How to look fashionable in winter – Which of these 10 ways do you use?

by Sylvia

How to look fashionable in winter |

Winter can be one of the most challenging seasons to consistently wear chic looks that are both weather appropriate and figure flattering. When the primary motivation is keeping warm while facing more dreary and less sunny days, the temptation is there to simply throw together as many pieces as possible and get out the door.

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 10 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.

10 ways to stay chic this winter

1. Layer, layer, layer

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, 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 playing with varying lengths to flatter your body shape.

How to look fashionable in winter: chic layering outfit pieces |

2. Go over the knee

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

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

3. Take a walk on the wild side

Style tip: When it comes to winter months, (fake) fur is one of those sartorial no-brainers when it comes to keeping warm. From faux fur options all the way to fox fur,  fur pieces (when worn tastefully) immediately elevate your look.

Consider substituting a peacoat or jacket for a fur coat. The change in texture creates a more high end look that keeps you warm and au courant with this season’s trends.

How to look fashionable in winter: warm faux fur coats and scarves |

4. 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 (such as the pink J. Crew gem below) or a bold print (such as the leopard print coat below).

The key to pulling this look off is by keeping the rest of your look neutral and simple. Let the coat do all the talking.

How to look fashionable in winter: colorful statement jackets |

5. Wear white

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.

Pair your white piece with darker prints (such as the dark floral print pencil skirt below) or dark solids for a contrast that is still lively.

How to look fashionable in winter: white outfits for labor day and winter |

6. 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.

A great option for very cold weather is a quality fur trapper (real or faux fur works) 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.

How to look fashionable in winter: fashionable hats for the winter |

7. Drape and belt

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

How to look fashionable in winter: draped cardigans and belts for a chic winter outfit |

8. 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 (such as the fur scarf below) 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 |

9. Put a cape on it

Style tip: Capes 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 (such as the Ted Baker and Alice + Olivia pieces) below 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 sweaters |

10. All you need are gloves

Style tip: Long gloves are the perfect opportunity for you to wear shorter sleeve coats and jackets.

Don’t feel confined to wearing only black pairs, opt for some color (like the pink and brown pairs below) that will not simply blend in but bring a life of their own to your look.

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

Shop the pieces and looks featured in this post here below.

How do you stay both stylish and warm during the winter months? What other tips do you have?



Related posts:

{ 9 comments… read them below or add one }


This is a fabulous post that really details a lot of options I use for Fall/Winter. Recently my daughter 25 and I have been talking and shopping for Statement Sweaters and Toppers. I would have to say I use all of these ideas. Over the knee boots are tough to style for my petite height, but that didn’t stop me from trying, lol
If I had to choose a favorite it would have to be #7, without the belt.



This is a great post. I love fall clothes because there are so many ways to put together outfits, like you just showed in the post. One of my favorite ways is to layer with cardigans and sweaters. I also recently bought a cape and I love the way it keeps me warm and looks chic.



Hello, I’m Lisa and I have a scarf addiction….

I LOVE winter because I get to pull out all the scarves! Often I start with the scarf and create the other layers to go with it. I think that has encouraged me to some more daring color combinations over the years.



Thanks for so many ideas! Winter is fast approaching where I live. I got a chance to wear a fur vest with boots yesterday when the temperature barely reached 50 degrees F. I will be layering and need to shop for some new first layer tops to go under jackets and sweaters. Interesting boots, hats and colorful scarves are my go to items to bring life to dull clothes. This season I hope to buy a colorful coat to supplement my outerwear choices.



I still find layering difficult. When I create an outfit with layers than that is for a reason. You cannot just remove the statement scarf “which pulls everything together”. That is my problem.



Finally wearing boots again!!! Yeah.



Dear Sylvia,
What a great post to read!
I’ve been waiting for something exactly like this.
I need to refresh my Autumn/Winter wardrobe. With your advice I can do it now so much easier.

Thank you so much!



Layering can be tough. Not so easy to layer different types of clothes without looking like a Bibendum 😉 !!



Thank you…. Always looking for tips on how to style the wardrobe for Winter. I am from California but moved to Germany.


Leave a Comment

Previous post:

Next post: