Windy, wet, cold weather is nobody’s favorite. It makes us feel uncomfortable and it can be even depressing. This guide addresses how to stay in thermal comfort and in style. It provides tips to maintain great style even in painfully cold weather and breaks “how to achieve the look” down in easy-to-follow steps using different example outfits. Read about the best cold wet weather outfits on windy days to create thermally comfortable, but stylish winter looks.
Updated: 11/21/2021
-
-
- Avoid to Enhance the Misery of Windy, Wet Weather with Your Clothes
- How to Stay Warm in Style
- Why You Shouldn’t Wear a Down Coat on a Wet, Rainy Day
- A Reason Why You Should Add a Pop of Color
- Best Outfit Ideas for Cold, Wet Winter Days
- How to Layer When the Arctic Vortex Brings Cold Air
- Outfit for Temperatures Around Freezing Broken Down in Layers
- Stylish Layered Outfit for -20F Broken Down
- Business Casual Layering Broken Down in Photos
- Style Layering Secrets for Cold Weather
- Best Layering Outfit Ideas for Cold Weather
- Wrapping Up the Best Cold Wet Weather Outfits
- References
-
Disclosure: There are affiliate links in this post.
Avoid to Enhance the Misery of Windy, Wet Weather with Your Clothes
Gray and black winter clothes enhance the miserable feeling of gray, wet winter days. The wind blows the rain or snowflakes into your face. The wet and cold creeps everywhere. As if the gray skies, gray streets, and nasty wind weren’t enough everyone at the tram station is dressed as if they are coming just out of the coal mines. Gray and black everywhere, the umbrellas, coats, anoraks, scarves, gloves, bags, shoes, boots, …, you name it. A typical winter day somewhere in mid-latitudes – it takes down everybody’s mood. Everyone looks dull, annoyed and miserable. You wonder whether it is a new contagious virus. How to up your and other people’s mood? What to do about windy, wet weather dressing wise?

You can't change the weather, but you can change your mood. #mood #wx Click To Tweet
But you successfully can change how you dress. Feeling comfortable in your clothes can up your mood, and make the day less miserable. Here are some tricks to do so.
How to Stay Warm in Style
The closer the weave of a fabric is, the better it protects you from wind. My favorite fabric to keep the wind out is leather. It does not matter whether it is the outer layer or just a leather blazer, bomber or motorcycle jacket under your outerwear.
It is also important to understand that wind chills. Thus, even though it may be just around freezing (you hear the Alaskan talking here), the air feels much colder, the stronger the wind blows. Take this in mind when dressing!
A thin air layer is a great insulator*. Therefore, layer. For instance, a layering top under a sweater/jacket under your coat, tights under your lined pants or jeans. Boots are better than booties, longer coats better than short coats. If you hate the heavy weight of a long coat on your shoulders, go for a short coat plus insulating over-skirt (see example below). For tips how to layer posh casual on cool or windy days see the post at the link.

Why You Shouldn’t Wear a Down Coat on a Wet, Rainy Day
Unless your feather puffer coat has a water repellent outer layer, it is not a good idea in wet weather. Recall the cold feather-beds when you slept in granny’s attic during your childhood! The feathers take up humidity. The water evaporates due to your body heat and the evaporative cooling makes you feel cold. Thus, in general, go for fabric that lets moisture go just one way – from your body to the ambient air, but not vice versa. You can find what to look for in a down coat in this post.
A Reason Why You Should Add a Pop of Color
Wearing bold colors makes you feel like a gold fish in a sea of herring and make you feel good. You can achieve the same effect by creating an interesting outfit with different structures. The secret behind this kind of outfit is that when everything seems to look the same. Thus, the humans’ eyes get bored and search for something different. In the moment, the eyes fall on your outfit there is an unconscious glimpse of success in the onlookers’ eyes. It makes them and you feel better than before at least for a moment.
Add a pop of color to your outfit to brighten up a cold, wet gray day. #feelinggood Click To TweetMission accomplished!
Best Outfit Ideas for Cold, Wet Winter Days
Try these outfits on wet, cold winter days:
- Long-sleeved T-shirt/layering top under flannel shirt, cardigan, winter coat with long leather gloves, leggings under lined leather pants, soft, but tightly woven scarf, wind-secure hat (e.g. beret, beanie, pompom hat), socks and booties
- Skinny J Brand jeans with Dior over-the-knee booties, long-sleeve T-shirt under cable-knit sweater and a long coat with scarf and hat
- Two pair of tights, skirt, boots turtleneck sweater under blazer under a long coat with gloves and hat




Stylist’s tip: Style your outerwear like an outfit under consideration what shows from your “indoor outfit”.
How to Layer When the Arctic Vortex Brings Cold Air
Clothing reduces energy loss, i.e. loss of your body heat. Thin air layers are best for protection from cold ambient air because a thin air layer is a bad conductor. In other words, it is a great insulator. You know conduction from your iron pan. Despite the handle isn’t in contact with the stove the iron handle gets hot. This happens because the molecules conduct the heat. Some pans have a wooden handle as the wood is a bad conductor and hence insulated your hands from the heat. Similarly you use a sheep skin or thin wool felt insole to avoid cold feet at frigid temperatures. What you basically do is to reduce the loss of your body heat to the cold ground.
Let’ s get back to insulation in dressing. In addition to looking stylish, layering creates appropriate insulation when it is painfully cold outside. For both style and best insulation how to layer is key. Wherever the fabric is in direct contact with your body and/or the environment, conduction takes place, and you will feel cold in no time. This means tight layers won’t do the trick. Also wrong layering may break the style or may draw attention to your not so favorite parts of your body. Not to mention that you may end up looking like the Michelin man.
When layering clothes, avoid to look like a dumpling. #styleadvice #layeringguide Click To TweetDid you know that we loose roughly 10% of our body heat from our head? The head makes up about 7% of our body surface. The heat loss is because the exposure of skin and hair to the elements. Therefore, wearing a head is a Must to not feel cold so fast. In Interior Alaska, many inhabitants wear face masks at 40 below, while others think that 40 below is great for a bikini look.

Outfit for Temperatures Around Freezing Broken Down in Layers
The outfit below is for a day with temperatures just below the freezing point. For someone living in Alaska, these conditions are still considered “warm” (as compared to -20F, -28.9oC). Thus, I am wearing my denim coat and booties with insole, one pair of tights, a knit skirt, cable knit sweater and a belt. Not seen is my underwear consisting of a slip, bra, panty and short sleeve Tee.
However, for those of you who live down south in California or in states along the Gulf of Mexico, around freezing temperatures are very cold. Thus, double up on the tights and go for long sleeve underwear. Outside add a scarf and hat. A beret looks stylish with a denim coat. A pom pom hat would be great too when you want a more casual look. Read more on creating ageless style with trendy hats.



Stylish Layered Outfit for -20F Broken Down
The photos below show me in front of a huge snow pile in the parking lot at work. I am wearing tall boots with insole, a shearling coat that I belted for shape, and a beret. Underneath is my work outfit of cashmere sweater, pleated plaid wool skirt. The scraf is for style and to cover the neck. Below this look there are two pair of tights, a long sleeve silk top and panty as underwear and a bra (not shown). Furthermore, I wear a long half-slip under the skirt as the skirt has no lining (also not shown).




Business Casual Layering Broken Down in Photos
The photos below break down what I wore over my underwear and shape wear to stay comfortable and warm on a cold winter day on the commute, when running from building to building, and sitting at my desk. These photos provide an idea about how to layer. They illustrate that when taking off a layer the remaining look should still look like a stylish outfit that speaks for itself.
How to layer: A layering outfit should still be great when a layer is taken off. Click To Tweet



Put on gloves, scarf, and a hat in addition to your coat for a styled winter outfit. More on tips to style your outerwear.


Style Layering Secrets for Cold Weather
Here are some of my secrets to maintain stylish in painful cold weather.
- Wear silk or polypropylene long underwear under your pants and sweater/shirt.
- Depending on where you have to go wear slim, straight – read not skinny – winter wool trousers with lining or Alaska weight jeans with flannel lining.
- Layer with a slim qiviut or wool sweater and a polar fleece vest for insulation. Note that qiviut is the underwool from the Arctic musk ox and provides the best insulation while looking chic and thin.
- When layering pieces (sweater/cardigan, sweater/vest) of different color make sure it is either short over long or long over short with a difference in hem length of at least 2 inch (5 cm) and up to 5 inch (12.5 cm) except for a long vest or long cardigan that hit just above or below the knee.
- Wear a turtleneck sweater to keep your neck insulated. They look stylish. Accessorize with a brooch on the side of the turtleneck or pearls when you style a winter work outfit for a conservative work environment.
- Alternatively, a crewneck or mockneck sweater with a silk scarf work fine (see the photo of the LOTD below).
- You may consider to wear a (turtleneck) sweater with a matching cardigan as a modern version of the evergreen twinset classic. It looks beautiful with layers of pearl necklaces à la Coco Chanel.
- When your work dress code calls for skirts/dresses wear two pair of tights, long sleeve underwear, a silk or polypropylene half slip or slip with skirts and dresses, respectively. The right underwear are your base layers for cold weather.
- Wear two pair of wool socks for extra insulation in winter boots a size larger than your summer shoes.
- Squeezing your feet in winter boots is a recipe for cold feet. Click To Tweet
- A hat, scarf, and gloves are must-haves in the cold. #polarVortex Click To Tweet
- Gloves are not only a great accessory to keep your hands and fingers insulated, but also finish the styling of any winter outwear when chosen to match the vibe of the look. See 13 tips how to improve your style with gloves at this link.
- Wear gloves with adjustable wrist band or knit cuffs to avoid that cold air enters and mixes with the air between your layers. They also exist as elegant leather gloves, for instance, at LeatherCoatsEtc.
- Wear outerwear that has knit cuffs in the sleeves for the same reason. Wear outerwear with knit cuffs to keep frigid air out when the polar vortex goes thru town. #polarVortex Click To Tweet
- When your boots have a wide opening at below the knee or at the calf, wear boot toppers to hinder cold air to get into your boots from the top and as a stylish element of your outerwear outfit. Yes, mature women can look great with boot toppers.
- Go for a chic Russian wool scarf, a silk scarf or a knitted qivuit scarf to insulate your neck when your outerwear look must be dressy and work appropriate. Even if not, style your outerwear, it’s an outfit too. And the fun with styling keeps your mood up.
- Don't forget to style your outerwear. Click To Tweet
- Wear a hat that covers your head, and ears. Shearling hats, and berets are great trendy options.
- When you expect to stay outside for a long time like walking the dog or waiting for public transportation wear insulating pants over your trousers or an insulating skirt over your skirt/dress for extra insulation.
- When dressing for the commute to work wear a tailored down-coat with water-resistant outer coating. Alternatively, go for a tailored below-the-knee length shearling coat. You can find what to look for in a down coat at the link.
- In windy cold weather, your outermost layer must protect against wind too. Leather coats with quilted lining are a great option.
Best Layering Outfit Ideas for Cold Weather
Here some work outfit layering ideas to stay warm and look stylish.



Tip: Under wider or straight dress pants you can wear long-Johns or leggings or even tights. Put the long-Johns or leggings into your socks (knee-high are best) so you can avoid a cold gap. Also make sure the resulting bulk (or long underwear) doesn’t show when you sit or sit crossing your legs.
Long underwear showing under your trousers is never in style. #winterhassle Click To Tweet


Wrapping Up the Best Cold Wet Weather Outfits
Wind goes thru all gaps in your outfit. Wet weather like wind has a chill factor when temperatures are around the freezing point. Leather is great to keep the wind away. However, it needs layering underneath to stay warm. Windy wet, cold weather often occurs on the west side of mid-latitude continents. Examples are western Europe, British Columbia, Washington State and even Southeast Alaska, i.e. the Pacific Northwest. You can find a post devoted to the secrets of stylish dressing for Pacific Northwest weather around the seasons at the link.
When you like the style advice and tips in this post, you want for tips for all kind of dressing situations you may want to buy my book How to Dress for Success in Midlife.
Do you style your outerwear like an outfit of its own? What are your fashion and style challenges on cold, wet days? Let me know, I am curious how I can help you.
References
Mölders, N., 2019: Outdoor Universal Thermal Comfort Index Climatology for Alaska. Atmospheric and Climate Sciences, 9, 558-582. doi: 10.4236/acs.2019.94036.
Shulski, M. and Wendler, G. 2007: The Climate of Alaska. University of Alaska Press, Fairbanks. 216 p.
Photos: G. Kramm
© 2013-2021 Nicole Mölders | All rights reserved