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What Do I Wear There? Outfits for Cold, Rainy Days


What to wear on a cold, rainy day

Product Information: Marigold Raincoat: ModCloth, Pleated Houndstooth Coat: FredFlare, Pink Trench: Oasis, London Trench: ShopRuche, Cloud Umbrella:

I am not a fan of the cold. I also really dislike getting my beloved clothes and poof-prone hair wet. Therefore, the combination of cold + rain = a pretty unhappy me!

Unfortunately, cold, rainy weather happens, and as college students forced to follow rain or shine schedules, we have to endure it. This is especially tough if you live in an area like Jeanie, who posted a couple weeks ago about her cold/rainy weather worries:

I was wondering if you could post a section on rainy days. I live in Shanghai, so it rains a lot during the spring, winter and fall (practically every day!), and occasionally during the summer. I know that Zephyr already did a post on something like that, but it was for much warmer weather. I have a pair of rain boots, but I’m not too sure if they would be good for the winter as well. I was wondering if you could give some ideas on how to dress during the fall and winter for rainy days.

Since even my roommate asked me about what to wear on these dreary days recently, I figured this may be a question on many of your minds.

And while, as Jeanie pointed out, Zephyr did already write an article about rainy day fashion (which I definitely recommend checking out, she has some amazing tips!), I figured it may help some of you to revisit the topic in the context of fall/winter weather.

So here are my takes on the best base outfits for a cold and wet day.

As always, I have not added specific coats to each outfit, but I have put a few samples up top! They’re all trench coat shapes (I think these cover the most of your outfit and are therefore best for the rain) but range in fabrics from the waterproof, more light-weight yellow coat to the heavier wool houndstooth print jacket.

After the outfits, I’ve also included some “rainy day weapons,” or products that are essential to keep you look great in this weather!

Outfits for Cold, Rainy Days

Look One: Day-Time Showers

Cold, rainy day outfit

Product Information: White Tank Top: Wet Seal, Military Style Cardigan, Faded Grey Jeans: AE, Black Knit Beanie: TopShop, Red Rain Boots: Piperlime, Geometric Umbrella: Debenhams

Just because the weather is less than lovely doesn’t mean your look has to be!

Instead of going for the typical, structured military jacket, in this look, I chose a cardigan that has all of the great details of a military coat but none of the uncomfortable stiffness. Since the cardigan is black, it won’t change color or become see-through if it gets a little wet.

Underneath, I kept it basic with a plain white tank, which could be swapped with a tee-shirt, long sleeve shirt, or even a different color tank depending on the weather and your personal style.

For jeans, I chose a relaxed-fitting, gray pair that not only keeps the focus on the military cardigan but also allow you to add in fun colored boots (if the jeans were blue, this look would be more Fourth of July-festive rather than day-to-day wearable).

For footwear, I suggest rain boots because they are the most functional option for this weather; however I do understand some people dislike them. If you aren’t a fan of rain boots, Doc Martens are a great alternative – I have found that my lace-up Doc Marten style boots fair pretty well in the rain–and are really stylish for this season!

Because I know my hair becomes a disaster in rain (especially if there is wind involved!), I suggest throwing on a slouchy hat before you go out (I even bobby-pin mine down to ensure it stays on no matter what). This one is cute enough that you could even leave it on once you reach your indoor destination.

This past Sunday, I wrote a column on my favorite kind of umbrella, which I definitely recommend checking out for these types of days. However, for those of you that were not fans of that umbrella or could not find it to purchase, I tried to find some new cute ones that I liked as well. I love the simple geometric pattern on the one above and how well it ties all the colors in the outfit together!

Look Two: It Was a Dark (Cold!) Stormy Night…

Rainy day clothing

Product Information: Tunic: Forever 21, Black Glitter Leggings: Miss Selfridge, Textured Knit Cardigan: Topshop, Women’s Circle Scarf: AE, Boots: Piperlime, Metallic Umbrella: Target

The only thing worse than trekking to daytime classes/work/internships in the rain is attempting to go out at night in the rain!

After all, going out is the number one time us college girls want to look cute and nothing kills that perfect combination of blow-dried hair and impeccable makeup faster than some freezing rain!

Still, I think it is totally possible to make the rain work to your advantage. Here’s what I suggest: go for full out glamour goddess style with a shimmery look that will even shine brighter in the rain!

I am obsessed with the wonderful detailing on this tunic, which looks even better in person (my friend owns it and receives countless compliments every time she wears it). It also has a super flattering fit with that cinched waste and boatneck detail. I also love the metallic flecks in these black leggings, which really highlight the gold accents in the top.

To combat the cold, I love CF reader Alexandra‘s suggestion of wearing tights under leggings to keep your legs cozy!

I also added a knit cardigan and circle scarf on to ensure extra warmth. The scarf is especially great for nights like this when you want to protect your hair but not wear a hat, as you can easily maneuver the shape of it to cover your head.

For shoes, I chose a black faux-leather pair with a sturdy heel–I have a similar pair that have yet to let me down in the rain. However, I don’t recommend wearing them in super slippery weather–when it’s tough to walk outside, always go for flat shoes with a ribbed bottom or risk falling. (I know this from experience!)

Last and certainly not least, I picked an umbrella that would keep you looking golden and glowing. Since this look is all about the contrast of dark and light, I suggest going for golden makeup and big waves or curls (the humidity from the rain should only help this). You’ll end up with a look that is undeniably gorgeous and will bring some much-needed dazzle to a dark and dreary night!

Rainy Day Weapons: Beauty and Hair Products for Rainy Days

Now that you’ve seen my cold, rainy day outfit picks, here’s my list of Rainy Day Weapons. These products will help you fight the seemingly inevitable rainy day frizz and smeared makeup!


Product Information: Waterproof Eye Makeup Remover Pads, Flashy Waterproof Eyeliner Set, Mini Wireless Straightening Iron, Waterproof Shadow/Liner Duo: Sephora, Waterproof Lash Blast Mascara: Target, Hold & Flex Anti-Frizz Spray: Garnier Fructis

  • Makeup: If it’s raining during the day, I suggest going for as little makeup as possible–trust me, you’ll look better with none on than with black smudges dripping all down your face! Of course, I do understand that we all like to put on a little something to look our best, especially when going out at night. Therefore, I suggest investing in waterproof makeup. Most mascaras also come in waterproof forms, so check to see if yours does, too. (If not, I recommend Lash Blast mascara!) Also, go for waterproof liner, either in fun colors like the Sephora set above (great for going out) or in a smoky brown (this Smashbox duo works as waterproof eyeshadow as well).
  • Makeup Remover: While many beauty products may claim to be waterproof, they might not hold up as well as they claim. If you are unsure of the waterproof strength of a product, carry makeup removing pads in your bag to quickly swipe away any rain-induced makeup mishaps.
  • Hair: Definitely, definitely go for some sort of anti-frizz spray or serum on a rainy day! Garnier Fructis has a new line of styling products specifically aimed at battling frizz that I have heard amazing things about. Also, if you are going somewhere and really want to ensure that your look is perfect, there are wireless, miniature flat irons that you can purchase. Charge one up and throw it in your bag so you can tame any frizzies or flyaways in the bathroom once you get out of the rain!

What Do You Think?

Would these looks work for the weather where you live? Do you have any favorite pieces, accessories, or beauty items for dealing with the cold, wind, and rain? What is your go-to bad weather look? Share in the comments!

And if you have any “What Do I Wear There” questions, let me know! Yours may be featured in next week’s article.

Posted on on October 30, 2009 / Filed Under: Fashion Tips / Tags: , , , , , , , ,

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22 Responses to “What Do I Wear There? Outfits for Cold, Rainy Days”

  1. 1
    October 30th, 2009 at 4:33 pm

    This would not work in really cold weather Im an extchange student in northern europe and I basically freaz to death. You need some serious coats girl.

  2. 2
    October 30th, 2009 at 4:33 pm

    It rains about 4567 times a year here in Boston, so I think this post is fantastic! Most BU girls can be seen rocking a pair of rainboots. I’m already on my 4th pair because they keep breaking.

    Hopefully the new pair of hunter boots I scored from Rue La La will last!

  3. 3
    October 30th, 2009 at 5:03 pm

    I love this post, it always rains a lot in my city so thank you for posting this! :)

  4. 4
    October 30th, 2009 at 5:14 pm

    It doesn’t rain too much here, only snows! But the tips are totally spot on.

  5. 5
    October 30th, 2009 at 6:14 pm

    I don’t really like rain boots, so I suggest Aigle of France for boots that fair well in the rain. They are completely waterproof rubber but are crafted to look just like leather riding boots. I’ve got a pair and I love them to death.

  6. 6
    October 30th, 2009 at 6:16 pm

    Also, I forgot to mention that they are now on sale at Martin+Osa:

  7. 7
    October 30th, 2009 at 8:04 pm

    Hi, love your posts!!
    I love the military style cartigan, where is it from?? thanks!

  8. 8
    October 30th, 2009 at 8:25 pm

    I love these kinds of posts but it seems lately it’s almost always been a cardigan and jeans. I realize this is a really versatile outfit but variation would be nice.

  9. 9
    October 30th, 2009 at 10:44 pm

    Wow I love the second outfit! <3

    And I agree with Abbie in comment 8. I already have lots of jeans and cardigans. I want to know what else I need to buy lol. :) But great post!!

  10. 10
    October 30th, 2009 at 11:12 pm

    I love this post, but I am so tired of how no one on this blog links directly to the clothes! It would be nice to own an actual outfit from your sets, instead of having to find ‘inspired looks’ for once! It is impossible to find the clothing in question without a direct link. Grrr, frustration. Isn’t Polyvore for that?

  11. 11
    October 30th, 2009 at 11:32 pm

    hmm. i really like that cardigan in the first outfit but when i went to the website it wasnt there.. Maybe someone knows where it really is from??? cause i really love it to death

  12. 12
    October 30th, 2009 at 11:47 pm

    The first outfit is perfect for rainy days, and I’d suggest on those biting icy/rainy days wear leggings underneath those jeans! And for really cooldd areas, you’ll need some thick coats, not wool or trench ones. On those horrible RAIN days where you can’t get away with an umbrella, what I do, and a lot of other people is wear my ski jacket, mine can unzip so I can also wear it on top of a coat if I want to. It protects me and blocks wind.

  13. 13
    October 31st, 2009 at 6:48 am

    Great post! I also wrote about winter must-have on my blog and I see we agree on several points!

    Milana from

  14. 14
    October 31st, 2009 at 12:11 pm

    A lot of the times on Polyvore, the clothing is from past seasons or is sold out. While I agree that it would be more helpful if they could direct link to the clothing item itself, oftentimes that is impossible.

  15. 15
    November 2nd, 2009 at 4:28 am

    I’m studying in Paris for the semester and although it doesn’t snow in the winter months (a nice change for me, being from the Midwest) it most certainly rains AND gets cold.

    The two outfit ideas are very cute and doable for those kind of days and THANK YOU for suggesting make-up and hair solutions. My hair doesn’t poof in the rain but it does fall limp and refuse to hold a curl. Usually I just comb it and hope for the best because my hair is too short for a pony-tail right now.

  16. 16
    November 2nd, 2009 at 12:32 pm

    i agree with the first post. i go to college in the mountains. cardigans and trench coats are not practical!

  17. 17
    November 2nd, 2009 at 2:44 pm

    Hey guys! Hope you all had a great Halloween weekend.

    Lisa and Aleyson: I completely understand your viewpoints that the above coats would leave you freezing. As I have mentioned in previous posts and quickly passed over in this one, I really feel like coats are a personal choice so I do not want to give absolute suggestions on them since they have different requirements due to your lifestyle and climate! Therefore, i just try to give good base outfits that people in a variety of colder weather climates can wear since CF readers are really from all over. The last post on this site was for more summer/spring weather rain showers, so I was just trying to update for cold(er) weather. Sorry for any confusion–I should have addressed this all in the article!

    Anon: Thanks for the tip and the link, those are adorable!!

    As for the linking situation, we do use Polyvore on this site to find products for outfits and as Ashlee pointed out, sometimes the clothing on Polyvore can no longer be found on the websites. I’m so sorry about this, I try to avoid putting up clothes that can’t be found! The cardigan in the first outfit is from TopShop and I know they have it in their New York store; however I realize it is not an option for all of us to get there. I have seen similar ones at Forever 21 though (for much cheaper!) so maybe check out there!

    Thanks as always everyone, you have some great tips in here!

  18. 18
    November 2nd, 2009 at 2:46 pm

    Oh and super quick:

    Abbie and Vivi, I try to add cardigans on to a lot of my outfits so that they will work for people in climates that are warmer (since they can just look at the outfit sans cardigan) and for people who live in colder areas, but I will definitely take this into consideration and try to change things up!

  19. 19
    April 14th, 2011 at 6:39 pm

    i would wear shorts because thats what i would make my kid do

  20. 20
    September 5th, 2012 at 7:25 pm

    where can I buy a good mini wireless straightener at a decent price?

  21. 21
    July 29th, 2014 at 1:01 am

    Awesome post! Although wish there were a few more outfits!

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