You are currently viewing What You Should Wear in Cold, Wet Weather

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


      1. Avoid to Enhance the Misery of Windy, Wet Weather with Your Clothes
      2. How to Stay Warm in Style
      3. Why You Shouldn’t Wear a Down Coat on a Wet, Rainy Day
      4. A Reason Why You Should Add a Pop of Color
      5. Best Outfit Ideas for Cold, Wet Winter Days
      6. 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
      7. Style Layering Secrets for Cold Weather
      8. Best Layering Outfit Ideas for Cold Weather
    1. Wrapping Up the Best Cold Wet Weather Outfits
    2. References


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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?


fashion blogger in cold windy day look with motorcycle jacket over turtleneck sweater
Lookbook Store leather jacket (old; similar here), Anne Klein turtleneck sweater, London jean bfs, pearls, Kieselstein Cord belt. This “indoor” outfit with pop of color is stylish and keeps you warm on a gray windy cold winter day.


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.


style book author in thermo skirt over leather pants to stay warm in windy cold wet weather
Newport News leather pants, Skhoop thermal skirt, jacket, Hunter boots, and LeatherCoatsEtc beret. A perfect look on a cold windy winter day



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.

Mission accomplished!

Add a pop of color to your outfit to brighten up a cold, wet gray day. #feelinggood Click To Tweet



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


midlife blogger showing how to wear pink over 40
Side view of windy cold day look


 jewelry peacock silver pendant
Details of necklace


stylist showing how to wear pink over 40 in winter at the office
Outfit details: Brown unbranded waterfall cashmere cardigan, Lands End mock-neck cashmere sweater, I.N.C. chocolate brown leather pants, brown Clark booties, Festina watch, Hermes H bangle, and peacock necklace


fashion blogger in winter look with beret to protect from wind and wet weather
Diamond leopard print jacket worn over INC leather pants accessorized with beret, gloves, fuchsia 3.1 Philip Lim bag, and Clark booties worn over the above outfit


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 Tweet

Did 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.


over 50 years old woman in leather sheath dress
Example of how to layer. Leather sheath dress, GNW luxe cashmere sweater, GNW tights, Festina sports watch, Hermes collier de chien bangle, statement pendant necklace, and DKNY button-down shirt Steve Madden Mary Janes for a classic with a twist winter office 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.


over 50 years old blogger in denim coat layered over knit wear to stay warm in cold weather
Front view of outerwear


mature woman in cold weather office outfit in black knits and tights with belt
Front view “indoor layer”


style book author in all black winter clothes with colorful statement belt
Outfit details: Max Mara denim coat, Harley Davidson booties, unbranded structured bag, Hermes collier de chien bangle, Vince knit skirt, Anne Klein crewneck cashmere sweater, Rebecca Collins belt, LeatherCoatsEtc gloves (all own) and tights c/o Histik Legwear



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).


Alaskan fashion blogger standing in the cold in a shearling coat with stylish accessories
Side view outerwear


style blogger looking stylish in a cold weather office look with skirt
Front view “indoor” outfit


mature woman looking stylish in shearling coat, beret, gloves on a cold winter day
Front view outerwear


mildife blogger looking posh and stylish in a cold weather office outfit
Outfit details: GNW cashmere wool sweater (dyed blue), silk scarf to keep the neck warm, Pendleton plaid pleated wool skirt (slip and tights are not visible), Gucci belt, L.K. Bennett tall sude boots, Hermes collier de chien bangle and leather cuff, LeatherCoatsEtc wool beret, GNW Luxe sweater, silk scarf, Gucci enamel bamboo buckle belt, Vittoria shearling coat, ethnic belt, unbranded structured bag and blue LeatherCoatsEtc cashmere linen gloves



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


necklace over sweater with accessories
Zoom-in on accessories


stylist in tweet skirt with sweater tall boots necklace
Start with a normal skirt and sweater combination like, for instance, this Eddie Bauer tweed skirt with Anne Klein mock turtleneck cashmere sweater, GNW tights, knee-high boots and long statement necklace. Note that the necklace is already a layer that adds interest and style.


business casual winter outfit with skirt, sweater and motorcycle leather jacket as a next layer
Add a motorcycle leather jacket (Graham and Spencer) instead of a blazer over mock turtleneck sweater, Eddie Bauer tweed skirt with gray opaque tights, heeled knee-high black boots and statement necklace for an edgy, but posh work look


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


woman in winter coat, beret and scarf
Side view outerwear


Alaskan woman in outerwear with gloves, scarf, hat, tights, shearling coat
Winter layering completed with styled outerwear: Cole Haan motorcycle shearling coat, RAK chevron cashmere scarf, leather gloves (similar here), Sanchez tall boots, GNW tights, wool beret and structured bag



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 mock-neck 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.

midlife fashion blogger in layered black, green, tan, white office outfit
Top c/o Covered Perfectly, Isaac Mizahri cardigan, Esprit neckerchief, Kieselstein Cord belt, Gucci Dionyseus buckle, Hermes collier de chien bangle, Banana Republic skirt, and bracelet c/o Lizzy James


style blogger showing an example of the best cold wet weather outfits in down vest and leather skirt
GNW Luxe sweater, down-vest, Kieselstein Cord belt and buckle, Hermes collier de chien bangle, GNW flannel tight, Söfft booties, and neckerchief


over 50 years old woman in casual posh cold wet weather outfit with three horses statement belt
Layering top , Anne Klein cashmere sweater, Pendleton glen check wide pants, GNW socks, unbranded pointy toe pumps, LeatherCoatsEtc beret, Jord bamboo wooden watch, Kieselstein Cord belt and buckle


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


example leather sheath dress as one of the best cold wet weather outfits
Leather sheath (similar here) with silk scarf, Chanel belt, Mary Janes, pantyhose, Hermes collier de chien bangle, Prada bag (all own) and halftee c/o Halftee


pea coat as an example for the best cold wet weather outfits
Leather sheath with Mary Janes, silk scarf, pnatyhose, LeatherCoatsEtc gloves, Prada bag (all own) and pea-coat c/o London Transition



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.




Mölders, N., 2019: Outdoor Universal Thermal Comfort Index Climatology for Alaska. Atmospheric and Climate Sciences9, 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

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