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11 Winter Must-Haves For Men

Bundle Up with These Winter Essentials!

When the cold winds of winter blow, the Classic satorialist savors the season, because lower temperatures invite both the need and the opportunity to layer outerwear, clothes, and accessories to create insulating, and incredible, ensembles.

A vast array of garments and articles, including sweaters, boots, vests, overcoats, topcoats, gloves, scarves, and more come out of the closet, presenting countless opportunities to combine all of these components to a degree that would not be feasible during the warmer months of summer or spring.

A portrait of William Shakespeare

“How like a winter hath my absence been from thee, the pleasure of the fleeting year! What freezings have I felt, what dark days seen! What old December’s bareness everywhere!”

William Shakespeare

In today’s guide, we will highlight 11 items that we believe deserve a place in the wardrobe of any Classic Style enthusiast and are winter wardrobe essentials. Versatile, elegant, and, above all, warm, these garments and accessories are sure to elevate all of your hibernal habiliments.

Get inspired by our Winter Lookbook!

1. Insulated Boots

Contrary to what you might assume, well-insulated boots that keep your feet warm don’t have to appear rugged and utilitarian, like the famous duck boots manufactured by L.L. Bean. Some models of classic men’s dress boots can be found with the addition of lining, ideally of sheepskin or fleece, that warms your feet without spoiling the dapper and elegant lines of the footwear. 

Unfortunately, these boots have become increasingly rare as more and more makers only line their boots with leather; this practice is typical in Italy and even in the colder climes of England. However, with a little work, you can locate a pair that serves your needs and that will certainly be worth the investment when the temperature drops but you don’t want to sacrifice the style of your footwear. 

Are L.L. Bean boots worth their price?

2. Casual Warm Jacket

Photo of a quilted jacket
Raphael favors casual warm jackets with interesting patterns, like the houndstooth on this quilted jacket. 

While an overcoat is a favorite option for staying warm in winter, you will also require a more casual, but no less insulating, jacket to wear on less formal occasions. Jackets of this style will have a considerably shorter hem than an overcoat, falling to around the mid-thigh or slightly lower. Shorter jackets that reach only to the waist are unlikely to provide sufficient warmth. 

Ideally, you should seek out a jacket made from a heavy and thick fabric: it will last longer, drape better, and keep you warmer. If your local climate justifies it, the addition of another layer of lining may be helpful.

Which jacket is right for you?

The peacoat traditionally features slanted pockets

Peacoat

Versatile and elegant option with a flattering and masculine silhouette.

Raphael wearing green duffle coat

Duffle Coat

Exceptional option for colder weather thanks to its large, insulating hood.

Raphael in his houndstooth-patterned Barbour quilted jacket

Quilted Jacket

Wool will be warmer than polyester-filled models.

3. Classic Hats

Because of its size, we lose a considerable amount of heat from the tops of our heads. Hats help to trap that heat, keeping us warm, and classic hats help to keep us looking refined and elegant no matter how cold it gets.

Therefore, there is no need to settle for a beanie or oversized snow hats with ear flaps: in almost all conditions, a classic hat will keep you just as warm while appearing far more dashing. For a more casual and utilitarian look, consider a flat cap, and, of course, the timeless fedora is never out of season. 

Learn how to confidently wear your hat!

4. Colorful Lined Gloves

Gray Gloves combined
Refined day gloves have always been a mark of a gentleman.

For centuries, a gentleman wasn’t fully dressed without a pair of elegant day gloves, but during the winter, he would switch out his unlined gloves for a more insulating pair usually lined with cashmere or wool. As an extremity, your hands are one of the first parts of your body to get chilly in wintertime, and protecting them with a quality pair of gloves is essential. 

Esquire May 1938 - Multiple Paired Stripes

Classic Gloves were

Colorful!

While most men today wear black and brown gloves, colorful gloves were the norm during the Golden Age of Menswear. Colorful gloves were favored because in addition to adding unexpected visual interest, they could be paired or harmonized with other aspects or accessories in the outfit, creating a more cohesive sartorial whole. Nowadays, as colorful gloves have become more rare, they are an exceptional way to stand out from the crowd in a subtle but sensational way.

Fort Belvedere has a pair of gloves for you!

Do you know the hallmarks of a quality glove?

5. Textured Overcoat

In addition to the aforementioned casual jacket, your winter wardrobe would not be completely without a classic overcoat, which is a superior option to a bulky puffer coat or parka.

Most men today wear plain overcoats in a solid and relatively bland color like black, charcoal, or navy. While perfectly correct, such overcoats limit your styling potential and can make your winter apparel seem drab. 

Illustrations of 1930s overcoats
Classic overcoats came in many colors, textures, and patterns.

Selecting an overcoat with a pattern, such as herringbone or houndstooth, or a combination of different tones, will offer more opportunities for setting off the other aspects of your ensemble and appear more visually stimulating. Such overcoats are perfectly suitable for both formal and information occasions and can be worn for business or pleasure. A wool overcoat will be particuarly insulating.

Having the right accessories can really upgrade an entire outfit no matter the season

Here’s why Raphael loves

Tweed

Especially for his brown overcoats, Raphael favors a tweed weave in bold patterns, such as Donegal tweed with its different flecks of color. The variety of colors can pick out any other colors in your ensemble, making this overcoat easy to pair while remaining exceptionally unique.

Learn to pair overcoats with scarves and gloves!

6. Dinner Jacket

Photo of two men one in a tartan dinner jacket one in velvet dinner jacket
Dinner jackets are available in unique patterns, like tartan, or textures, like velvet.

During the holiday season, especially around Christmas and the New Year, there tends to be so many formal evening parties that this period is sometimes referred to as “Black Tie Season.” If you regularly attend fetes of this formality, you might become a little bored with your traditional tuxedo

Liven things up, and embrace the festive spirit, with a velvet dinner jacket. Available in a wider array of colors, including midnight blue, bottle green, burgundy red, gray, and even lilac, these dinner jackets ensure a holly jolly time and can be paired with other merriment-inducing accessories, like colorful socks, bow ties, and cummerbunds, plush evening slippers, and unexpected patterns like tartan. 

Colorful Silk Formal Evening Socks from Fort Belvedere

The Perfect Companion to any Colorful Dinner Jacket

Want to learn more about Festive Formalwear?

7. Sweater Vest

Raphael wearing a classic blue graph check shirt
Raphael wearing a classic blue graph check shirt with alpaca sweater vest.

Colorful attire at your midsection is sure to make a splash on a gray winter day, and you can achieve that color without sacrificing warmth by wearing a sweater vest, also known as a sleeveless jumper. 

This garment is similar to a vest in that it has no sleeves and to a sweater because it is knitted. These features allow the garment to be very flexible, warm, and versatile: it can be worn in a wide variety of ways. 

Sweater vests appear elegant under outerwear like a pea coat, with a suit, under a sport coat or blazer, or on its own with a button-up shirt, either a dress shirt or a flannel shirt. They add warmth without adding bulk and won’t spoil the lines of your other garments.

Leather jacket & sweater vest

If you are wearing neckwear …

Wear a V-Neck!

If you wear neckwear such as a tie or a bow tie, we suggest that you wear a sweater vest with a v-neck. This opening will put your neckwear on full display for all to enjoy. It will also ensure that the knot of your tie does not create an odd bulge under the fabric of your sweater vest. This advice also applies to other types of sweaters.

8. Seasonal Winter Ties

Accessories help your entire wardrobe go farther, and seasonal accessories ensure that you are able to adequately style your looks no matter the weather. In Classic Style, few accessories are more versatile and refined than neckties, and so it will behoove you to invest in a curated selection of seasonally-appropriate winter ties. 

Winter-weight materials are particular favorites for this sort of neckwear. Cashmere is very popular, as is wool because of the many ways it can be colored or woven with colors and patterns suitable for cold weather, such as a wool challis or beautifully textured wool grenadine

Alternatively, silk is a year-round fabric that appears beautiful in the winter. A madder silk is perfect for the season because it features muted earthy tones that are perfect for cool and cold weather.

Photo of Corduroy jacket worn with silk knit tie gray waistcoat earthone pocket square details shot

Raphael Recommends:

Knit Ties

Knit ties in silk or wool are a cool and cold weather favorite for Raphael because they have a unique crunchy texture that is more casual than traditional ties while still appearing elevated and unique. 

Do you own these five essential ties?

 

9. Dressing Gown

Illustration of Men in a dressing room admiring dressing gowns robes smoking jackets
Historical dressing gowns could be very colorful and dramatic.

When it’s cold outside, it’s likely also colder inside your house. Therefore, adding additional layers and adding a dressing gown dressing gown to your wardrobe is perfect because you can comfortably lounge all the while feeling very warm.

Dressing gowns are available in a wide array of materials, including silk, cotton, velvet, and wool, with weights to suit your local climate. They also come in any desired color or pattern, but fanciful designs in rich and deep colors were typical during the Golden Age of Menswear.

Unlike a bathrobe, a dressing gown is meant to be worn on top of clothes: it has a roomier cut and a heavy drape to lie beautifully over other garments. With vintage charm and Old World appeal, a dressing gown is sure to be a beloved addition to your wardrobe.

Photo of a bath robe

A Dressing Gown is not a

Bathrobe

Unlike a dressing gown, a bathrobe is not meant to be worn over clothes. Instead, it is usually worn as part of bathing or while at the spa or pool. As such, it is commonly made from a lighter, water-safe material like cotton terry cloth that is not as refined as that of a dressing gown.

Do we wear dressing gowns at home?

10. Heavy Knit Sweater

Few garments are as elegant, or as insulating, as a beautifully-knit sweater or cardigan. With its athletic lines and figure-improving compression, a sweater is an essential cold-weather garment that can also be worn during transitional seasons, providing simple layering opportunities along with effortless style.

Ideally, you should avoid cotton as a material because it is lightweight and breathable and therefore won’t trap heat well. Wool sweaters, alpaca sweaters, cashmere sweaters, or blends are all superior options. In warmer climes, lightweight knitwear like a turtleneck may be a preferable alternative.

11. Gold Accessories

Monkey Fist Knot Cufflinks in Gold by Fort Belvedere
Gold-toned jewelry is especially suited to cool and cold seasons.

You may not have known that lusters can be seasonal, but the fact of the matter is, gold tends to have a much warmer tone than silver and as such is very appropriate for cool and cold weather. In frigid temperatures, the tawny glint of yellow gold will put you in mind of the blazing sun, while rose gold resembles the crackling embers of a merry fire. 

Gold also emphasizes the seasonal color palette of the cold and cool months, setting off beautiful deep dark reds, inky blues, rich browns, and similar earth tones. No matter how it is worn, gold adds warmth to your winter outfits. 

Timeless Gold Jewelry from Fort Belvedere

Want to learn more about men’s jewelry?

FAQ

What are the must-have winter essentials for a classic menswear wardrobe?  

A well-equipped winter menswear wardrobe should include a tailored overcoat, a high-quality wool suit, a selection of turtlenecks and crew neck sweaters, a durable pair of leather boots, a classic scarf, gloves, and a versatile hat such as a flat cap or fedora.

How do I choose the right overcoat for my style? When selecting an overcoat, consider the garment’s length, material, and color. A classic fit that allows layering, made from wool or cashmere in classic colors like gray, navy, brown, or camel, usually complements most styles.

Can I wear sneakers with classic menswear during winter?  

While traditional winter classic menswear typically pairs with dress shoes or boots, modern style allows for clean, minimalist sneakers in leather or other premium materials, especially for a smart casual look involving jeans.

What types of sweaters work best for layering?  

For layering purposes, merino wool or cashmere sweaters in crew neck or turtleneck styles work excellently. They provide warmth without excessive bulk and can easily be worn under suits or jackets.

What are some tips for maintaining leather boots in winter?  

To maintain your leather boots, regularly clean off any salt or snow, condition them to prevent drying and cracking, and waterproof them to protect against moisture. Also, consider using cedar shoe trees to retain their shape.

Is there a stylish way to keep my hands warm without compromising dexterity?  Yes, opt for high-quality leather gloves that are fitted but not tight, which allow for both warmth and hand mobility. For added functionality, look for gloves with touchscreen compatibility that are water resistant.

What kind of hat is appropriate for classic menswear in winter?  

A wool fedora or trilby can add sophistication to a classic ensemble, while a cashmere or wool flat cap provides a more relaxed yet refined option suitable for most occasions.

How do I add color to winter ensembles?

Accessories are the simplest way to add color to any winter ensemble. This way, you can source foundational items, like an overcoat, in a more universal color and create visual interest with other items.

Conclusion

Raphael walking in the snow wearing a thick overcoat.
No matter how cold it may get, you will have these 11 essential winter items to help keep you warm!

When the weather outside is frightful, we hope that you will find this list of 11 must-haves for winter menswear insightful! Cold weather provides countless opportunities for unique and exciting ensembles, and armed with the items suggested in this list, you are now prepared to craft outfits that are sure to take the chill out of the season!

Let us know in the comments, what items appear on your list of winter essentials? 

Herringbone Cashmere Scarf in Mustard Yellow and Grey

Fort Belvedere

Herringbone Cashmere Scarf in Mustard Yellow and Gray

www.gentlemansgazette.com

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