6 Men’s Winter Clothing Essentials

Winter clothing. Can you be practical, warm and stylish?

You want to keep warm but that shouldn't mean you have to sacrifice your style, right?

In this article, I'm going to show you 6 things you need to add to your wardrobe to keep stylish and warm this winter.


Without further ado, let's get into the 6 casual cold weather clothing essentials you need when the temperature drops.

1. Long-Sleeved Henley Shirt

Henley shirt (sometimes incorrectly referred to as ‘grandad collar shirts') were the traditional rowing uniform for those competing in the English Henley Royal Regatta.

Think of a Henley shirt as a t-shirt with a bit more character. The Henley is collarless and has a round neckline with a buttoned placket which is usually around 4 inches long. It's available in long and short sleeve – with the long-sleeve Henley shirt as our choice for winter.

henley shirt


In terms of formality, the Henley sits between a t-shirt and a polo shirt.

I know what you're thinking. How does the Henley shirt fall under ‘winter clothing'? The Henley shirt is perfect for winter layering. It makes a great base layer, onto which you can add cotton, flannel or denim shirts. For a great triple layered look (and extra warmth), you can add a sleeveless insulated coat on top of these two layers.

Keep your outer layers open to show off the Henley's buttoned placket and to draw attention to your chest.

You can also use the Henley shirt over a button-down shirt as a great casual alternative to wearing a sweater over a dress shirt.

Always remember the golden rule: get a good fit. To rock the Henley shirt, go for plain neutral colors and use the layers to add contrast and interest to your outfit.


2. Winter Clothing – Button-Down Shirt

winter clothing

The men's button-down shirt collar is attached to the shirt and often comes with large casual patterns, like the red checked shirt shown. It looks great when layered and unbuttoned over a Henley shirt.

The button-down shirt meaning can be confusing. The difference between button-up and button-down is this: a button-down shirt has buttons on the collar which fasten it to the shirt.

The button-down was originally worn by Polo players who became tired of their collars flapping up in their faces while riding and it's also worn by cowboys – presumably for the same reason. Its athletic pedigree makes the button-down a great casual alternative to the traditional men's dress shirt.

Men's button-down shirts have a soft collar made from casual, rugged materials like flannel and denim. Flannel in particular will keep you warm and stylish this winter when layered over a simple fitted white t-shirt or long-sleeved Henley shirt.

Layering a button-down shirt over a Henley shirt is a stylish winter look but remember to keep the top 3 or 4 buttons undone to show off the buttons on the Henley.

Stay warm and casual this winter by wearing your button-down under a sweater – letting the collar, sleeves, and bottom peak out.

Button-down fabrics are often patterned and come with pockets and epaulets. You wouldn't see these features on the traditional dress shirt and they add to the casual look.

Go for a looser fit but stay away from too baggy – your shirt should still be tapered at the sides. If your button-down has a flat bottom hem, you can wear it as an untucked shirt but make sure it doesn't fall any lower than the bottom of your back pocket. Any longer and you're veering dangerously into dress territory).


3. Hoodies For Men

winter clothing

Layer a hoodie under a flannel shirt or leather jacket for a stylish winter look.

The hoodie was introduced in the 1930s as a way to keep laborers from freezing in harsh conditions. It was popularized by Rocky and hip-hop culture.

There are no two ways about it – hoodies for men are casual, but worn in the right way, the hoodie looks as good as any casual sweater.

Your hoodie should fit snugly with no bagginess around the waist and it should never be any longer than the seat of your trousers.

Hoodies for men are available in a huge range of colors, fabrics, styles and patterns –  with and without logos. For the best look, go for simplicity – opt for a solid color and avoid visible branding. A zip-up style will give you a stylish, slim fitted look which is perfect for layering.

You can partner your hoodie with a leather jacket for a warm, comfortable and stylish look or you can wear it with a parka or pea coat for an urban, contemporary look.


4. The Man's Knitted Sweater

mens knitted sweater

Woolen knitwear is an essential component of any man's winter clothing wardrobe. Wool is the best material for warmth and is synonymous with winter clothing.

Sweaters with a texture like the chain or jacquard knit give your outfit visual interest and work well under an outer layer like the denim jacket. A sweater made using unscoured wool retains its natural oils which means it is water resistant and wearable when wet.

Remember that wool shrinks in the wash so you may want to go for a larger size.

If you want to dress up your sweater, go for a triple layered look and wear your knitted sweater over a dress shirt. For extra warmth, add a sports jacket made from a rugged fabric like tweed or herringbone.

Knitted sweaters should be fitted to your body and not baggy or tight. When making your purchase, you may want to go slightly bigger because wool shrinks a little in the wash.


5. Men's Dress Sneakers

dress sneakers

At one time, men's sneakers were unapologetic-ally casual but now you can buy dress sneakers designed to be worn with a suit, chinos, and jeans.

The finest men's dress sneakers use top quality dress shoe materials like calf leather. You can embrace the fall/winter look with suede but make sure it is water resistant (a waterproofing spray is essential).

Go for a minimalist design with a monochrome or subtle two-tone upper and minimal branding. Make your outfit pop with a bold neutral color – brightly colored sneakers risk clashing with your outfit and can look childish. You can't go far wrong with a pair of white, classic leather sneakers but black is a more practical color if you're walking in snow and slush.

The key is to avoid looking sloppy and of course to avoid the dreaded ‘dad sneakers'. A dad sneaker is chunky, usually has a logo and is synonymous with badly fitted faded jeans. These sneakers are acceptable in the gym but nowhere else and please – no Velcro straps. Ever!

You should choose a low top sneaker (showing the ankle) rather than the high top (covering the ankle). If you need ankle support when it is slippery underfoot, consider a casual ankle-high boot like the chukka boot.


6. Men's Leather Boots

winter clothing

The casual work boot has a sleek look and good grip – perfect for slippery conditions.

The work boot is a sturdy, practical lace-up leather boot originally designed for manual work. Work boots are perfect durable winter footwear.

Think of work boots as the Chelsea Boot's rugged cousin. They look great with dark slim fit indigo jeans and a knitted sweater.

Find a work boot with durable rubber soles that will grip the slippery winter terrain and keep you vertical. And feel smug as someone in Chelsea Boots glides by on the seat of their pants.

Water resistance is high on your priority list. Look for a Goodyear welt and full grain leather which will allow you to apply waterproofing treatments like dubbin wax to protect you from the elements.

If you have been out in wet conditions, stuff your boots with newspaper to soak up the moisture and allow them to dry out before wearing them again.

And there we have it. 6 winter clothing essentials will allow you to dress casually, stylishly and warmly this winter.