How To Dress Warm And Stylish In Winter

Nobody likes being cold and uncomfortable in winter, but throwing on a random selection of your thickest winter layers will not only not be the warmest thing that you can put on, but it will feel and look bulky - an entirely different kind of uncomfortable, and not that cute of a look.

Dressing warmly for winter weather does not have to mean compromising on style. Here are my Top 5 tips for dressing warm and cute in cold weather.

Tip #1: Choose Your Base Layers Carefully

When dressing for warmth, the layer that is closest to your body is the most important one. It should serve two main purposes:

  • Retaining the heat that your body naturally produces;

  • Repelling the moisture (a.k.a. sweat) that your body naturally produces, keeping you dry.

Selecting the right material for a base layer that can perform these two functions is key. You will get the best results by wearing something that fits close to your body, ideally in a natural material like wool (like the one pictured below), or silk. If natural materials are not in your budget there are fantastic synthetic options on the market that will keep you just as warm, but keep in mind that synthetics are not great at repelling odors, so they may need to be washed more often.

These wool leggings are an excellent option for warmth at an affordable price. $49.99 on Amazon*.

Make sure your torso, legs, and feet are covered by a solid base layer underneath your clothes. This alone will make a huge difference in keeping you warm.

Tip #2: Consider The Materials Your Clothes Are Made Of

When it comes to dressing warm, the materials that your clothes are made of matter more than the number of layers you are wearing (which is great news if you are trying to avoid the Michelin look). This is particularly important when it comes to your coat, or your outermost layer. It is critical that your outer layer is made of a material that at the very least is water repellent, if not completely waterproof. This ensures that even if your outer layer gets wet (due to rain or snow), your clothes beneath it, and therefore your body, will remain dry and warm.

Belted coats are great for enhancing your silhouette in winter. This one from Calvin Klein is 80% wool. $148.89 on Amazon*.

Some materials, like cotton, acrylic and certain polyesters, are terrible at retaining warmth when they get wet. It is better to pick something like wool, at least 80% wool in order to keep you really warm. Make sure that your coat fits you properly, especially at the shoulders. Clothes that fit you better will always look more put together than clothes that are the wrong size. 

Tip #3: Pay Special Attention To The Shoes You Choose to Wear

When it comes to stylish shoes, anything with a pointy toe will instantly make the visual line of your outfit appear longer, since they continue to draw the eye down past your feet. Shoes are an outer layer as well, so the materials that they are made of will determine how well they can keep your feet warm, particularly at the sole. The thicker the sole of the shoe, the more distance there is between your body and the cold wet ground. A textured rubber sole that is at least ¼ in (about 0.5cm) will be great at keeping your feet warm and preventing you from slipping on ice.

Shoes that are waterproof are always best since they keep your feet dry, and bonus points if you can find something that is fleece or wool lined - that will keep your feet really warm!

This is my favorite pair of waterproof shoes for winter. Highly recommend! *

This is my favorite pair of waterproof shoes for winter. Highly recommend! *

Tip #4: Balance The Proportions Of Your Outfit

Depending on what you have available to wear, you may end up with a more voluminous top (like a oversize sweater), or a wider bottom. To make the outfit look sleek, balance the proportions of the outfit by pairing bulky tops with tailored bottoms, and vice versa. When wearing bottoms with more volume, pair with a top that fits close to your torso.

This is a great tip regardless of whether you are dressing for winter or not; the eye overall likes balance. Bulking all around is what creates the frumpy winter look.

This outfit from my 2020 Winter Capsule Wardrobe is still one of my favorites.

This outfit from my 2020 Winter Capsule Wardrobe is still one of my favorites.

Tip #5: Stick To A Neutral Color Palette and Minimal Pattern For Your Accessories

I wholeheartedly believe this: your accessories can make or break your outfit. When it comes to winter accessories, which are necessary for your warmth and comfort, a cohesive look will prevent them from clashing against anything else you wear with them.

The easiest and simplest way to do this is to match your hat, gloves, and winter hat to each other, and then match those to your winter coat. This doesn’t mean that all of them have to be of the same color, but a cohesive color palette will tie the look together.

Source: Getty Images

Source: Getty Images

A great example of all of these tips being put into practice was Michelle Obama’s outfit for the Inauguration of Joe Biden. She was wearing a wool turtleneck sweater that fit close to her torso, paired with flare leg trousers to balance the proportions of the outfit. Her top layer was a long wool coat, and she kept her accessories and pointy toe boots in a neutral color that matched the coat. I’m pretty sure that underneath it all, she was wearing a good base layer and wool socks, but we will have to ask her stylist that some day.

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