Winter dressing is an art form that balances the need for warmth with a desire for style. But the cold season doesn’t have to mean sacrificing fashion for function. Below, you’ll find our guide to dressing well while staying cozy during the frosty months. Let’s take a look at how to dress in winter.

What is the best way to dress for winter?

Below, you’ll find all of our tips for dressing well during winter. It’s all about layering strategically so you can stay cozy without losing your sense of style.

What is the warmest thing to wear in the winter?

How to dress in winter: all the tips you need to stay stylish and warm | 40plusstyle.com

It isn’t about wearing one thing, but about choosing your layers and materials wisely to keep as much heat in as possible. Jona @the50plusgirl above opts for a cozy coat, and makes sure to keep her head warm too.

Get her look with this similar sweater, jacket, leggings, boots and beanie.

What is the 3-layer rule for winter?

The three-layer rules for winter dressing is a simple and effective method for staying warm and comfortable in cold weather. It involves wearing three distinct layers, each with a specific purpose, to create insulation and protect against the elements.

Base layers are your first defense against the cold. Choose lightweight, breathable pieces to trap heat close to your body, keeping you warm without adding bulk. Look for materials like thermal blends and merino wool.

Then add your middle layer. This is your insulation layer, designed to trap heat. Fleece jackets, wool sweaters, and down vests are good choices.

Finally, your outermost layer should shield you from wind, rain, and snow. A waterproof and windproof coat with insulation is essential if it’s really chilly where you are. Otherwise, you can consider options like a long wool overcoat.

What not to wear during winter?

There are no hard and fast rules. You can wear your summer dress with tights, boots, and a jacket if you want. The key to dressing in winter is not to prioritize style over function. You need both to work together.

how to dress in winter

Let’s look at more tips for winter dressing.

Art of layering

First, layering is super important. Be sure to employ the rule of three as outlined above. You want a base layer, a middle layer, and an outer layer to trap heat and keep you warm. If you’re really cold, you don’t have to stick to three layers. You could add a camisole and a T-shirt under the layers below.

Layers to keep you warm | 40plusstyle.com

Nordstrom Crewneck Side Slit Wool & Cashmere SweaterNordstrom Wool & Cashmere Longline Rib CardiganCole Haan Slick Belted Long Coat

Nicola wears a leopard print coat | 40plusstyle.com

Nicola @40notfrumpy above shows how you can combine style and warmth with her tights and leopard print coat.

Steal her look with this similar sweater, coat, skirt, tights and boots.

Invest in key winter accessories

Accessories are always important for adding the finishing touches to your outfit, but they’re even more essential in colder weather. Keep your hat, neck, hands, and feet warm, and you’ll help keep everyone toasty.

Accessories for winter | 40plusstyle.com

Druthers NYC Merino Wool Ribbed BeanieTreasure & Bond Herringbone Burlap ScarfHelen Kaminski Alma Cashmere GlovesSmartwool Everyday Crew Socks

Choose the right fabrics

Fabric choice is another key consideration. You’re looking for fabrics that insulate, like wool, that can trap warm air close to your body or those that wick moisture away to prevent you from getting sweaty and then cold. Choose fleece, wool, or cashmere. And, when it’s really cold, opt for down or a down substitute.

Sweaters and coats for winter | 40plusstyle.com

AllSaints Lock Roll Neck Asymmetric SweaterCaslon® Brushed Fleece JacketBCBGMAXAZRIA Pillow Collar Hooded Puffer Coat

Boots rather than shoes

Swap out your shoes for boots and wear them with tights, cashmere socks, or leggings. You’re likely to want three different types of boots to see you through the season—a pair of knee-highs, ankle-length booties, and boots that can withstand rain and show. With the prints and colors you choose, you can still let your style personality shine through.

Boots for winter | 40plusstyle.com

SOREL Joan Now™ Chelsea BootsThe North Face ThermoBall Progressive Zip II Waterproof BootiesSteve Madden Dagne Knee High Boot

Colors and prints

You need to be warm, so you need to choose the right materials. But one thing you do have plenty of flexibility over is the colors and patterns you opt for. Choose bold shades and prints to add impact or soft neutrals if you lean towards a minimal style personality.

Colors and prints for winter | 40plusstyle.com

NIKKI LUND Stacey Long Sleeve Midi DressBoden Durham Wool Blend CoatRebecca Minkoff Darren Deerskin Leather Shoulder Bag

Nikki in a red coat | 40plusstyle.com

Nikki @midlifechic above shows how you can make a real impact during the winter months with a bold shade like red.

Recreate her outfit with this similar coat, jeans, booties, handbag and scarf.

For more tips, also take a look at our article on how to wear bright colors for winter and also our article on how to wear red.

Outerwear

Making a careful selection of outerwear is important in colder weather. Your coat will be the first thing anyone notices as you walk in from outside, so choose a style you love. A bright color will get you noticed for all the right reasons. Or opt for a style with faux fur or shearling for a cozy feel. Choosing oversized outerwear will ensure you can fit your knitwear underneath.

Outerwear for winter | 40plusstyle.com

Sam Edelman Notched Lapel Faux Shearling & Faux Suede JacketKaren Millen Textured Wool Blend Short Pea CoatBoden Midi Coat

Choose boots with tred

Stay safe and stylish by ensuring your boots have tred on their soles so you don’t slip during inclement weather. The good news is boots with chunky soles are very much on trend so that you can be practical and chic.

Boots with trend for winter | 40plusstyle.com

Söfft Pecola BootsMarc Fisher LTD Farris Lug Sole BootsKamik Sienna Lo Boots

Add texture

Another thing you can play around with in winter is the texture you choose. You can stay warm, and add interest by choosing rich, tactile materials like velvet, faux fur, shearling, and textured leather.

Check out our capsule wardrobe that mixes textures here.

Wearing textiles for winter | 40plusstyle.com

UGG Fleece Trucker JacketJ.Crew Carolina Velvet PantsMac Duggal Crocodile Leather Buckle Detail Maxi Tote Bag

Eugenia in a teddy style coat | 40plusstyle.com

Eugenia @theeageofgrace above (read her style interview here) opts for a teddy coat and rain boots with chunky soles.

Check out this similar dress, coat, boots, handbag and sunglasses.

Don’t forget to also take a look at our article on how to mix textures in your outfit.

Do you have more tips for dressing in a way that keeps you both warm and stylish in winter? Let us know in the comments below.

Continue reading:

  1. How to layer for winter without looking bulky
  2. Neutral outfits to wear in winter and fall
  3. How to wear bright colors for winter

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How to dress in winter: all the tips you need to stay stylish and warm | 40plusstyle.com

Feature image by Jona @the50plusgirl

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