Modern Gentleman

How to Style the Best Winter Menswear for Any Occasion

As a new year beckons and as frigid winter weather sweeps most of the country, reflections abound: New resolutions, a new outlook on the world, new goals in the office and on the road. Greater horizons – and even simple matters about town – call for the right approach, and the right menswear to guide you along the path at hand.

Philosophical though it might seem, the adage comes down to putting your best foot forward, and letting your wardrobe help lead the way, at least in sartorial matters. The best winter style essentials can work in harmony, helping you tackle any number of situations with confidence and the right mindset: If your capsule menswear wardrobe is a toolbox, then it should be well-stocked and at the ready. 

And even the best winter fashion for men requires some tweaking, or diving a level deeper. The capsule wardrobe comes to a head again as you explore a personal favorite of ours, the 3-Layer Rule, packed with plenty of tips for styling the season’s finest.

The idea of working smarter, with efficiency and quality in mind, should also stay at the forefront as you scour your closet – naturally, Anatoly & Sons menswear aims to provide a helping hand with the finest fabrics, exceptional construction across everything from tailoring to shirting, and the right finishing touches.

But even the most carefully crafted winter coat or pair of trousers feels aimless without a winter style guide. Consider the basic building blocks of a stylish winter menswear look, like a proper overcoat, the right sweater and a crisp shirt. These are among the pieces we’ll explore today as we talk about how to style winter menswear for (almost) any occasion. 

Dress to Impress – From the Jump

In brisk and blustery winter weather, matters of form and function take heed – oftentimes, your best defense starts on the outside as far as seasonal squalls are concerned, and a stylish, classic men’s winter coat is a Swiss Army Knife of sorts. 

Particularly when cut in a length that’s both long enough to cover the upper thigh as well as a blazer, field jacket or suit jacket, an iconic style like the Mac Coat is a proper selection for situations both more easygoing and more formal. 

The Anatoly & Sons Navy Mariner Mac Coat delivers as far as form is concerned, with a crisp navy color made to match with nearly anything in your wardrobe, plus a classic single-breasted button front and a large collar made to be turned up against the wind.

And in matters of function, 100 percent wool flannel construction will prove weather-ready in the wind and snow. Our Mariner Mac Coat goes so far as to feature a removable interior vest and five total pockets for your everyday essentials, plus a single vent for ease of movement. It makes a statement without veering too bold, and much could be said for the layers it helps to shield, including our Anatoly & Sons Grey Merino Quarter-Zip and an appropriately paired Olive Stripe Cotton Dress Shirt.

Overcoat Blue VBC

The Art of Layering In Style

Beneath your winter coat, the next step in impressing – from a dinner party crowd to the office – comes in moving with quiet confidence. A crisp grey quarter-zip sweater like our Anatoly & Sons Grey Merino Quarter-Zip  wears well with any color and virtually any sport shirt, including the  Olive Stripe Cotton Dress Shirt beneath. 

A tie can be added to this look with ease, while the merino wool fabric keeps you cool under pressure (and warm when you need it). It’s these two pieces that offer a springboard for elegant-yet-versatile dressing alongside the Charcoal Cavalry Twill Trousers, a prized favorite boasting exceptional fabrication and utterly classic good looks. 

The clean drape of these pants rests easily atop leather Oxford shoes, leather dress boots or a personal Anatoly& Sons favorite, sleek Brown Suede Chelsea Boots – or perhaps leather sneakers based on the conditions on the ground and the climate at large. 

Depending on the situation, a sportcoat could be swapped for your quarter-zip sweater, but handsome charcoal wool trousers lend refined appeal to this ever-wearable winter look. 

Merino Wool Quarter Zip

Stepping into the Winter Season

Between their supportive appeal, clean silhouette and effortlessly stylish good looks, the Chelsea boot is both a menswear classic and a tasteful modern essential. While our Brown Suede Chelsea Boots require extra care in the winter based on your locale, they deliver a mix of rakish style and an eye-catching contrast to charcoal trousers.

A pair of Dark Brown Medallion Cap-Toe Oxford from our Anatoly & Sons line, on the other hand, portray classic confidence and office-ready style. Your menswear toolbox or capsule wardrobe is well-equipped from the top down and the ground up. This winter look gains an extra ounce of attention to detail through precisely selected Wool-Nylon Socks, made to pair easily with the colors on hand here. 

Your choice of a dashing winter hat from our Anatoly & Sons selection can also serve as a knowledgeable sartorial statement: A newsboy cap proves practical in keeping the wind and rain out of your eyes, and delivers traditional good looks in a neutral shade of light grey or tan houndstooth.