace014 on January 17, 2013 at 10:23

    I actually own the Old Navy wrap dress in a green pattern, and I really like it! For winter, I pair it with a cardigan, infinity scarf, leggings and boots. 🙂

  15. MeghanHug99

    Posted by MeghanHug99 on January 17, 2013 at 08:50