Winter can be one of the most challenging seasons to consistently wear winter outfits for women that are both weather appropriate and figure flattering.

When the primary motivation is keeping warm while facing dreary days, the temptation is there to simply throw on as many pieces as possible and get out the door. But, putting together chic winter looks doesn’t have to be a challenge.

Simple planning can actually keep you both warm and stylish through the winter months without having to sacrifice function or aesthetically pleasing looks.

In today’s post, I go over 11 easy tips that can turn around a less-than inspiring-wardrobe into one that excites you about getting out of your warm bed and braving cooler temperatures.

11 ways to stay chic with the best winter outfits for women this winter

1. Start with the basics – thermals

It may sound obvious, but when thinking about the best winter outfits for women, if you opt for a thin thermal layer underneath your outfit, you can then often get away with wearing what you usually would without worrying about being cold.

Below are some more thin thermal tops you could wear. Also check out the best thermal underwear to wear under everything when the temperature dips.

Uniqlo HEATTECH long sleeve shirt | 40plusstyle.com

Uniqlo HEATTECH long sleeve shirt

Thermajane fleece lined thermal set | 40plusstyle.com

Thermajane fleece lined thermal set

2. Layer, layer, layer for winter style points

How to look fashionable in winter - a layered knitwear look | 40plusstyle.com

Style tip: Purposeful layering is the perfect way to achieve warmth while putting together a chic look.

Layering allows you to play with a mixture of patterns or textures, while being functional enough to support all the varying temperatures you encounter on a winter day (from frigid cold outside to overheated offices and cars).

The key is to get thinner pieces that offer maximum warmth (such as cashmere), layer on scarves to pull the looks together, and play with varying lengths to flatter your body shape

Sandra @lapecosapreciosa above shows how you can layer a sweater vest over a turtleneck sweater. She shows off her waistline and makes her legs look longer by cinching with a belt.

Get her look with this similar sweater, vest, jeans, booties, belt and fedora.

Another winter outfit for women featuring layering

An easy way to layer is to wear a poncho or wrap over your sweater.

Winter layering ideas for winter outfits for women | 40plusstyle.com

PULI cross front ponchoHerou turtleneck layering topSTS Blue skinny jeansKate Spade New York huggie earringsALYSSA hobo shoulder bagBlondo waterproof boot

Or, you can play around with the length of your layers and wear a shorter jacket over a longer top.

Winter layering ideas for winter outfits for women | 40plusstyle.com

Decrum lambskin leather jacketCaslon turtleneck sweaterBP. high rise leggingsDr. Scholl’s ankle bootStreet Level slouchy shoulder bagPendleton oversized wool scarf

3. Go over the knee to create stylish winter outfits

Stylish over the knee boots for winter outfits for women | 40plusstyle.com

Style tip: Many women (especially those over 40) shy away from over the knee boots.

And this is definitely the perfect strategy if you happen to come across a six-inch patent leather pair that you might have been inspired by on the runway, but stick in the back of your closet when it comes time to wear them.

Instead, I recommend opting for a flat or low-heeled boot in shades and materials you feel comfortable wearing.

Get a chic and trendy look by either wearing the pair with matching pants (black-on-black, tan-on-tan, etc.), or making a skirt or dress more weather appropriate by pairing a skinnier shaft boot to cover more leg.

Tanasha @stylisheights above looks incredible in her long red boots. She matches her boot color to the accents in her cardigan.

Check out this similar turtleneck top, cardigan, jeans, over the knee boots, belt and handbag.

How to look fashionable in winter: over the knee winter boots | 40plusstyle.com

DREAM PAIRS stretch over the knee bootKenneth Cole REACTION zip bootDREAM PAIRS block heel over the knee bootErmonn wide calf winter boot

4. Winter wear for women: Take a walk on the wild side

How to look fashionable in winter - which of these 11 ways do you use? | 40plusstyle.com

Style tip: For the winter months, (faux) fur is one of those sartorial no-brainers when it comes to keeping warm.

Faux fur or Shearling, when worn tastefully, can immediately elevate your look.

Consider substituting a peacoat or jacket for a fur coat. The change in texture creates a high end look that keeps you warm and au courant.

Terri @glammas.closet above (read her style interview here) looks fabulous in a faux fur trim coat and matching black boots.

Recreate her outfit with this similar coat, boots, handbag and floppy hat.

Winter outfits for women: warm faux fur coats | 40plusstyle.com

Karen Millen shearling fur cuff belted coatBellivera suede leather long jacketZLYC open front fur trim layers capeGRACE KARIN hooded fleece line coat

5. Winter attire: wear white to create classy winter outfits

Style tip: Most people will shy away from white during the winter months (especially those who ascribe to the post-Labor Day rule).

Much like the statement coats above, white jackets and coats can actually brighten a look and still feel winter appropriate.

Combinations of cream are incredibly popular here in Italy (where I’m now) and looks very sophisticated.

If that style is too monochrome for you, pair your white or cream pieces with darker prints or dark solids for a contrast that is still lively. If white is too pristine for you for winter, you could always opt for cream.

How to look fashionable in winter: white outfits for labor day and winter | 40plusstyle.com

CHICWISH check coatFunky Junque cable knit infinity scarfC.C warm soft glovesSam Edelman Chelsea bootAlepo winter beanie

6. Winter Looks For Women – make a statement

Looking fashionable in winter - a check coat outfit | 40plusstyle.com

Style tip: If you’re willing to make a statement with shoes, bags, and necklaces, a great next step is to make a statement with a coat.

Don’t give in to the temptation to mimic less than sunny days by going with dark coats and jackets.

Skip the gray and black and opt for a statement coat in either a bright hue or a bold print.

Marie-Louise @mrsmlmode above chooses a long, on-trend check coat.

Get her look with this similar sweater, coat, jeans, boots, shoulder bag and fedora.

Winter outfits for women: colorful statement jackets | 40plusstyle.com

Bellivera suede long jacketHalogen wool coatBoden wool blend coatKaren Millen check jacquard coat

For more tips take a look at this article on how to choose a winter coat.

7. Winter trends: The statement scarf

Style tip: Scarves are a winter must have and offer an opportunity to add color to a dark look.

Statement scarves can either be oversized or regular sized pieces, but they usually have a variety of textures and/or offer bright prints and colors.

If you notice that you have a very dark and/or plain look that needs a little more life to it, consider a statement scarf to create a higher impact look.

How to look fashionable in winter: statement scarves | 40plusstyle.com

Plum Feathers pashmina scarfZando plaid chunky scarfWoogwin plaid scarfKate Spade New York colorblock wool blend scarf

Take a look at this article for more tips on how to style a scarf.

8. Stylish winter outfits: Keep your head warm

Wear a beret to look stylish in winter | 40plusstyle.com

Style tip: During winter, quite a bit of your body’s heat can be lost by not protecting your head.

So, a hat is absolutely essential when the temperatures get really low.

Think of this as an opportunity to invest in a hat you know you will want to wear and that flatters both your look and face shape. And if you need tips on wearing them, check out our tips on how to wear a hat.

A great option for very cold weather is a quality faux fur trapper that you can keep for years. It will always be on trend for the winter and will most certainly keep you warm.

Another chic option is a wool wide brim hat. It keeps your face free, while the wool hat keeps your head warm.

Patricia @madamechicbcn above (read her style interview here) often wears hats to make an impact.

Steal her look with this similar sweater, jeans, pumps, crossbody bag, necklace, beret and sunglasses.

How to look fashionable in winter: keep your head warm | 40plusstyle.com

Lisianthus fedora hatZLYC wool french beretC.C cable knit beanieJeff & Aimy newsboy cap

Take a look at how to choose a hat to suit your face shape.

9. Winter outfits for women: Put a cape (or poncho) on it

How to look fashionable in winter - Psyche wears a monochrome poncho | 40plusstyle.com

Style tip: Capes or ponchos are always the perfect choice when you want a dramatic and chic piece that requires very minimal effort.

From jeans to leggings to dresses, a cape is a nice way of pulling a look together while still keeping you warm.

Opt for prints for more unique looks that are a departure from your classic cape styles.

As usual, pay attention to proportions when styling your cape. For many body shapes, keeping the bottom leaner and less bulky is key to pulling of this look.

Psyche @economyofstyle above chooses a monochrome outfit and adds a pop of red with her lipstick.

Recreate her outfit with this similar ruana, bootcut jeans, booties and earrings.

How to look fashionable in winter: Stylish capes and sweaters | 40plusstyle.com

Ferand knitted poncho topMELIFLUOS DESIGNED IN SPAIN shawl wrap ponchoNordstrom wool & cashmere capePULI versatile knitted poncho

10. Winter fashion ideas: Drape and belt

Style tip: Create dramatic shapes and flow by opting for a draped cardigan or wrap.

The additional material is a great option for keeping you warm and allowing you to feel like you are wrapped in a toasty blanket.

However, to keep it closed, either opt for a belted cardigan or select a coordinating or contrasting belt.

Pair the heavier, draped top with leggings, slim leg pants, or a sweater dress to create a more flattering silhouette that is not too bulky on the top and bottom.

Winter fashion ideas: Drape and belt | 40plusstyle.com

JJ Perfection open front long cardiganLARACE swing tunic topBP. high rise leggingsDREAM PAIRS block heel over the knee bootBOSTANTEN bucket bagC.C cable knit beanieFeluz wide waist belt

The poncho below comes with a belt meaning the look is ready made for you. Just add skinny jeans, a turtleneck and boots.

Moss Rose wrap poncho ruana | 40plusstyle.com

Moss Rose wrap poncho ruana

Also take a look at how to wear a belt.

11. Trendy winter outfits: All you need are gloves

Winter outfits for women - Josephine in bright pink gloves | 40plusstyle.com

Style tip: Long gloves are the perfect opportunity for you to wear shorter sleeve coats and jackets while shorter styles will look fabulous for everyday.

Don’t feel confined to wearing only black pairs, opt for some color that will not simply blend in but bring a life of their own to your look.

Josephine @chicatanyage above (read her style interview here) opts for pink leather gloves which match her paler pink jacket and hat.

Check out this similar sweater, puffer jacket, pants, booties, belt bag, beret and gloves.

How to look fashionable in winter: gloves for a chic winter outfit | 40plusstyle.com

Vislivin leather glovesC.C cable knit glovesBYOS plush knit glovesThe North Face leather gloves

Below, you can see all of the outfits from above together in one capsule.

A capsule wardrobe on how to look fashionable this winter | 40plusstyle.com

shop some of the items above here:

Which of these winter outfits for women would you wear? How do you stay both stylish and warm during the winter months? What other winter clothes tips do you have?

Continue reading:

  1. Christmas Day outfits – from day to evening
  2. The Best Winter Coats For Women This Season And How To Choose A Coat
  3. How to wear your sweaters with jeans this winter
  4. Cold Weather Outfits To Keep You Warm AND Stylish

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Winter outfits for women: How to look fashionable in winter | 40plusstyle.com

Feature image by Marie-Louise @mrsmlmode above

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