Stay warm and stylish this winter with my top 15 essential items for men. From practical outerwear to trendy accessories, I’ve got you covered for the colder months. I also included bonus men’s winter style outfits at the end of this post to inspire your fits this season.
All style inspo. is taken from my Gentleman Within Instagram account as well as my personal Insta.
Men’s Winter Style Essentials
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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 Leather York Ankle Boots (similar) | 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 moctoe. Hard to go wrong with any of those. Take your pick.
Me personally, I’m loving a pair of dark suede boots. It’s ultra stylish, and darker shades of olive, blue and brown is as versatile as ever. Plus it’ll stand out from the sea of standard leather boots you’ll see out in the wild.
2) Turtleneck Sweater
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.
» READ MORE: Types of Fashionable Sweaters for Men (The Ultimate Guide)
3) Shawl Collar Cardigan Sweater
SHOP THIS LOOK—Flannel Shirt: Bonobos | Cardigan: L.L. Bean
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: Amazon Fashion (similar)| Trousers: Banana Republic | Boots: Thursday | Gloves: Alepo | Scarf: Rothco
SHOP THIS LOOK—Peacoat 1: Schott NYC | Peacoat 2: Amazon Fashion | Peacoat 3: Kenneth Cole
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.
Related: You might like this article on Best Men’s Winter Coats.
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 that you use to remove pet hair can come in handy for anything wool. Since a roller is too big when you’re on-the-go, keep a small lint brush in your coat pocket at all times.
5) Wool Trousers
SHOP THIS LOOK—Wool Trousers: Nordstrom | Shoes: Allen Edmonds | Watch: Stuhrling | Necktie: Amazon Fashion
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.
Subscribe to the GW YouTube channel.
7) Thick Long Drape Scarf
The scarf makes an appearance on both my winter and fall 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
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 wears 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 | Bandana: Amazon Fashion
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
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.
» READ MORE: Fall & Winter Fabrics Guide (Everything You Need to Know)
12) Shoe Trees
SHOP THE SHOE TREES—Shoe Tree 1: Woodlore | Shoe Tree 2: Nordstrom (alternative)
The benefits of shoe trees are three-fold:
- Absorbs moisture from your shoes
- Helps your shoes regain and retain shoe shape
- 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 | Copper Leather Flask: Whiskey Leatherworks (premium)
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. I actually just picked up Whiskey Leatherwork’s, Clark Fork Copper Flask from Huckberry this winter.
14) Your Favorite Winter Fragrance
I recommend going out to smaller shops and boutiques in your city and get samples to try on a myriad of different scents. 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. These are just a few fragrances among the dozen or so I’ve acquired through the years.
The type of fragrance you want to find is 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.
» READ MORE: A Primer on Choosing the Right Fragrance & How to Apply It
15) Lip Balm
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.
Bonus: Winter Style Inspiration
In the End
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.
Onto you. What are some of your favorite winter style essentials?
Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.
Looking forward to seeing you in there.
As it gets colder I’m never sure what to where. Honestly, feel like I only have a sweet wardrobe for the summer haha! Thanks for these great ideas. About to order a scarf and some snazzy merino wool socks right now!
Awesome! I’m glad that this was helpful. The colder weather definitely gives more opportunity to elevate your style. Cheers, –K.