Best Clothes For Working Outside In Winter – I’ve always worked in places that require smart casual dress – whether it’s high school (which is definitely on the more casual side if you’re not teaching) or work in the real world. I was lucky that most of the clothes I wore in high school could translate to my job! “Smart casual” is basically my style in a nutshell, and you’ll find plenty of outfit inspiration if you browse CCCH. I consider smart casual to be a little less formal than business casual. You want to be tied up, but you don’t have to wear long pants.
Dressing for work in the winter is already hard because you have to deal with the cold and the snow and the wind and whatever else the mood can throw at you. Now you need to know how to handle it while still looking polished. There are definitely some items I reach for again and again during the winter months! (Thank God I don’t have a formal business dress code!)
Best Clothes For Working Outside In Winter
I rounded up 16 outfits from the past season that I would consider smart casual and would work for any workplace or event that requires a smart casual dress code. Notice the similarities between each of the 16 outfits; there are many overlapping themes and items that I found when putting this article together. I share some tips for casual winter dressing and some important themes to keep in mind below!
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Smart casual combines the elements of casual wear (think jeans, lots of colors, t-shirts, etc.) and business wear (think tailored items, button-downs, comfortable but neat footwear, etc.). When it comes to a smart casual dress for your office or perhaps for a wedding or other special event, think about unexpected combinations (like blazer + jeans) and juxtapositions. In winter, it’s especially fun to play with different styling ideas (tucking / not tucking, belts, different types of shoes) and sweater styles (cut sweaters, billowing sleeves, fun textures, etc.)!
Here are some of the items and themes you’ll see repeated in smart casual winter wear and especially in the collection below:
The number one “rule” of dressing for a smart casual office, or dress code in general, is that you want whatever you’re wearing to fit you. You don’t want gaping or bulging or anything like that – if you’re not sure, it won’t work! I recently had to buy a few new things to fit my new pandemic body and I love that I can feel comfortable and put what I’m wearing back together.
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Below I have collected the latest 16 smart casual outfits for inspiration. You can probably make many of these with similar items in your own closet! Clicking on each image will take you to the original outfit post and there is a shopping widget below each outfit with the exact or similar item if you are looking for a specific item.
I didn’t include skirts or dresses because I don’t have anything I can wear to the office in the colder months, but if you like skirts and dresses even in winter, I highly recommend investing in a pair of lined tights hair They are game changers!
And you’ll instantly look smartly casual. This is magic and seriously the easiest thing to do! I wear mine here with a basic cashmere sweater and paper bag pants, and both can easily be dressed up. Chocolate brown ankle boots soften the outfit and prevent it from feeling too heavy or dark.
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I actually wore the same coat and shoes in the outfit above, so you already know this is a smart casual combo! There is something about shades of brown that ties everything else together. Here I’m wearing a classic blush pink crew neck cashmere sweater and dark wash demi-boot jeans (the bulky bottom keeps you from standing up.
One of the easiest ways to instantly look smart casual is to use complementary colors. This outfit features colors on the lighter end of the spectrum: a camel jacket over an ivory sweater and a white denim base. Adding cognac ankle boots that coordinate with your bag will make you look even more polished if you’re also rolling out of bed after hitting snooze 5 times (not that I can relate or anything… 🙈).
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 shiny black leather shoes. These first four outfits are all made with wool coats, which are a great choice for your winter wear. It can really make any casual winter outfit you wear look polished and deliberate.
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This outfit is more on the relaxed side of smart casual, but I’m still including it here because the basic outfit has so many smart casual elements: a nice sweater (chenille is like a fun texture), medium wash jeans, and of course, cognac ankle boots and a coordinating tote. I’m wearing a light puffer jacket here because it’s winter; I definitely recommend a warm jacket for commuting!
This outfit can also feel on the more relaxed side of smart casual depending on your office. In the winter, I’m very into layering sweaters to maximize comfort and warmth! A thin merino wool sweater can be worn under a chunky knit cardigan (you can also opt for a longer sweater blazer!). Even though I was wearing dark jeans, I kept this outfit on the warmer side by wearing brown boots.
A velvet peplum tank instantly elevates a plain black blazer and adding black velvet boots takes the whole outfit up a notch! This is a smart casual workwear idea that’s perfect for the holiday season in particular – you’ve got hints of berry red in addition to a lovely velvety texture. Notice how I kept the whole outfit on the dressier side by wearing dark wash denim.
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A typical structured wool blazer often feels too much for a smart casual workplace or dress code (although you can always opt for a “dress down” structured blazer)! Opt for a smart casual pair instead: a sweater blazer! Mine gets a lot of wear because it keeps me together but also comfortable. I especially like layering mine over patterned tops and shirts.
You can definitely get away with colorful pants with a smart casual dress code! My recommendation is to stick with colors that can be considered neutrals, i.e. burgundy, olive green, navy blue, gray, brown, etc. (Wear what fits your wardrobe!) It’s super fun to dress them up with a light sweater layered under a knit blazer as shown here. Shiny black shoes anchor the wardrobe.
Here’s a fun smart casual (monochrome) idea with colorful pants! It’s fun to combine colorful pants with coordinating tops and sweaters. I made this outfit more elegant by layering a sleeveless collared shirt under the sweater. Do tall boots ever go out of style? I definitely feel like they are classy, but I also live in Idaho, which is definitely not the fashion capital of the US haha!
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When it comes to smart casual clothing, all the “rules” can go out the window if you want! I really like to make a cropped sweater fit by layering a sleeveless collared shirt underneath (like the one I wore in the previous outfit). This dress also has ponte pants which can be worn to the office too! (Read my tips for wearing trousers to work!)
Definitely one of the overarching themes in most of these outfits is wearing dark wash denim. When I think smart casual, I think dark wash denim. (I have other washes in the office, but the dark wash is what I reach for on days that involve meetings or conferences with external partners.) This outfit is simple, yet effective; it’s another example of layering a fun top under a cropped sweater!
Can you tell I really like wearing monochrome clothes in the winter? It’s an unexpected brown color combination – and I chose a black belt and black ankle boots to keep it grounded and deliberate. While I’m a fan of the front tuck in most situations, sometimes an outfit calls for a full tuck. Make sure the black belt is visible and visually break up the all-brown ensemble.
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Winter is not the time when you want to wear those crisp, thick button-up shirts that you usually wear to the office. Choose a comfortable flannel shirt with buttons instead! A flannel shirt can be worn for a smart casual workplace with well-fitting trousers and shoes – and you probably now know what your style looks like after looking at all these outfit ideas! I like to mix it up and tuck mine into wide leg pants.
Another popular theme in this collection of smart casual winter wear is warm neutrals! It’s so easy for me automatically
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