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Stylish Winter Dressing

Updated on January 10, 2017
So how can we change it?
So how can we change it? | Source

The Key to Winter: Layers, Layers, Layers!

When temperatures drop, sometimes it seems like we can't put on enough clothing! The wind whips through our coats, leaving us to survive in what my mother always called "Naked Weather" (doesn't matter what you are wearing, as the wind will make you feel naked!).

Thanks to a little bit of wardrobe planning, we can combat this drop in temperature without having a decrease in style. By utilizing layers, thick and thin, we can create stylish, comfortable, chic outfits for any low temperature, regardless of the occasion.

No more overstuffed marshmallows for us!

Casual Layers in Winter

The easiest style issue to address for winter is casual dressing. Assuming that you will either be at home, with friends, at school, or running errands, casual winter clothes should be comfortable, but that doesn't mean you can't look great too. For those who work in a casual office or environment, you should be able to take this as a basic guide and use accessories and shoes to better fit your dress code.

Some of my favorite off-day items for winter start with warm, protective base layers. A lightweight thermal shirt (I am not a huge fan of waffle-weave) is silky against the skin without adding bulk. With a large variety of companies and materials to choose from, there is an option for everyone. My personal favorites are organic cotton or bamboo, as they can help to whisk away moisture from the body without bulk or smell.

Throw on a pair of fleece lined leggings in your favorite color or pattern, and we have our base layer complete. In truth, any leggings will do, but look for thicker materials in the winter. Cable-knit sweater leggings, fleece, and even wool, can be great cold weather options. Cotton fleece leggings are my new favorite thing for work, as they look sleek, but help me temperature regulate much better in a heated environment.

Casual Layers

A simple, yet chic, casual winter look.
A simple, yet chic, casual winter look. | Source

But we aren't done yet! Top your undershirt with a comfortable sweater. I like an oversized style, as it allows for movement and modesty. Pullovers typically work better in this layering, as we have more layers still to add. If you are staying in, feel free to wear just a cardigan over your undershirt.

If you are brave enough to spend your casual day out and about, throw on a fleece vest. A vest provides warmth to your core, keeping you toasty, but reduces overall bulk to keep you from feeling overstuffed. For school, errands, or chores, having a larger range of movement can make life much more bearable during the winter months.

A slouchy beanie adds style and warmth, and simple jewelry helps you look pulled together. Just because it is winter does not mean you should sacrifice your personal style. Accessories are a great way to keep from feeling like a semi-hibernating being.

For shoes, I will admit that function beats form. A sheepskin lined boot is my favorite for casual winter dressing, as it is warm and comfortable, and still surprisingly on trend. I imagine that eventually the chunky winter boot will fall from style favor, but for now, it is a ubiquitous accessory that fits our weather bill. A lace-up duck boot can also be a great option in slushier weather, and more and more cute styles appear each year. Make sure to wear good, thick socks if rocking a non-lined style!

Winter Work Wear

Attempting a professional, streamlined look in inclimate weather can be a true challenge. The daily commute can become windy, rainy, or just downright miserable, and bundling into unattractive layers is a common cop-out.

But by utilizing the same idea of layering techniques that we used for casual wear, we can create a sleek, sophisticated, and warm ensemble, suitable for any office environment.

Professional Layers

Sophisticated office wear for winter time!
Sophisticated office wear for winter time! | Source

More Layers!

Just as with the casual look, we begin with base layers. A pair of thermal long underwear (your choice, and leggings can work as well!) and a silk camisole begin our look, as well as a pair of wool or cashmere trouser socks.

Top the camisole with a sheer blouse, adding layers but reducing bulk through thinner materials. A pair of tweed trousers add additional weight while still keeping the look very clean. You could alternatively do a thick pair of tights and a skirt in place of pants.

Add a cashmere cardigan (great for almost all seasons!), a pair of mid-heel booties, and a whatever jewelry you choose. The cardigan provides breathable warmth, and the booties will give the height wanted for office wear but are sturdy enough to deal with snow and ice. A pair of riding boots could also work well, particularly over slimmer fitting trousers or with a skirt.

Jewelry is a "must" in my book for office dressing. A sleek pair of earrings, a classic watch, and a simple necklace can pull any look into a more professional direction, regardless of season or trends.

Finish the whole look with a wool overcoat, single buttoned and mid-thigh length. This will provide maximum warmth, and unlike a double breasted pea coat, will slim the overall look. I have used a camel coat in my graphic, as this color is timeless and great for all skin tones, but a dark wool (like black or navy) is also great. if you live in a cold climate year-round, it an be worth it to invest in a few coats of different styles and colors. If you wear then often enough, your coats can be a major part of your outfit and style.

A chunky infinity scarf will block any drafts, and a sleek pair of leather gloves adds a warm, in charge attitude to the look. A patterned pashmina is another great scarf option. I like to invest in several every winter to change up my look without having to change coats.

If your office has a varied climate (as many do), this look provides the opportunity to remove and add layers as needed. If you choose a pashmina as your scarf, you can even use it as a shawl in a cooler office.

Staying Warm and Fancy

Possibly the hardest way to dress in winter is for fancy occasions. When wearing a fitted cocktail or evening gown, it can seem impossible to be warm and chic at the same time. However, with some creativity and foresight, we can create a chic, glamorous look that can stand up to the most viciously cold night.

Evening Layers

Timeless winter elegance, no matter the weather.
Timeless winter elegance, no matter the weather. | Source

Fancy Layers

Base layers are key to warmth, yet again. But, for a night out, long underwear just is not appropriate or sexy. We can counter this by wearing a pair of opaque, thermal tights. Thick tights keep gams from appearing pale and cold in winter drafts, without sacrificing style..I am an enormous fan of opaque in winter, as it adds some sexy mystery while still keeping legs from freezing.

Instead of our usual thermal shirt, I recommend a shapewear tank. While it will provide a sleek silhouette for most figures, the density and fit of the garment creates a nice, warm base layer. Just make sure to find one with thin straps and a low neck/back to fit beneath your dress.

The next layer is the easiest: your dress. I have chosen a fitted black sheath for my example, as it is a flattering shape and everyone needs an LBD. With the tights, it creates a long, lean line that just oozes sophistication and allure. A sparkly sweater keeps arms warm, while glimmering accessories up the drama.

A sleek pair of black wedges (much more stable than stilettos in bad weather), a full skirted coat (although a sleeker, work-style one is also fine), and fur muffler complete our look. You could also choose a pair of heeled boots, as long as they are not too chunky in design.

The finished outfit is sleek, sparkly, and as warm as we can hope!

Cold Weather Reminders

When dressing for winter, remember:

  • Thin layers are the best, regardless of occasion
  • Consider if footwear choices are appropriate but still stylish.
  • Invest in a sleek wool or cashmere coat for years of sleek winter wear
  • Changing up scarves and gloves can greatly change a look
  • Don't forget your accessories
  • Just because it is cold doesn't mean you can't look good!



Now you can tackle those snowy streets in style!
Now you can tackle those snowy streets in style!

What is your favorite layer?

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