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 in style. In easy-to-follow steps, it breaks down “how to achieve the look” by using different example outfits. Read about the best cold wet weather outfits on windy days to create thermally comfortable, but stylish winter looks.



Disclosure: There are affiliate links in this post.


How to Avoid to Enhance the Misery of Windy, Wet Weather with Your Clothes

A typical gray, rainy, and windy winter day takes down everybody’s mood. Not only the sky, streets, and buildings look gray, but also most people wear gray or black. Consequently, everyone looks dull, annoyed and miserable like they caught a new contagious virus.


Wear Color on a Gray, Wet Day

Wearing bold colors makes you feel like a gold fish in a sea of herring and make you feel good. More on the psychology of upping the mood in rain by wearing color.



Why You Shouldn’t Wear a Down Coat on a Cold, Wet, Rainy Day

Unless your feather puffer coat has a water repellent outer layer, do not wear a down coat in wet weather. Recall the cold feather-beds when you slept in granny’s attic during your childhood! Feathers take up humidity. Due to your body heat the water evaporates. The related evaporative cooling makes you feel cold. More on what to look for in a down coat.

Instead, wear a coat made of water-repellent fabric like loden or molton. The authentic pea-coat was created for wet, humid weather. Another garment made with for cold, humid, windy weather in mind is the original duffel coat.



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.


How to Stay Warm in Style

The closer the weave of a fabric is, the better it protects you from wind. Leather is great to keep the wind out.

When dressing take in mind that wind chills. Therefore, even though it may be just around freezing, the air feels much colder, the stronger the wind blows.

A thin air layer is a great insulator*. Therefore, layer a top under a sweater/jacket under your coat, tights under your lined pants or jeans. Boots are better than booties, long coats are better than short coats. To avoid the heavy weight of a long coat try a short coat plus insulating over-skirt (see example below). More on layering for thermal comfort.


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



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, tightly woven scarf, wind-secure hat (e.g. beret, beanie, pompom hat), socks and booties.
  • Skinny jeans, over-the-knee booties, long-sleeve T-shirt under cable-knit sweater and a long coat with scarf and hat.
  • Two pairs 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


Tip: Style your outerwear like an outfit under consideration of what shows from your “indoor outfit”.


Be aware 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.

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



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.



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



Avoid to Get Cold Feet


  • Water-proof shoes with a thick sole or add a sheep skin or thin wool felt insole.
  • Two pair of wool socks for extra insulation.
  • winter boots a size larger than your summer shoes to not squeeze your feet when doubling socks or adding insoles.

More on avoiding cold feet.


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 office look.



Cover Your Head

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.

In windy, cold weather, wear a hat that covers your head, and ears. Shearling hats, and berets are great trendy options.


Style Layering Secrets for Thermal Comfort in Cold, Humid Weather

Here are my secrets to maintain stylish in painfully cold weather.

  • Wear silk or polypropylene long underwear under your pants and sweater/shirt.
  • Depending on where you have to go wear slim, straight 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. Qiviut is the underwool from the Arctic musk ox.
  • 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. More on stylish layering for winter.
  • Wear a turtleneck sweater. Accessorize with a brooch on the side of the turtleneck or pearls for a winter work outfit in a conservative field.
  • Alternatively, a crewneck or mock-neck sweater with a silk scarf work fine (see outfit inspirations).
  • Try a (turtleneck) sweater with a matching cardigan as a modern version of the evergreen twinset classic. Add layers of pearl necklaces like Coco Chanel.
  • When wearing skirts/dresses use two pairs of tights, long sleeve underwear, a silk or polypropylene half slip or slip with skirts and dresses, respectively.
  • Wear gloves with adjustable wrist band or knit cuffs to avoid cold gaps. Gloves finish the styling of any winter outwear when chosen to match the vibe of the look. More on styling glovesthat cold air enters and mixes with the air between your layers.
  • Wear outerwear that has knit cuffs in the sleeves for the same reason.
  • When your boots have a wide opening at below the knee or at the calf, wear boot toppers to close the cold gap. More on mature looks with boot toppers.
  • Go for a chic Russian wool scarf, a silk scarf or a knitted qiviut scarf to insulate your neck for a dressy, comfortable work appropriate look.
  • When you expect to stay outside for a long time wear insulating pants over your trousers or an insulating skirt over your skirt/dress for extra insulation.
  • In windy, cold weather, your outermost layer must protect against wind too. Leather coats with quilted lining are a great option.


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).
However, for those of you who live down south, around freezing temperatures are very cold. Therefore, 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 pompom hat would be great too when you want a more casual look. More on 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

In the photos below, 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 scarf is for style and to cover the neck. Furthermore, I am wearing two pairs of tights, a long sleeve silk top, briefs and bra as underwear, and a long half-slip under the skirt.


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


midlife blogger looking posh and stylish in a cold weather office outfit
GNW cashmere wool sweater, silk scarf to keep the neck warm, Pendleton plaid pleated wool skirt (slip and tights are not visible), Gucci belt, L.K. Bennett boots, Hermes collier de chien bangle and leather cuff, LeatherCoatsEtc 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 for thermal comfort in style. These photos illustrate that when taking off a layer the remaining look should still look like a stylish outfit that speaks for itself.


Tip: Layered outfits should still be great when a layer is taken off.


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 & 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.



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



Wrapping Up the Best Cold Wet Weather Outfits

Wind goes thru all gaps in your outfit. Like wind, wet, humid air chills 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. More on stylish dressing for Pacific Northwest weather.


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

© 2013-2023 Nicole Mölders | All rights reserved