Here, I’m going to talk you through 19 comfy and casual winter outfits. I love effortless and timeless style, but I’m not fond of the cold. Finding the perfect balance between keeping warm and looking chic is something I’ve worked on for many years, and now I think I’ve got it spot on.
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Cashmere sweater in black & cream for winter
1. Cashmere
One surefire way of staying stylish in winter is to invest in some cashmere. I went for a cashmere sweater with black and cream stripes, and a roll neck to protect me from the wind.
I’ve kept it classic with black cords and a wool coat for another layer.
Casual winter outfit with a knit jacket
2. Knit jacket
This jacket has a timeless, Parisian style that feels up to date at the same time. Though it’s an easy one to dress up, for casual winter days, I’ve been styling it like this.
It’s a bit of a high-low approach that contrasts with the laid-back vibe of my knit.
Wearing menswear-inspired shapes in winter
3. Menswear shapes
Here, I’m wearing a gorgeous zip jumper. I couldn’t resist the shade, and the chunky knit in a menswear-inspired shape really suits my style. I’ve paired it with tailored trousers to smarten up the look.
Layered winter outfit with a wrap coat
4. Wrap coat
To get the balance between chic, comfortable, and warm just right, my method comes down to layers.
There is something understatedly sexy about being wrapped up in a gorgeous coat, so you can easily make the look work in your favor.
Casual winter outfit with an oversized jacket
5. Oversized jacket
Something that has proved surprising wearable in my capsule wardrobe is this super-toasty wool jacket.
I love the oversized shape and the high collar. A splash of this season’s winter green is the icing on the cake.
I style it with Breton stripes for casual days, and the color really pops when I wear it against black.
Comfy winter outfit with a tailored coat
6. Tailored coat
A go-to winter look for me is a great pair of jeans and a jumper. An easy way to make that outfit more stylish would be to add a tailored coat over the top.
I’ve opted for a timeless camel trench. My other layers are keeping me warm, so I tend to choose my coat with looks like this from an aesthetic point of view, rather than practical reasons.
Classy winter outfit with skinny jeans
7. Skinny jeans
This is the kind of look that I would wear to a Christmas party. Skinny jeans because, on-trend or not, they make my legs look longer. I wear heels for the same reason.
I’ve styled them with a simple striped shirt and blazer to finish.
Casual winter outfit contrasted with a coat
8. Contrast
Quite the opposite now and very much my daytime chic look, keeping things simple with jeans and a cotton shirt.
When I’m opting for comfort, which I am here with my Nikes on my feet, I like the contrast of a beautiful winter coat over the top. It instantly makes my super-chilled outfit feel more put together.
Fall-to-winter dress outfit
9. Fall dress for winter
There’s no reason why you can’t reach for autumnal dresses in winter; it’s just a matter of playing with the styling and adding a few more layers to make it work.
Here, I’m wearing a dress with no sleeves, but I’m not put off wearing it whatever the weather. I’ve been styling it with one of my favorite wool blazers, tights, and little black ankle boots.
All-white tonal winter outfit
10. Tonal outfits
A little tonal love for you now. You can look chic and timeless very easily this winter by wearing variations of a similar tone.
It doesn’t have to be white, you could opt for camel or burgundy if that’s your cup of tea.
Casual winter outfit for warmer climates
11. Blouse, blazer & flats
Milder winters warrant fewer layers, so those of you in warmer climates can get away with a blouse and a blazer at this time of year.
I’ve had a lot of wear out of these pointed-toe ballet flats; they’re so comfy it’s like wearing slippers.
How to dress well in winter
12. Light-colored blazer
Here, I’ve paired jeans with a simple cashmere crew neck for a classic go-to outfit.
I’ve finished the outfit with a gorgeous blazer, the shade lifts the tone of my whole outfit and the texture adds more depth to something that otherwise would be quite plain.
Chic winter outfit in tones of gray
13. Shades of gray
Another tonal mix now, but not quite as exaggerated as my white version. This time I’ve opted for more of a subtle approach, integrating different shades of gray into my outfit idea.
If you look at everything I’m wearing as individual pieces, you’ll notice that they’re all pretty classic and timeless items.
When styled together, they become a melting pot of effortless style meets comfy winter days.
Winter outfit with ankle boots
14. Light-wash jeans
Even more casual now but hopefully no less chic. Here I’ve styled beige ankle boots with my cashmere jumper and straight-fit light wash jeans finished with a cream coat.
Comfy and casual winter white outfit
15. Winter whites
Winter whites again, this time styling a lovely wool blend pair of pleated trousers.
On my top half, I’m wearing a cashmere rollneck that I sized up to a medium to get that oversized fit and my faithful double-breasted coat to finish.
Winter outfit in camel tones
16. Camel tones
Of course, my love of camel tones needed to sneak in somewhere. This cardigan is one of the most versatile pieces of knitwear I own.
I wear it as a cardigan, back to front as a jumper, knotted at the front to definite my waist, tucked in, half-tucked, and left open with a casual tee. There are so many ideas with just this one piece.
Comfy winter outfit with a backward cardigan
17. Wearing a cardigan backwards
Back to my favorite flats, but this time styling them with smarter tailored trousers for a little more polish. I’m wearing one of my knits back to front as a jumper.
How to wear a cardigan backwards
I like the understated sexiness of seeing a touch of skin at the back, though that dip to the first button is definitely high enough to get away with a bra underneath.
Parisian-inspired winter outfit
18. Parisian style
Here I’m wearing a stunning, one-of-a-kind buttoned navy velvet jacket.
It feels a little bit Parisian, perhaps with a sprinkle of bohemian spirit, and styled with causal jeans and ankle boots make it stand out even more.
Comfy & casual winter outfit with a coat
19. Wintergreen
Back to my wintergreen coat, but this time sharing how lovely that tone looks against camel shades. It feels rich and sumptuous, and the mix of textures adds interest.
I’ve styled them with my gray wash straight jeans and a lovely tanned tote.
Comfy & casual winter outfits
I really hope you’ve enjoyed my 19 chic and comfy winter outfits. Let me know which was your favorite look in the comments below.
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Insights, advice, suggestions, feedback and comments from experts
As an expert in fashion and style, I can provide you with information related to all the concepts used in this article. Let's go through each concept and discuss them in detail:
Cashmere Sweater: Cashmere is a luxurious and soft fabric made from the wool of cashmere goats. Cashmere sweaters are known for their warmth, softness, and durability. They are a popular choice for winter outfits due to their ability to keep you cozy and stylish at the same time.
Knit Jacket: Knit jackets are versatile and timeless pieces that can add a touch of elegance to any outfit. They come in various styles and materials, ranging from chunky knits to finer weaves. Knit jackets are perfect for casual winter days when you want to stay warm and stylish.
Menswear-Inspired Shapes: Menswear-inspired shapes refer to clothing items that are traditionally associated with men's fashion but are adapted for women's wear. This can include oversized or boxy silhouettes, tailored trousers, and structured pieces. Incorporating menswear-inspired shapes into your winter outfits can add a fashionable and sophisticated touch.
Wrap Coat: A wrap coat is a coat style that features a wraparound closure, often secured with a belt or tie. This type of coat is known for its elegant and feminine look. Layering with a wrap coat can help you achieve a balance between chic, comfort, and warmth during the winter months.
Oversized Jacket: Oversized jackets are characterized by their loose and relaxed fit. They provide a cozy and trendy look, especially when made from warm materials like wool. Pairing an oversized jacket with other casual pieces, such as Breton stripes, can create a stylish winter outfit.
Tailored Coat: A tailored coat is a classic and versatile piece that can elevate any winter look. It is typically well-fitted and structured, with clean lines and minimal embellishments. Choosing a tailored coat in a timeless color like camel can give your outfit a polished and sophisticated appearance.
Skinny Jeans: Skinny jeans are a popular denim style characterized by their tight fit from the waist down to the ankles. They are known for their flattering and elongating effect on the legs. Pairing skinny jeans with a striped shirt and blazer can create a classy and put-together winter outfit.
Contrast: Adding contrast to your outfit involves incorporating elements that stand out or create visual interest. This can be achieved by combining different textures, colors, or styles. For example, contrasting a casual outfit with a beautiful winter coat can elevate the overall look.
Fall-to-Winter Dress Outfit: Transitioning your fall dresses into winter can be done by layering and adding warmer accessories. Pairing a dress with a wool blazer, tights, and ankle boots can make it suitable for colder weather while maintaining a stylish appearance.
Tonal Outfits: Tonal outfits involve wearing variations of a similar color or tone. This can create a chic and cohesive look, whether it's all-white, camel, burgundy, or any other color palette you prefer. Tonal outfits are an easy way to achieve a timeless and sophisticated winter style.
Blouse, Blazer & Flats: In milder winter climates, you can opt for a more lightweight and layered approach. Pairing a blouse with a blazer and comfortable flats can create a polished and effortless winter outfit suitable for warmer weather.
Light-Colored Blazer: Adding a light-colored blazer to your outfit can bring a touch of sophistication and elevate a simple look. The color of the blazer can add depth and interest to an otherwise plain outfit.
Shades of Gray: Incorporating different shades of gray into your outfit can create a subtle and elegant winter look. Mixing classic and timeless pieces in various shades of gray can result in an effortless and comfortable style for winter.
Ankle Boots: Ankle boots are a versatile and popular footwear choice for winter. They come in various styles, from casual to dressy, and can be paired with different outfits to create a trendy and fashionable look.
Winter Whites: Winter whites refer to wearing white or off-white clothing items during the winter season. Styling wool blend trousers, a cashmere rollneck, and a double-breasted coat in winter white can create a cozy and chic winter outfit.
Camel Tones: Camel tones are warm and neutral colors that can be incorporated into winter outfits for a sophisticated and timeless look. A versatile cardigan in camel can be worn in multiple ways, adding versatility and style to your wardrobe.
Wearing a Cardigan Backwards: Experimenting with different ways to wear a cardigan can create unique and fashionable looks. Wearing a cardigan backwards can provide an understated and sexy touch to your outfit.
Parisian Style: Parisian style is known for its effortless and chic aesthetic. Incorporating Parisian-inspired pieces, such as a navy velvet jacket, into your winter outfits can add a touch of sophistication and individuality.
Wintergreen: Wintergreen is a rich and vibrant shade of green that can be incorporated into winter outfits for a pop of color. Pairing wintergreen pieces with camel shades and gray wash jeans can create a stylish and cozy winter look.
I hope this information helps you understand the concepts used in the article and provides you with insights into creating comfy and casual winter outfits. If you have any specific questions or need further assistance, feel free to ask!
