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Fashion Challenge: Wear a Summer Dress in the Winter


Girl wearing a dress in the snow

As you all know, we like to focus our Fashion Challenges on creatively combining pieces you already have in your closet. Finding new ways to wear things you already own is a fashion win-win — not only are you getting more from your existing wardrobe, but it forces you to think outside the box and develop a knack for creating new outfits. This week, our challenge for you is to take your favorite summer dress and make it work during the winter.

Dreary winter months can leave you feeling “blah,” especially in a sea of muted colors typically associated with chilly weather. A splash of color sometimes is all you need to brighten up your day. So dust off your box of summer clothes and find a dress you love — then read on for a guide on how to take this week’s challenge!

Tips and Tricks for MakingĀ  a Summery Dress Work for Winter

  • When selecting a dress for this challenge, look for bold colored frocks - they’ll make the biggest impact in winter.
  • Pastel colored dresses can work, too — pair one with dark accents to make it feel more wintery!
  • Wear a summer dress with tights or leggings. It’ll keep your legs warm and make the dress look more seasonally appropriate.
  • Consider the print of the fabric. Plaids and stripes will work nicely. Floral prints will work most of the time, but stay away from Hawaiian prints unless you’re sartorially fearless.
  • Try a summer dress on with a pair of boots to keep your feet warm and toughen up the look.
  • Throw on a jacket or cardigan on top of a dress for warmth and a touch of layering chic.
  • Another way to add warmth and change up the look of a dress is by layering a long sleeved top or turtleneck underneath a strapless dress.
  • One more way to update a dress is by pulling a sweater on top of it, transforming a dress into a skirt.
  • Accessories are probably the easiest way to transform a summer dress into a winter one. Add a beanie, knee or thigh high socks, or a scarf.

Outfit Inspiration

How to wear a summer dress in winter - outfit 1
Dress, Cardigan, Boots, Tights, Scarf

The deeper tones of this floral dress make it work for all four seasons of the year! Add interest by layering a cardigan on top and leggings beneath. This outfit will look great with a pair of lace up boots and an infinity scarf!

How to wear a summer dress in winter - outfit 2
Dress, Boots, Jacket, Tights, Earrings

A pastel dress can work in the winter as long as it’s paired with wintery elements. I love the contrast of a girly pink dress paired with a tough a leather biker jacket. Patterned tights and combat boots give this outfit a punky British fashion feel. Finish with chic earrings.

CF Reader Looks

Here are challenge outfits sent in by CF readers like you. If you want to see your look featured here, too, read the instructions below for sending in your outfit photos!

Kyrstin – York University

College Fashionista from York University

I’m wearing my favourite summer dress here, despite the fact that it is January. It’s a bit short, so I opted for leggings over tights. I belted a cardigan to accent my waist, and added my favourite tall boots to keep warm! I love wearing bright colours in the winter – it’s a change from the usual all-black uniform!

For more of Kyrstin’s fierce style, check out her blog here!

Laura – Elon University

Elon University fashion

This is one my favorite dresses I’ve ever worn. All the girly elements, the pink, the ruffles, the tulle, just called my name and I feel incredibly feminine while wearing it. I love it so much that I can’t just let it hang idly in my closet through all the cold months. Thank goodness for the invention of the cardigan- a dress lover’s best friend. Belting this cardigan keeps my waist defined and the heels add a little edge to an otherwise over-the-top girly ensemble. Tights were a must to battle the winds of Philadelphia and I kept the jewelry simple so that the focus of the outfit remains on the dress.

For more of Laura’s chic style, check out her blog here!

Took the Challenge? Send Us Your Look!

Did you dust off your favorite summer dress and make it work for the cold time of year? Before you change, take a couple pictures and send them to fashionchallenge AT along with your name, school, a description of what you’re wearing, and your blog URL if you have one. We’ll feature your pictures here to inspire other CF readers (see examples here and here).

We can’t wait to see your outfits!


What are you favorite dresses to wear year-round? What other summer pieces do you like to wear in the winter? What future fashion challenges would you like to see? Leave a comment and tell us what you think!

Posted on on January 27, 2011 / Filed Under: Fashion Tips / Tags: , , , , ,

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29 Responses to “Fashion Challenge: Wear a Summer Dress in the Winter”

  1. 1
    January 27th, 2011 at 11:32 am

    I do this all the time! It’s all about layering layering layering, and is kind of a no-brainer as long as you have the right pieces to work with. Since it can get extra cold where I am, I’ve gotten good results in layering two dresses (the colourful hem of a floral peeking out from under a darker neutral dress), a pair of tights AND leggings, and cute boots that can accomodate warm socks, topping it all off with a warm cardi, pea coat, scarf, and other warm accessories as appropriate.

  2. 2
    January 27th, 2011 at 12:28 pm


  3. 3
    January 27th, 2011 at 12:30 pm

    If I’ve got a short dress that could pass as a tunic, I’ll just throw a pair of jeans underneath! It allows me to wear my sleeved dresses all year instead of just for a few months in the summer. Plus, layering is my BEST FRIEND. I’ll wear a thick cardigan and pea coat over basically anything and it’ll keep me warm!

  4. 4
    January 27th, 2011 at 1:14 pm

    what a great idea. i love this site so much, you have such awesome posts every single day. I’m totally going to wear a summer dress today!

  5. 5
    January 27th, 2011 at 1:20 pm

    Brilliant! I especially love the first outfit!! Most of my dresses are summer, but I wear them year round. I would love to see more outfit ideas for this. :-)

  6. 6
    January 27th, 2011 at 1:39 pm

    Thank you guys so much for featuring me! :)

  7. 7
    January 27th, 2011 at 3:08 pm

    I love this post and Kyrstin’s style! Do you know where to get good quality riding boots for about 50- 60 dollars?

  8. 8
    January 27th, 2011 at 5:24 pm

    This is a lovely idea!
    College, of course, is all about broke college students, so being able to reuse a dress year-round is marvelous!
    Thank you!
    And the ladies who tried it look lovely!

  9. 9
    January 27th, 2011 at 5:27 pm

    If you are a shoe size 6 or 9, you are a lucky girl!
    Urban Outfitters is selling some beautiful BDG part-canfas riding boots on sale for $50 that used to be around $100. Hurry!!!! Good luck!

  10. 10
    January 27th, 2011 at 5:32 pm

    One more idea.
    State Line Tack is selling REAL riding boots for around $40.||24323520746f20243530&sort=pricehigh
    The Devon-Aire pair looks very pretty. I’m not sure how comfortable either pair is, but they are very classic-looking and will probably last you a long time.

  11. 11
    January 27th, 2011 at 5:58 pm

    I love doing this in the winter. Even here in Minnesota I’m not one for conforming to the cold!! I always wear my summery dresses with a cardigan or a fur gilet to give them extra mileage!!
    Great post :]]

    Charlotte xxx

  12. 12
    January 27th, 2011 at 6:21 pm

    Thank you so much for featuring me guys! This is still my favorite fashion blog so I am a happy girl today!

  13. 13
    January 27th, 2011 at 6:21 pm

    So weird, I read this everyday and it seems like you read my mind sometimes! JUST last night I was thinking about wearing a summer dress but couldn’t quite get the shoes right. I think I have some ideas now. Thanks for the inspiration!

  14. 14
    January 27th, 2011 at 7:30 pm

    My roommate and I were just talking about how our winter wardrobe is basically just our summer wardrobe with a coat, scarf and boots! Love the first look!

    xo Leslie

  15. 15
    January 27th, 2011 at 8:31 pm

    Thanks Kimi! I love the StateLine pair & will probably order them !

  16. 16
    January 27th, 2011 at 8:36 pm

    I love dresses! they’re so cute and feminine… and winter is very chic!
    so, it’s a great combination :)

  17. 17
    January 28th, 2011 at 12:06 am

    How funny! I wore my white foral summer dress with brown booties, brown knee high socks, and brown cardigan today! The only difference with me and this post is that winter in Southern California was in the mid-70s haha.

  18. 18
    January 28th, 2011 at 12:19 am

    it’s -20 where I live, so I have to wear two (2!!!) pairs of pants to school…sigh. the blistering windchill should lessen about mid-March. until then, I am stuck wearing TWO PAIRS OF PANTS. sigh, again.

  19. 19
    January 28th, 2011 at 1:56 am

    it’s been -30 where i live lately. i rock this look a lot, def with leggings, a thick cardigan, thick circle scarf, thick knee highs hidden under thigh high boots and a long jacket.
    great post! the pink outfit is cute but heels are not practical at school haha. def cute though! x

  20. 20
    January 28th, 2011 at 4:08 am

    Very cute looks!

  21. 21
    January 28th, 2011 at 8:18 pm

    What about a maxidress? I have one in a sky blue (or baby blue).

  22. 22
    January 29th, 2011 at 5:34 pm

    I live in upstate Wisconsin and I’m rather notorious for wearing skirts and dresses every day, even through the bitterest of winters (and it can get pretty cold– it’s only 20 degrees right now, but it’s usually still -30 with windchill by this time of the year). I agree, it really comes down to layering. For example, I’ll wear something like black sweater tights with gray thigh high socks with a contrasting texture and don on my brown over the knee boots and voila! It’s super fashionable when contrasted with a bright, flowy floral dress but still incredibly warm. Great post!

  23. 23
    January 30th, 2011 at 12:26 am

    Deja- You should try pairing your maxidress with a sweater or your favorite flannel shirt.

  24. 24
    April 23rd, 2011 at 5:35 am

    I’m liking the first photo but the second one looks a bit out of place for my taste. Pastels can be hard to transition into winter. Some summer dresses do work whereas some look strange, you just need to see and know what combination works.

  25. 25
    July 14th, 2011 at 3:58 pm

    I love this trend! It is probably my favorite one to wear in winter and fall for that matter. I live in northern Minnesota and I hate dressing to look like a snowman when I go out and especially to work (I teach high school). This is the perfect way to stay warm and look chic:)

  26. 26
    December 22nd, 2011 at 10:43 pm

    OmG…I love this idea I have actually ordered a dress And it is very summerish…it is a short strapless black And white polka-dot with a red belt! I am planning on putting it with leggings And boots and a red long sleeve under!!! P.s please tell me if u have any ideas on what I could add or change to make it better! Thanks!!! :)

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