Winter can be one of the most challenging seasons to consistently wear winter outfits for women that are both weather appropriate and figure flattering, but the tips on how to look fashionable in winter will help.

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 13 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.

14 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.

Reviewers of the base layer thermals (below) say they are good quality, well made and comfortable to wear.

Mrignt Base Layer Thermal Tops 2 Pack |

Mrignt Base Layer Thermal Tops 2 Pack

If you want to stay extra warm, you may also want to wear thermal leggings under your outfit, so a thermal set would be perfect. The fleece set (below) comes in a good choice of colors, and wearers say it is soft and warm.

Thermajane fleece lined thermal set |

Thermajane Fleece Lined Thermal Set

2. Layer, layer, layer for winter style points

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.

An easy way to layer is to wear a poncho or wrap over your sweater. You can always add a camisole under any of your outfits to keep warmth in.

Winter layering ideas for winter outfits for women |

ZLYC Open Front Faux Fur Trim Cape PonchoMassimo Dutti Satin ShirtHudson Jeans Barbara Super Skinny JeansSeychelles Gifted Over-The-Knee BootLongchamp ‘Mini Le Pliage’ HandbagBrinker + Eliza Wendy Gold Fill & Pearl Huggie Hoops

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 |

Dawn Levy Madrid Striped Wool Faux Fur JacketNatori Draped Asymmetric ShirtHudson Jeans Barbara Vegan Leather Bootcut JeansFranco Sarto Waxton Square Toe Bootieskate spade new york Hudson Pebbled Leather Convertible Shoulder BagRUOFFETA Velvet Twisted Earrings

Carmen in a pink sweater and jeans |

Carmen @carmen_gimeno above wears a shirt under her sweater. Depending on the weather you could always add a camisole and thermal leggings too.

Check out this similar sweater (another option here), shirt, coat, jeans, sneakers, handbag and sunglasses.

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

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 when putting together your winter outfits for women. The change in texture creates a high end look that keeps you warm and au courant. Look out for coats and jackets that are completely faux fur, or with a faux fur collar.

Winter outfits for women: warm faux fur coats |

Michael Kors Faux Fur JacketBelliver Suede Moto Jacket – Dawn Levy Madrid Striped Wool Faux Fur JacketZLYC Open Front Faux Fur Trim Cape Poncho

4. Go over the knee to create stylish winter outfits

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 longer shaft boot to cover more leg.

How to look fashionable in winter: over the knee winter boots |

Calvin Klein Jotty Over-The-Knee BootSeychelles Gifted Over-The-Knee BootNaturalizer Kyrie Water Repellent Over-The-Knee-BootLucky Brand Calypso Boots

5. latest boot trends

Sometimes just switching your shoes or your accessories can make a big difference to your existing outfits. Look out for the latest boot trends, and add an off-the-moment style to your wardrobe for an instant update. Styles to look out for this season include chunky soles, red or burgundy, and lace-ups.

Take a look at these Fall winter 2023 boot trends for more inspiration.

Latest trend boots |

Steve Madden Calabria Ankle BootFranco Sarto Waxton Square Toe BootiesBella Vita Danielle BootieSorel Hi-Line Heel Lace Boots

Winter outfits for women: How to look fashionable in winter |

Eugenia @theeageofgrace above (read her style interview here) matches her boots to her dress.

Steal her look with this similar dress, coat, boots, handbag, scarf, earrings and sunglasses.

6. 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 and white look sophisticated and unexpected for winter.

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 |

Loulou Studio Martil Wool-Cashmere CoatUGG Joselyn Lounge CardiganTory Burch Double T Cobat BootsJane Carr Cosmos Cashmere-Blend ScarfLanzom Classic Wide Brim Floppy Panama Hat – Saks Fifth Avenue Pom-Pom Cashmere Slouch BeanieNappaglo Nappa Leather Gloves

7. Latest sweater styles

It’s likely you’ll want to add at least one new sweater to your closet when the weather turns cooler. So, it makes sense to choose something on-trend in order to update your casual outfits. Look out for asymmetrical details, bright shades and fluffy textures.

Latest sweater styles |

Saks Fifth Avenue COLLECTION Mock Turtleneck Rib-Knit SweaterDesign History Whipstitch Relaxed TurtleneckMisook Boxy Knit Landscape SweaterCinq à Sept Lilliana Asymmetric Fringe Sweater

8. Winter Looks For Women – make a statement

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, jewel shade, or a bold print.

Winter outfits for women: colorful statement jackets |

Elie Tahari Adi Belted Wool-Blend CoatKaren Millen Italian Wool Blend Fitted Single Breasted CoatSam Edelman Wool Blend Notch Collar CoatBoden Canterbury Interest Coat

Winter outfits for women - Nikki in long coat, pants, boots and beanie |

Nikki @40notfrumpy above chooses a beautiful burgundy shade for her winter coat.

Steal her look with this similar top, coat, pants, boots, crossbody bag and beanie.

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

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

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.

How to look fashionable in winter: Stylish capes and ponchos |

rag & bone Trench Wool PonchoNIC+ZOE Cozy Reversible Jacquard PonchoPULI Versatile Knitte PonchoPULI Large Wrap Front Poncho

10. Trendy winter outfits: All you need are gloves

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 or a pattern that will not simply blend in but bring a life of their own to your look.

How to look fashionable in winter: gloves for a chic winter outfit |

Nordstrom Cashmere Lined Leather Touchscreen GlovesTory Burch T Monogram Toggle GlovesCarolyn Rowan Collection Celestial Embroidered Leather GlovesC.C Cable Knit Anti-Slip Touchscreen Gloves

11. Stylish winter outfits: Keep your head warm

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.

Stylish options include beanie styles and berets.

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

How to look fashionable in winter: keep your head warm |

Lisianthus Belt Buckle Fedora HatZLYC Reversible Beret Hatrag & bone Blake Logo Patch Wool Blend Rib BeanieNordstrom Recycled Cashmere Pom Beanie

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

Winter outfits for women: Jona in poncho and leggings |

Jona @the50plusgirl above combines layers, a chic hat and ankle booties.

Recreate her outfit with this similar shirt, poncho (another option here), leggings, boots and hat.

12. 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 |

maamgic Pashmina ScarfVince Boiled Cashmere Knit ScarfGanni Rib Wool Blend ScarfTreasure & Bond Plaid Blanket Scarf

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

13. 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 |

Caracilia Long Knit Cardigan – Mango High Collar T-ShirtJ.Crew Full-Length Sydney Wide Leg PantsFranco Sarto Waxton Square Toe Bootieskate spade new york Hudson Pebbled Leather Convertible Shoulder BagJ.Crew Plaited Italian Leather BeltLisianthus Belt Buckle Fedora Hat

Also take a look at how to wear a belt.

14. Add some leather

Adding texture to your outfit is a great way to create interest. Plus, leather can actually be super practical for winter as it keeps out the wind and cold weather.

How to look fashionable in winter: add some leather |

Hudson Jeans Oversized Faux-Leather ShirtModern Citizen Pilar Belted Vegan Leather Midi DressHudson Jeans Barbara Vegan Leather Bootcut JeansElie Tahari The Rumi Vegan Leather Midi-Skirt

Winter outfits for women: | Nancy in an all black outfit ensemble

Nancy @nancysstyle above (read her style interview here) wears her leather jacket with a midi skirt and booties.

Check out this similar sweater, moto jacket, skirt (another option here), booties, handbag, earrings, necklace and sunglasses.

Your fashionable winter outfits together in one capsule

Below, you can see all of the outfits from above together in one capsule, which should give you plenty of inspiration if you are thinking about how to look fashionable in winter. You can see that all of the colors in the capsule below go together so you can easily mix and match to create more outfits.

A capsule wardrobe on how to look fashionable this winter |

Shop the best winter outfits here:

Previous winter capsules

Below are previously created winter capsules. And, while many of the items are past season, you may still find they give you some ideas if you’re shopping your closet.

A capsule wardrobe on how to look fashionable this winter |
A capsule wardrobe on how to look fashionable this winter |

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. Cold Weather Outfits To Keep You Warm AND Stylish

Like this article on winter outfits for women? Share it on Pinterest

Winter outfits for women: How to look fashionable in winter |

Feature image by Carmen @carmen_gimeno


Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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