Now that you’ve survived the heat of summer (and the frustration of navigating summer fashion!), it’s time to embrace cooler months. Winter men’s business casual is the ideal avenue for updating your wardrobe. Fall and winter offer the chance to play with layers and textures, meaning it’s way easier to look put together.
If you’re unsure how to start gearing up for this change of season, you’ve come to the right place. As experienced stylists who have worked with CEOs, executives, and entrepreneurs of all fields and ages, we’ve got you covered. We’ll walk you through our simple style system, which will make getting dressed each morning a breeze.
Then, we’ll show you the three staples you need for a men’s business casual winter wardrobe and styling tips. So long summer! Let’s jump into the end-of-year vibes.
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The Easy Executive Workwear Style System Every Guy Needs
Great style is easy if you have the right strategy and pieces in your closet.
Next Level Wardrobe’s patented Style System empowers professional men to build confident, impactful office looks. Say goodbye to shopping mall stress and wardrobe confusion. We simplify it with three key steps: essentials, core colors, and fit.
1. Focus on Essentials
Invest in classic pieces that match your lifestyle and professional goals. These pieces will be the backbone of your closet. With a minimalist wardrobe filled with high-quality essentials, you can make more outfits with less stuff.
Often, men struggle with casual workwear (and really any work clothes) because they lack the right building blocks. Here, you should make a list of the pieces you actually need.
What is your work dress code? Do you need casual workwear? Men’s formal wear? How about what pieces do you wear every week? What is your closet lacking? Dig into these questions to find out what your essentials are. Once you have that, invest in high-quality items, but don’t overbuy! Just get what you need.
2. Focus on Core Colors
Next, prioritize what we call core colors, which are black, white, navy blue, and gray. These neutral shades go with everything. You can wear them with each other or even bright pops of color. That’s why these colors should make up the largest percentage of your wardrobe: they’re easy to mix and match.
Once you have that foundation, you can add more colors. Make the second-largest portion of your wardrobe dedicated to tonal colors—aka, other neutrals, along with shades and tints of the original core colors. This is also a great opportunity to mix in texture.
Last, the smallest third of your clothing collection should be made up of bold prints and patterns. This allows these fun splashes of personality to act as just that: accents. They don’t overwhelm your closet, they’re the cherry on top.
3. Focus on Fit
You can have all the right colors and pieces, but if they don’t fit, your wardrobe is a bust. Seriously, if there’s one thing we cannot stress enough, it’s the importance of fit in your winter business casual wardrobe. Men’s clothing isn’t made with every male body in mind. In fact, designers typically use one “fit model” and pattern to make entire lines. So if your build doesn’t match up with that model, you’ll likely struggle with fit.
Guys often have width issues around their shoulders and thighs. Other common areas are the pant hem and stomach. Do any of these fit challenges sound like you? Then it might be worth consulting a tailor.
We know, we know, alterations sound like an extra expense. But, alterations are common and can save you money in the long run. Start by asking a well-reviewed tailor to hem a pair of trousers or work pants. Getting that perfect break can take you from schlubby to polished in a snap.
3 Winter Men’s Business Casual Closet Must-Haves (And How to Style Them)
Feeling less stressed about how to start building your dream closet? Good. Let’s get into the business casual pieces men need this winter. Our three essentials are:
- Cashmere polo shirt
- Leather lace-up boots
- Cotton corduroy trousers
Keep scrolling to find out why these items keep you stylish this season and how to build outfits with them.
1. Cashmere Polo Shirt
Product by Mr. P, shop here.
Ready to dress business casual? Men, winter is coming, which means cashmere season has officially arrived. We love cashmere because it’s cozy without being stuffy and soft while still lasting for years to come.
While a cashmere crewneck is always a classic, these days, we recommend trying out a polo cut. As professional stylists, we hardly ever see this silhouette in men’s closets. But we’d say it’s a must because it’s the right balance of formal and casual (Dare we say, power casual?) The collar gives off a professional air without seeming overdressed. And, the soft knit makes it more approachable and modern.
Basically, it says, “I’m cool, but I’m not trying too hard.”
If you have an athletic body type, this is a great way to show off your muscles without going overboard. It’ll hug your body while still being work-appropriate.
Style this for the winter with darker pants, leather boots (more on that later), and a luxe overcoat. If it’s not quite cold enough, trade your overcoat for a lightweight suede bomber jacket.
2. Leather Lace Up Boots
Product by Mr. P, shop here.
In our opinion, fall and winter are the best seasons for dressing well. Part of that has to do with all the incredible leather (or like-leather) goods you can sport while being seasonal. Boots are no exception to this rule of business casual winter wear for men. This is the time to dust off your boots or invest in a quality pair like these from Mr. P.
We suggest this boot as essential because it’s well-made, has a core color, and is timeless. We especially love the color of tobacco brown because it feels more modern and approachable than black. They’re also practical, keeping your feet warm like no tech sneakers ever will.
(If you’re still wearing Allbirds, this is your sign to upgrade!)
Speaking of Hokas, let’s dispel a common misconception. Many guys think that the only way they can be comfortable is if they wear their trusty Hokas 24/7. Not true. Many styles of shoes (including these boots) are comfortable enough to wear all day.
You can easily wear these at work with trousers and a button-down and then transition them to nighttime with a sweater or jacket. No more having to change your whole outfit partway through the day.
3. Cotton Corduroy Trousers
Product by Nudie Jeans, shop here.
One thing to remember as you dress for the seasons is textures. Textures, whether the airiness of linen in summer or the coziness of knits in fall, subtly bring outfits to life and help you visually fit into that time of year.
Corduroy is a beautiful, rich-looking fabric with a strong point of view. The “wefts” in the fabric are what give corduroy its unique, touchable feel. The best part is that this fabric is equal parts durable and comfortable. So why not round out your smart casual workwear with a pair of men’s cords?
Like the other items on our list, this is perfect for any guy who wants to level up without looking like they’re trying too hard. The dark chocolate color fits the season, and the slim fit reads as polished.
Partner this with any core-colored top for a grade-A outfit, no matter your dress code.
Men, are you ready to elevate your business casual look this winter?
You don’t have to take on winter men’s business casual style alone. That’s what Next Level Wardrobe’s professional stylists and image consultants are for. Apply for our men’s styling services and see how we can transform your style into a streamlined, polished process.
