The way you dress in the wintertime is important, and it’s doubly so when you’re in a professional environment. One of the most difficult challenges of winter dressing is figuring out what to wear that will be both warm and formal enough to be appropriate for work. Fortunately, it’s not all that difficult; the key is balancing the warmth of your clothes with their level of formality.
There’s nothing worse than walking into a meeting, presentation, or networking event in the winter with your face buried in the hood of your sweatshirt. You might not be cold, but you’re certainly not dressed properly for the occasion. Looking presentable is important whether it’s for work or social occasions so here are some tips on what to wear when you want to look professional and fashionable in a business casual setting for the winter months.
Table of Contents
- 1. White Turtlenecks, Neutral Trench Coats, White Jeans, and White Boots
- 2. Tight T-shirts, calf-length Coats, Tailored Pants, and Ankle Strap Shoes
- 3. Black Sweater with Light Blue Jeans and Slingbacks
- 4. White Turtlenecks, Wine Red Trench Coats, Plaid Mini Skirts, and Over-the-knee Boots
- 5. White Tie-neck Shirts, Black Pencil Mini Skirts, Tweed Coats, and Over-the-knee Boots
- 6. White Tight Turtlenecks with Wine Red Bib Skirts and Over-the-knee Boots
- 7. Tweed Dresses in Leather Belt and Over-the-knee Boots
- 8. Neutral Sweater over White Shirts with Leggings and Leather Shoes
- 9. Sweaters, Calf-length Coats with Leather Leggings, and Ankle Boots
- 10. Black Tight Turtlenecks with Wide-leg Pants and Ankle Heel Boots
- 11. Wool Tops with the Wide-leg Vertical Plaid Jumpsuit and Ankle Heel Boots
- 12. V-neck Blouses, Plaid Pencil Skirts with Tights, and Ankle Strap Heels
- 13. Shirt Collar Sweater, Leather Skirts with Tights, and Knee-high Boots
- 14. Black Shift Dresses with Tights and Ankle Boots
- 15. Loose Sweaters with Floral Midi Skirts and Suede Heel Boots
- 16. Floral Cut Out Sweaters with Tailored Pants and Metallic Ankle Strap Shoes
- 17. Brown Turtleneck with Cream Pleated Midi Skirts and Flats
- 18. High-neck Sweater Dresses and Ankle Boots
- 19. Two-piece Set Sweater Dress and Ankle Boots
- 20. Cable-knit V-neck Sweater Vest with White Shirts, Neutral Pants, and Sneakers
- 21. Turtleneck with Dress Pants and Leather Shoes
- 22. Shirt with a Cardigan, Dark Jeans, and Sneakers
- 23. Sweater with Fleece Jackets, Dark Jeans, and Suede Shoes
- 24. Felt Jackets, White T-shirts, Jeans, and Sneakers
- 25. Sweaters, Plaid Knee-length Coats, Chinos Pants, and Sneakers
- 26. Hoodie with Knee-length Coats, Dark Jeans, and Sneakers
- 27. Turtlenecks, Suede Jackets, Dark Jeans, and Suede Ankle Boots
- 28. Gray Turtleneck, Moss Green Khaki Jackets, Black Trousers, and Leather Shoes
- 29. Sweater over Shirt with Jeans and Leather Shoes
- 30. Sweaters with Plaid Trousers and Sneakers with Beanie Hats
1. White Turtlenecks, Neutral Trench Coats, White Jeans, and White Boots
Looking classy and refined is essential for a business casual winter outfit. You need to wear a well-fitting turtleneck and white jeans, of course, but what’s more important is the outer layer. For this reason, you should choose an outfit that will have a neutral color palette with a modest amount of embellishments, such as a double-breasted jacket or faux leather vest. Most of the time, you should stick with simple straight cuts and not opt for anything crazy or trendy like the tried-and-true trench coat.

2. Tight T-shirts, calf-length Coats, Tailored Pants, and Ankle Strap Shoes
This looks easy to pull off in the winter but hard to get away from within the warmer months. However, don’t ever underestimate the power of a tight t-shirt. It can be combined with a pair of tailored pants, ankle strap shoes, and a calf-length coat which is great for a winter business casual look. This combination will make you look sleeker, and your package will appear smaller, so it’s recommended as one of the go-to business casual winter outfits.

3. Black Sweater with Light Blue Jeans and Slingbacks
This outfit is likely to be a favorite among those who love to dress up casual business styles. However, there’s a caveat because this is not the time to throw on some outlandish or trendy items. The black sweater needs to be fitted and elegant, so you need an item that’s not too wide or overly bulky. In addition, jeans should have a higher rise and be flat-fronted for your waist to appear smaller and your behind to look hairier than it is. The combination with light blue jeans is amazing. Lastly, slingbacks are appropriate for those who want a more casual look with their outfits.

4. White Turtlenecks, Wine Red Trench Coats, Plaid Mini Skirts, and Over-the-knee Boots
There is no need to be afraid of getting creative regarding what you wear in the winter. You will want to take advantage of the different shades of red, burgundy, and wine because these colors are becoming popular within the fashion industry. There is nothing wrong with mixing things up to have an unusual look without following trends too closely. Especially the combination with over-the-knee boots.

5. White Tie-neck Shirts, Black Pencil Mini Skirts, Tweed Coats, and Over-the-knee Boots
If you’re someone who likes to dress up and look more casual, then you should probably opt for a white tie-neck shirt. It’s a classic look that looks composed and is an excellent choice for those who want to be classy and sophisticated in their business casual winter outfit. Along with a great pencil skirts will do the trick, as a belt can be used to carry your outfit together. For example, heels will make your legs look good, but the over-the-knee boots are an excellent way of making the legs appear slimmer by lengthening them.

6. White Tight Turtlenecks with Wine Red Bib Skirts and Over-the-knee Boots
This is perhaps a slightly casual look that will bring out the best features of your outfit by making them appear fashionable and sophisticated. This is a great combination; nevertheless, the over-the-knee boots are a definite drawcard. The wine red bib mini skirt will add some color to your outfit, while your white turtleneck and boots make it appear classy and professional. Lastly, the tuck in the waist will add additional sophistication to your look.

7. Tweed Dresses in Leather Belt and Over-the-knee Boots
If you like to be casual, this is a great outfit for you. You can opt for a tweed dress and a leather belt to help make your outfit appear more classy and feminine. Additionally, over-the-knee boots are what you need on top of the tweed dress because they will give your legs some oomph by lengthening them. Lastly, this look is most recommended for those who love the fashion industry but don’t want to invest too much money into their winter business casual outfits.

8. Neutral Sweater over White Shirts with Leggings and Leather Shoes
This is a classic look that’s perfect for the winter. The neutral color in the sweater matches well with other neutral colors, while the leggings and shoes make you look presentable yet casual. Wear black or a smart gray blazer to go over this outfit, or pair it with a classy suit for an evening look. Remember that these are not your everyday clothes — you need to dress up to be presentable, which means looking more dressed up than your plain white T-shirts and dark jeans might suggest.

9. Sweaters, Calf-length Coats with Leather Leggings, and Ankle Boots
In a chilly environment, it’s vital to wear things that will keep you warm enough to function. You don’t want to be shivering throughout the day, so layers are your best friend. Several great items can be layered together for warmth. For instance, try a sweater under a long coat, pair of your favorite shoes with leather pants inside of the sweater, and some leather ankle boots over the leggings.

10. Black Tight Turtlenecks with Wide-leg Pants and Ankle Heel Boots
Fashion week is over, and the weather outside has gotten cold. You’re ready to get back into business casual wear, but you’re not sure which way to turn. The answer is simple: wear a black turtleneck with wide-leg pants and ankle-height boots. Not only will you look formal, but you’ll also have extra warmth from your layers.
Another classic look is perfect for the winter while appearing sophisticated and putting together. The black turtleneck with wide-leg pants is a nice way to wear your outfit because it will cover your neck if the wind picks up. Also, you may pair it with an ankle heel boot to make sure everything stays in its place.

11. Wool Tops with the Wide-leg Vertical Plaid Jumpsuit and Ankle Heel Boots
For the most part, you want to stick with smooth, comfortable materials and while a wool suit might be a little too formal for business casual, a simple wool top is perfect. Style it with a pair of wide-leg pants and tall boots to keep your legs warm without sacrificing style.

12. V-neck Blouses, Plaid Pencil Skirts with Tights, and Ankle Strap Heels
Sweet! You’ve found a knockout outfit that will make heads turn. This business casual outfit combines style, comfort, and warmth with the right balance of formality. You’ll look fabulous and very fashionable while also appearing sophisticated and professional.
The black pencil skirt should cover all of your bases, while the combination of the V-neck blouse and ankle strap heels makes this outfit one to be reckoned with. Don’t forget to add an elegant scarf or necklace around your neck, as well as some tights and ankle-strap heels. The combination of any skirt with tights is professional.

13. Shirt Collar Sweater, Leather Skirts with Tights, and Knee-high Boots
The next time you go to the office, try wearing a shirt collar sweater and leather skirts with tights and knee-high boots. You might not be comfortable in this outfit, but it’s guaranteed not to embarrass you in front of your boss. Lastly, the knee-high boots will add elegance and class to your look while keeping you warm. The combination of formality and comfort is exactly what you need for a professional setting, so why not try it?

14. Black Shift Dresses with Tights and Ankle Boots
While neutral colors are always a safe option for women’s winter business casual outfits, it’s not always necessary. If you’re looking for something more chic and sophisticated without coming off as too traditional, try wearing a black shift dress with tights and ankle boots. Again, it’s important to accentuate your clothing with stylish accessories but avoid any frills or bold colors that will take away from the elegant look of your ensemble.

15. Loose Sweaters with Floral Midi Skirts and Suede Heel Boots
The most important thing about winter business casual outfits is that they make you feel comfortable. You don’t want to go out in the cold wearing something you’re not used to wearing. If so, then it’s a great outfit for you! You’ll need two pieces to achieve this look: a flowery, midi-length dress and a simple heel boot. The dress can be any color that suits your style, but the skirt should be an earthy tone like black or blue. It doesn’t matter if the woman has a figure like a runway model — a loose sweater looks great on almost anyone. Wear your sweater with a midi on-trend skirt, and add some suede heel boots to complete your look.

16. Floral Cut Out Sweaters with Tailored Pants and Metallic Ankle Strap Shoes
It’s always important to put in the right amount of effort and look your best on a workday. However, certain outfits can be too casual, while others are too dressy. These outfits are comfortable and stylish but conservative enough for the office. You can never go wrong with a classic combination like this one. Floral cut-out sweaters paired with tailored pants and metallic ankle strap shoes look fantastic for winter business casual looks. You’ll be sure to make a lasting impression at the office or wherever you decide to wear them.

17. Brown Turtleneck with Cream Pleated Midi Skirts and Flats
You want to look your best on a workday, but you don’t want to overdo it. This is the perfect outfit for you. Don’t wear a dark-colored turtleneck; keep it light and neutral. There are no black-and-white stripes, but it still looks classy and sophisticated. It’s conservative, but not too much so when paired with cream pleated midi skirts and flats. You’ll look stylish and professional, but you’ll also feel comfortable. This winter business casual outfit is sure to keep you happy during the workday. There are many different types of flats, don’t forget to choose a pair for yourself.

18. High-neck Sweater Dresses and Ankle Boots
There are many variations of sweater dresses, but one thing that’s generally true about most sweater dresses is that they’re made from very warm materials. So if you want to put together a business casual winter outfit that combines formality with warmth, it’s best to choose a dress with a high neckline and long sleeves. Once you’ve chosen the dress, make sure to pair it with boots that go up to your ankle – or even higher – so your legs stay covered and warm.

19. Two-piece Set Sweater Dress and Ankle Boots
A two-piece set sweater dress and ankle boots are great winter business casual outfits to wear at work. The two-piece sweater dress is very warm and comfy. It’s nice that you won’t have to layer as many pieces of clothing as the dress will be heavy on its own. This business casual look also includes booties that go up to your ankles, which is crucial for keeping your legs warm during those extremely chilly winter days. Make sure your sweater has a high neckline and long sleeves because that’s what makes it a lot warmer than sweaters with low-cut necklines and short sleeves. Outfits with ankle boots, why not?

20. Cable-knit V-neck Sweater Vest with White Shirts, Neutral Pants, and Sneakers
V-neck sweater vests are the perfect solution for wearing when you want to look put-together and stylish but not too formal or too casual. Achieve the ultimate laid-back winter business casual look with a V-neck sweater vest, a cable knit sweater, and a pair of sneakers. Make sure that the pair of pants you choose is not too tight and looks good with your shoes.

21. Turtleneck with Dress Pants and Leather Shoes
When choosing a business casual winter outfit, you want to look minimal and elegant. That’s why it’s less important to wear flashy, trendy designs that show off your wealth than it is to wear something that will be clean looking on the outside and classy enough to wear in professional settings.
You can get away with wearing some turtlenecks, but nothing too thick or bulky. Instead, try pairing them with blazer-like jackets and slim-fitting dress pants. For a little bit of color, you can pair the ensemble with some black boots or leather shoes instead of relying on the gray ones all winter long.

22. Shirt with a Cardigan, Dark Jeans, and Sneakers
In a business casual winter outfit, you don’t want to wear something incredibly fashionable or anything that shows your wealth. Instead, you need to keep it simple and classic. There is a lot of room for play when putting together a business casual winter outfit. If you have the right kind of shirt, you can layer a cardigan over it and pair it with jeans – or dress pants as long as they are dark in color. While there are many types of sneakers, you’re sure to find the right pair for this combination. Add some sneakers to complete your look, and then you’re ready to go.

23. Sweater with Fleece Jackets, Dark Jeans, and Suede Shoes
You don’t want to be wearing a puffy jacket but instead a fleece jacket with a neutral color that will add some warmth to your outfit and still allow you to wear it in the office. Your best bet is to invest in men’s sweaters with neutral colors like creamy or brown. These colors are relatively warm compared to white and can work well in more casual environments. Stick with neutrals and earth tones, especially in the winter when almost everything is white or gray. For example, you can pair a scarf with your black sweater and add some suede boots for a versatile winter business casual outfit.

24. Felt Jackets, White T-shirts, Jeans, and Sneakers
When in doubt about what to wear when you want to look professional and stylish in a winter setting, go for something simple. The combination of a white t-shirt and jeans, and white sneakers is so popular because it’s so versatile. It can be worn on various occasions, from the office to social activities. In addition, you can add more style points by wearing plain black felt jackets instead of simple wool or leather ones.

25. Sweaters, Plaid Knee-length Coats, Chinos Pants, and Sneakers
For a winter outfit that’s both casual and warm, you need to keep the colors to a minimum and stick with neutral tones for the most part. You can use these colors as an accent piece, but if you wear too many loud colors, you’ll look out of place in a professional setting. For this reason, try pairing thick sweaters with chinos pants and some white sneakers.

26. Hoodie with Knee-length Coats, Dark Jeans, and Sneakers
The concept of this winter business casual outfit is to combine various styles. This means that you want to keep the color palette simple, stick with neutral tones, and avoid wearing flashy trendy designs that make you look ridiculous in public. However, wearing a hoodie is an important element of this outfit because it can be worn casually but still look respectable enough to wear in a professional setting. Furthermore, if you choose a hoodie with high-quality construction, it will also be comfortable enough to wear on the job.

27. Turtlenecks, Suede Jackets, Dark Jeans, and Suede Ankle Boots
For the more daring winter business casual dresser, you can throw on a suede jacket or scarf and pair it with dark denim jeans and suede ankle boots. It’s all about finding out what works for you, so if a turtleneck feels like it’s choking you, try something with a little less material. Of course, the best way to complete this outfit is by wearing suede ankle boots so that you’re ready for whatever winter throws at you.

28. Gray Turtleneck, Moss Green Khaki Jackets, Black Trousers, and Leather Shoes
The khaki jacket is not just a winter staple. You’ll be able to wear it during the spring and summer as well. However, khaki jackets and other neutral-colored pieces are more important during the winter and can help you look pulled together without adding too much bulk to your outfit. Leather shoes are a great pick when you’re aiming for a classic business casual look that’s sophisticated and minimal. Keep your pants black and your sweater gray or any other neutral color if you’d prefer white or brown.

29. Sweater over Shirt with Jeans and Leather Shoes
Winter is cold, so your business casual winter outfit must reflect that. Pick a sweater over a button-down shirt and pair it with slim jeans for a cleaner look than wearing your winter coat all the time. Try pairing it with black boots or leather shoes to make the appearance seem more professional, though you can get away with brown loafers if you want to be on-trend.

30. Sweaters with Plaid Trousers and Sneakers with Beanie Hats
As with the previous outfits, the main goal of a business casual winter outfit is to have something clean and simple on the outside and have some sweetness to it. You don’t have to go all out with a scarf or coat. Just wear a sweater that’s thick enough so you can still see your skin on the outside and pair it with neutral plaid trousers and white sneakers for a look that will work in any environment.
