I have always worked in places that called for smart casual dress—whether it be grad school (which is definitely on the more casual side if you don’t teach) or real-world job. I lucked out in that most of the clothes I wore in grad school could translate to my job! “Smart casual” is essentially my style in a nutshell, and you’ll find tons of outfit inspiration if you browse CCCH. I consider smart casual to be slightly less formal than business casual. You want to be put together but don’t need to wear slacks.
It’s already tricky to dress for work in the winter because you have to deal with cold and snow and wind and whatever else the atmosphere may throw your way. Now you have to figure out how to deal with that while still looking polished. There are definitely a few items I reach for again and again in the winter months! (Thank goodness I don’t have a business formal dress code!)
I rounded up 16 past winter outfits that I would consider smart casual and that would work for any workplace or event that calls for a smart casual dress code. Take note of the similarities between each of the 16 outfits; there were a lot of overlapping themes and items that I picked up on while putting together this post. I shared a few tips for dressing smart casually in winter and some of those overarching themes to keep in mind below!
READ MORE: How to Dress Smart Casual in the Summer
How to Dress Smart Casual in the Winter
Smart casual combines the elements of casual wear (think jeans, lots of color, tees, etc.) and business attire (think tailored items, button-downs, comfortable yet presentable footwear, etc.). When it comes to dressing smart casual at your office or perhaps to a wedding or other special event, think about unexpected combinations (like blazer + jeans) and juxtapositions. In the winter, it’s especially fun to play around with different styling ideas (tucking/not tucking, belts, various types of boots) and sweater styles (cropped sweaters, billowy sleeves, fun textures, etc.) in particular!
Here are some of the items and themes you’ll see repeated over and over again in smart casual winter outfits and especially in the outfit roundup below:
Basic sweaters (of the fabric of your choosing; I personally love cashmere)
Dark wash denim (wear your favorite styles, even if they’re skinny jeans)
Boots (ankle or tall boots when it’s dry, snow boots when it’s wet/sloppy)
Tailored coat (your coat MAKES the outfit in the winter—have fun with it)
Darker colors (I tend to lean towards a moodier color palette when the weather is gloomy)
Monochrome color palettes (now is the time to play around with color combos)
The number one “rule” for dressing for a smart casual office or any dress code in general is you want whatever you wear to fit you. You don’t want any gapping or bulging or anything of that sort—if it you don’t feel confident, it’s not going to work! I recently had to purchase a few new items to fit my new pandemic body, and I love that I can feel comfortable and put-together in what I wear again.
Below, I rounded up 16 past smart casual winter outfits to serve as inspiration. You can probably make most of these with similar items in your own closet! If you click on each photo you’ll be taken to the original outfit post, and there’s a shopping widget below each outfit with exact or similar items if you’re in the market for a particular item.
I did not include any outfits with skirts or dresses as I just don’t have any that I can wear to the office in the colder months, but if you do prefer skirts and dresses, even in winter, I highly recommend investing in a pair of fleece-lined tights. They are game changers!
What is your favorite smart casual outfit to wear in winter? What’s your workplace dress code?
Read next: How to style a sweater blazer for work
Add a Topcoat to Any Outfit
Topcoats aren’t just for the men…! Add a tailored topcoat to essentially any outfit and you will instantly look smart casual. It’s magic and seriously the easiest thing to do! I’m wearing mine here over a basic cashmere sweater and paperbag pants, and both items can be dressed up easily. The chocolate brown ankle boots ground the outfit and keep it from feeling too heavy or dark.
Camel + Chocolate Brown
I’m actually wearing the same coat and boots in the outfit above, so you already know this is a great smart casual combination! There’s something about shades of brown that ties everything else together. Here, I’m wearing a classic cashmere crewneck sweater in a blush pink color and dark wash demi-boot jeans (the fraying at the hems makes it look like you don’t take yourself too seriously).
Shades of Brown and White
One of the easiest ways to instantly look smart casual is to wear complementary colors. This outfit features colors on the lighter end of the spectrum: a camel coat over an ivory sweater and white denim base. Adding cognac brown ankle boots that coordinate with your bag makes you look extra polished in case you also rolled out of bed after hitting snooze 5 times (not that I can relate or anything… 🙈).
Tonal Coat + Sweater
Here’s another smart casual outfit but with dark complementary colors (and monochrome on the top half!): dark red and burgundy, dark wash denim, and black shiny leather boots. These first four outfits all featured wool coats, which are excellent options for taking your winter outfits up a notch. They can truly make any casual winter outfit you wear look polished and intentional.
Matching Shoes and Bag
This outfit is more on the casual side of smart casual, but I still included it here because the base of the outfit has so many of the same smart casual elements: a nicer sweater (chenille is such a fun texture), medium wash jeans, and, of course, cognac brown ankle boots and the coordinating tote. I wore a lightweight puffer coat here because, well, it’s winter; I definitely recommend a warm coat for commuting!
Long Cardigan + Tall Boots
This outfit might also feel on the more casual side of smart casual depending on your office. In the winter, I’m all about layering sweaters to maximize comfort and warmth! A thin merino wool sweater works perfectly under a chunky knit cardigan (you could also opt for a longer sweater blazer instead!). Even though I wore dark jeans, I kept this outfit on the warmer side by wearing brown tall boots.
Add Velvet Elements
A velvet peplum tank instantly elevates a plain black blazer, and adding black velvet ankle boots takes the whole outfit up a notch! This is the perfect smart casual workwear outfit idea during the holiday season in particular—you’ve got that hint of berry red in addition to the lovely velvet textures. Notice how I kept the entire outfit on the dressier side by wearing dark wash denim.
Opt for Sweater Blazers
A typical structured wool blazer often feels too stuffy for smart casual workplaces or dress codes (though you can always opt to “dress down” a structured blazer)! Instead, opt for the smart casual counterpart: the sweater blazer! Mine get so much wear because they make me feel put together but also comfortable. I particularly like layering mine over patterned tops and shirts.
Wear Colorful Pants
You can definitely get away with wearing colorful pants with a smart casual dress code! My recommendation is to stick with colors that could be considered neutrals, i.e. burgundy, olive green, navy, grey, brown, etc. (Wear what coordinates with your wardrobe!) It’s super fun to dress them up with a lightweight sweater layered under a knit blazer as shown here. The shiny black boots anchor the outfit.
Layer Your Sweaters
Here’s another fun smart casual (monochrome) outfit idea with colorful pants! It’s fun to pair colorful pants with coordinating tops and sweaters. I made this outfit extra dressy by layering a sleeveless collared shirt underneath the sweater. Did tall boots ever go out of style? I definitely feel like they’re classics, but I also live in Idaho which is most definitely not the fashion capital of the US haha!
Cropped Sweater + Ponte Pants
When it comes to dressing smart casual, all “rules” can go out the window if you wish! I particularly love making cropped sweaters work-appropriate by layering a sleeveless collared shirt underneath (much like what I wore in the previous outfit). This outfit also features ponte pants, which can also most definitely be worn to the office! (Read my tips for wearing ponte pants to work!)
Wear Dark Wash Denim
Definitely one of the overarching themes in the majority of these outfits is to wear dark wash denim. When I think smart casual, I think dark wash denim. (I do wear other washes to the office, but dark wash is what I reach for on days that involve meetings or conferences with external partners.) This outfit is simple yet impactful; it’s another example of layering a fun top under the cropped sweater!
Go Monochrome
Can you tell I really love wearing monochrome outfits in the winter? This one is an unexpected brown color combination—and I picked a black belt and black ankle boots to keep it grounded and intentional. While I’m a fan of the front tuck in most situations, sometimes an outfit calls for a good full tuck. Doing so makes sure that the black belt is visible and visually breaks up the all-brown ensemble.
Flannel Button-Down Shirt
Winter is not the time you want to wear those crisp, stuffy button-down shirts that you’d typically wear to the office. Instead, opt for cozy flannel button-down shirts! Flannel shirts can work for a smart casual workplace with the right pants and shoes—and you probably know by now exactly how you’d style one after seeing all these outfit ideas! I enjoyed mixing it up and tucking mine into my wide leg crop pants.
Wear Warm Neutrals
Another popular theme in this roundup of smart casual winter outfits is warm neutrals! It’s so easy for me to automatically gravitate towards all black everything because it’s dark and grey outside all winter, but I’ve been loving making it a point to wear more creams and browns. I look like a warm cup of chai when I wear warm neutrals, which is exactly what I want to drink every day of winter.
Sweatpants? Yes, Really
Okay, so, your workplace might not be casual enough for sweatpants—but don’t these look office-appropriate? Can you believe they’re sweatpants? If your office is on the casual side of business (or smart) casual, keep your eyes peeled for sweatpants that can pull double duty at work. If nothing else, they’re perfect WFH pants: you’ll feel polished in an outfit like this but totally comfy at the same time!
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Kimi, Cotton Cashmere Cat Hair
outfit roundup, workwear
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Insights, advice, suggestions, feedback and comments from experts
As an expert in fashion and dressing for different dress codes, I can provide insights and information related to the concepts used in this article. Let's dive into each concept mentioned:
Smart Casual Dress Code: Smart casual combines elements of casual wear and business attire. It is slightly less formal than business casual but still requires a put-together look. When dressing smart casual, you can experiment with unexpected combinations and juxtapositions. In the winter, you can play around with different styling ideas, such as tucking or not tucking, belts, various types of boots, and different sweater styles.
Winter Workwear: Dressing for work in the winter can be tricky due to the cold, snow, and wind. It's important to stay warm while still looking polished. Some key items to reach for during the winter months include basic sweaters (such as cashmere), dark wash denim, boots (ankle or tall boots depending on the weather), and a tailored coat. Darker colors and monochrome color palettes are often preferred in the winter.
16 Smart Casual Winter Outfit Ideas: The article mentions 16 past winter outfits that are considered smart casual and suitable for any workplace or event that calls for a smart casual dress code. Some common themes and items observed in these outfits include basic sweaters, dark wash denim, boots, tailored coats, darker colors, and monochrome color palettes.
Fit and Confidence: The number one rule for dressing smart casual or any dress code is to wear clothes that fit well. It's important to avoid any gapping or bulging and to choose clothes that make you feel confident. The article emphasizes the importance of feeling comfortable and put-together in what you wear.
Additional Tips: The article also suggests investing in fleece-lined tights for wearing skirts or dresses in winter, adding a tailored topcoat to instantly elevate any outfit, wearing complementary colors to achieve a smart casual look, and layering sweaters for warmth and style. It also mentions specific outfit ideas, such as adding velvet elements, opting for sweater blazers instead of structured wool blazers, wearing colorful pants, and going for monochrome outfits.
Overall, the article provides inspiration and guidance on how to dress smart casual in the winter, with specific outfit ideas and tips to create a polished and stylish look while staying warm and comfortable.
