15 Men’s Winter Style Essentials Worth Picking Up Right Now12 min read

With fall soon behind us and winter on the horizon, you’ll want to be equipped with these winter essentials to help get you through.

15 Men's Winter Style Essentials: Menswear Pieces Worth Picking Up Right Now | GENTLEMAN WITHIN

Here’s what I consider men’s winter style essentials worth picking up right now. It’s a collection of some of my favorite pieces in menswear over the past few years. All inspiration is taken from my Gentleman Within Instagram account as well as my personal Insta.

Hit the play button below to watch the video featuring dozens of bonus winter looks. If you like it, be sure to hit the thumbs up!


WINTER STYLE ESSENTIALS for Men 2021 | Khoi's Curated Cold Weather Wardrobe Picks

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Let’s get right to it.

Thick layers/fabrics, textures, accessories and generally darker colors (black/gray). It’s smart to keep rich and deep colors around like plum, merlot, burgundy, and forest green around.

1) Go-To Pair of Boots

SHOP THE BOOTS—1) Thursday Boot Co. President Men’s 6” Lace-up Boot | 2) Thursday Boot Co. Captain Men’s 6″ Cap-Toe Boot | 3) Pikolinos Alpes Moc-Toe Men’s Boot | 4) Thursday Boot Co. Duke Men’s Chelsea Boot | 5) Clark’s Originals Men’s Desert Boot | 6) Wolverine 1000 Mile Boots | 7) Allen Edmonds Dalton Boot

A solid pair of go-to boots will get you through the fall and winter season in impeccable style. I recently put out a post on 7 awesome fall/winter boot styles for men. You’ve got endless options from a work boot to a dress boot, chukka to a chelsea or even a moc toe. Hard to go wrong with any of those. Take your pick.

SHOP THE BOOT—Thursday Boot Co. Captain Men’s 6″ Cap-Toe Boot

Me personally, this year I’m loving a pair of navy, suede boots. It’s ultra stylish, and the dark navy color still makes it very versatile and it’s just different from the sea of black and brown boots you’ll see out there.

2) Turtleneck Sweater

Turtleneck Under Suit Jacket Details
SHOP THIS LOOK—Suit: Indochino (similar) | Sweater: Banana Republic | Watch: Brathwait | Pocket Square: Brooklyn Wolf | Lapel Pin: Sprezzabox

The turtleneck (rollneck) sweater is one of those polarizing pieces. You either hate ’em or you love ’em. So how does one pull it off without channeling a Steve Jobs aesthetic? Simple, rock it with a well-fitting blazer and you’ll look like you know a thing or two about style. It’s that easy.

Feeling bold, try it with a double breasted suit jacket or you can pair the turtleneck with wool trousers and monkstraps for a stylish, elevated look.

3) Shawl Collar Cardigan Sweater

SHOP THIS LOOK—Flannel Shirt: Tailor Store | Cardigan: Asos (similar)

A chunky knit cardigan, otherwise known as the old man sweater. But don’t sweat it, these sweaters are staple fall and winter layering pieces. They’re prime to be worn under thicker outerwear. Or you can wear it overtop of lighter and mid-weight layers as a jacket. Their casual nature make it ideal to be worn with a button down shirt and necktie.

4) Warm Winter Coat

SHOP THIS LOOK—Coat: Sold Out | Trousers: Banana Republic | Boots: Thursday | Gloves: Elma | Scarf: Sold Out

SHOP THIS LOOK—Peacoat 1: Burberry (expensive) | Peacoat 2: Billy Reid (expensive) | Peacoat 3: H&M (budget) | Peacoat 4: Target Goodfellow & Co. (budget) | Peacoat 5: Forever 21 Men’s (budget)

This one is a given. Cold winters demand a warm winter coat. You’ll definitely want either a topcoat, peacoat or a parka depending on whichever style you like best. Of course you can’t go wrong with having all 3 in your arsenal. An additional item that is often overlooked is the car coat.

A parka is perfect for more casual outings, think jeans, heavy-weight henley and work boots. Whereas a topcoat or peacoat is more appropriate for dressier outfits, for example over top of a suit jacket.

Since my outerwear game is lacking a bit, I’m currently in the market for a quality, well-fitting wool topcoat so if anyone has any suggestions, I’m all ears.

Bonus Essential:

A lint roller can come in handy for anything wool. Since a roller is too big when you’re on-the-go, keep a small lint remover or brush in your coat pocket at all times.

5) Wool Trousers

SHOP THIS LOOK—Wool Trousers: Banana Republic | Shoes: Allen Edmonds | Watch: Stuhrling (similar) | Necktie: Sold Out

Wool is definitely a winter fabric. It’s my favorite type of fabric to wear in the cold. It not only keeps you warm, but is the perfect way to smarten up a more casual garment, for example a denim jacket. They can also be worn dressed down with sneakers for a smart casual look, and if you wanted to elevate things even further you can pair them with brown brogues, double monks or suede dress boots.

6) Woolen Tie or Knit Tie

If you’re looking to winterize your tie game, go for textures, particularly woolen or knit. Wool fabric and silk knit ties are ideal for winter. A woolen and knit tie’s texture is a great way to add visual interest to your winter getups.

There’s also a certain dullness of winter that you can break away from by utilizing deep, rich, highly saturated colors like burgundy or forest green.


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7) Thick Long Drape Scarf

SHOP THE SCARF—Long Drape Scarf 1: H&M (similar) | Long Drape Scarf 2: GAP (alternative)

The scarf makes an appearance on both my fall and winter essentials list. However for winter we’re talking scarves of a chunkier variety. In order to brave the elements you’ll want a long, thick scarf to protect ya neck. And you can still look stylish with a knitted or scarf with frayed edges. Stick to neutral colors so that you can wear your scarves with a variety of looks.

8) Leather Gloves

SHOP THIS LOOK—Brown Leather Gloves: H&M  | Black Leather Gloves: Elma

A pair of leather gloves are great for two reasons. They can provide both warmth and style for everyday wear. They’re versatile in that you can wear them with casual looks and more formal looks. The key is to ensure that they’re well fitting and do not have too much excess fabric. You can go black or brown here, whichever you think you’ll wear more often, though it wouldn’t hurt to have both.

9) Hat or Beanie

SHOP THE HAT—Slouch Beanie: Beechfield

Of course a winter hat is another no brainer. There are all types of hats to wear to look stylish this winter. The ones I’m recommending are the beanie or the Kevin McCallister hat (Macaulay Culkin wear it in the original Home Alone). Whether you like to fold your beanie into a normal winter hat or wear them as a slouch beanie with excess fabric in the back, you can style them to your liking. And a knitted Home Alone hat is festive, fun and is sure to keep your ears and head warm.

If it’s sub-zero temperature, feel free to go with an ushanka, one of those Russian fur caps with ear flaps. Function over form.

10) Ear Warmers

SHOP THIS LOOK—Ear Warmers: 180s | Snow Goggles: Dragon Alliance | Coat: Columbia (sold out) | Bandana: eBay

Okay, so you’ve styled your hair and god forbid if your hat were to mess that mane of male goodness up. Enter ear warmers. Sure they’re not the most stylish, but they do a great job of providing warmth and don’t look half bad.

11) Merino Wool Socks

Merino Wool Socks | Gentleman Within
SHOP THE SOCKS—Merino Wool Hiking Socks: People Socks | Merino Wool Dress Socks: Nordstrom

Why merino wool?

Well, wool breathes and wicks away moisture better than any other fabric. In fact, merino wool fibers can absorb and retain up to 30% of its own weight in moisture and still feel dry to the touch.

Not only does it dry quickly, but it’s not itchy like ordinary wool due to it’s finer fibers. You’ll also find that merino wool is more elastic and more smooth to the touch. Its moisture absorbing nature makes it static resistant. On top of all of this, merino wool has natural heating and cooling.

With these benefits in mind, a pair of merino wool socks are perfect to protect your feet from the elements in winter. Investing in quality socks (much like underwear) can be a game changer.

12) Shoe Trees

SHOP THE SHOE TREES—Shoe Tree 1: Woodlore | Shoe Tree 2: Nordstrom (alternative)

The benefits of shoe trees are three-fold:

  1. Absorbs moisture from your shoes
  2. Helps your shoes regain and retain shoe shape
  3. Keeps your shoes fresh, extending their lifespan

Go get yourself some shoe trees. I recommend one for every quality pair of shoes you have in your wardrobe.

13) Mini Flask

SHOP THE FLASK—Mini-Flask: Amazon

For when it’s cold outside, carry a mini flask. Fill her up with your favorite whiskey or bourbon. Don’t worry about looking like an alcoholic because as a stylish gent, it’ll actually enhance your status and make you appear more refined.

14) Your Favorite Winter Fragrance

Winter Fragrance | GENTLEMAN WITHIN

I recommend going out to smaller shops and boutiques in your city and get samples to try on a myriad of different fragrances. After a while, you’ll begin to gravitate towards certain scents. Get the opinion of a spouse, significant other or a friend, but in the end go with what you like the best.

I’ve worn Very Irresistible by Givenchy for about a decade now. It’s become somewhat of my signature winter fragrance. Recently I started wearing the classic Polo Blue this autumn, and just this past summer I picked up Y by Yves Saint Laurent. I adore these scents and feel great wearing them. I feel that the scents blend well with my skin, giving off a pleasant aroma that many others have complimented me on.

That’s they type of fragrance you want to find. Something that suits you. Just don’t douse yourself in cologne. Two or three sprays max is good. One on the neck, behind the neck and on the wrist. Dab a bit behind the ears if you’d like, but be sure not to rub the fragrance into your skin.

15) Lip Balm

SHOP THE LIP BALM—Lip Balm 1: Carmex | Lip Balm 2: Burt’s Bees | Lip Balm 3: Brickell | Lip Balm 4: Avon | Lip Balm 5: Nivea

No explanations needed. Our skin naturally dries up when the temperatures dip. Having several sticks of lip balm will serve you well through the course of fall and winter. I always have one in my pocket when I leave the house. I like to mix it up, but no need to go crazy with flavors or anything. Keep it simple.


There you have it, a collection of winter style for men. I’m not saying you need to have every single one of these pieces right now, but it wouldn’t hurt to build up these essentials overtime. They are pieces that can go a long way and get you through a long and harsh winter season.


Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.

Looking forward to seeing you in there.


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