Winter Accessories Every Man Should Own | Best Men’s Winter Accessories

Winter can be a tough time for your personal style, plus the weather and elements require special attention for your wardrobe and, more importantly, your accessories. That said, the right winter accessories will bring both function and personality to your wardrobe. It doesn’t all have to be about keeping warm (though that’s definitely important), it’s a great opportunity to add some extra style to whatever you’re wearing. For more basic tips, make sure to check out all of our Winter Essentials and our article on Winter Style Do’s and Don’ts

Here are our picks for the Men’s Winter Accessories That Every Man Should Own!

 

Cashmere / Wool Knit Hat

A must when it’s freezing. Go for a thicker rib knit and try cashmere for a luxurious touch that’s soft, light, and warm. Don’t be afraid to try a pop of color here too!

Hat 1

Hat 2

Budget-Friendly

 

A Patterned Scarf

The perfect time to add some color or pattern into the mix. Just a hint of it peeking out from under a coat is a sharp, stylish look. Cashmere is a great option here too, it’s very light and warm.

Picks:

Scarf 1

Scarf 2

Budget-Friendly

 

Gloves

We’re not talking about thick ski-style gloves, but something lighter but still warm. Look for knit versions in wool or cashmere or lined leather options for a sharp touch (especially if you dress up often).

Gloves 1

Gloves 2

Budget-Friendly

 

Slim Dressy Watch

Add in a thin watch that toes the line between dressy and casual so you can dress it up or down. Layered and formal outfits need a watch that’s not big and bulky. Wearing a big, sporty watch with dressier looks can just throw off the proportions. Luckily our friends at Nove watches have the perfect styles.  Their watches are high-quality, Swiss-made, and come in a variety of slim styles that work well with a range of looks. Plus, we’ve got a special deal for you guys. Use offer code AW20 for 20% off your purchase.

Picks (from the video):

Watch 1

Watch 2

 

Merino Wool Socks

Merino wool has incredible technical properties (warm, lightweight and dries quickly) and there are great options out there that are lightweight, warm, and stylish. 

Our Favorite Merino Wool Socks

Another Pick

 

Thermals

We discussed in our Winter Do’s and Don’ts, and the right pair won’t be bulky or too hot and can easily layer underneath both casual and dressy clothes. We really like our go-to pick below because they are very light, warm, and won’t break the bank.

Thermals Pic

 

Extra-moisturizing skincare products

Nobody likes the look of dull, dry skin and the cold, dry air can be brutal on your hands and face so take extra care to moisturize properly. The right products and a solid morning routine and evening grooming routine will really help keep your skin looking great during the winter.

Picks:

Moisturizer 1 – Get 30% Off With Code Ashley30

Moisturizer 2

Moisturizer 3

Moisturizer 4

 

Leather Lace-Up Boots With A Rubber Sole

Proper boots for the winter are crucial and if you’re dealing with a lot of rain and snow you want to make sure your boots are protected and have a rubber sole for traction and durability. Some of our picks below have a Dainite sole which is the gold standard in terms of protection and grip in wet, snowy conditions.

Picks:

Dress Boots 1

Dress Boots 2

Casual Boots 1

Casual Boots 2

 

Dorian’s Outfit Details

Jeans

Boots (similar)

Glasses

Peacoat

Sweater

Gloves (similar)

Scarf (similar)

Men’s Winter Style Do’s and Don’ts | Men’s Winter Style Tips

Winter can be a tough time for your personal style. Cold weather and the elements can lull you into just giving up, but don’t do it! These few simple tips can keep you looking sharp and feeling great, no matter how cold it gets! For more tips, make sure to check out our Fall/Winter Essentials Series!

Here are our Winter Style Do’s and Don’ts!

Winter Style Do’s

Do Add Some Colorful Jewel-toned Accessories

The right hats, scarves, and gloves are crucial for warmth and style. They’re also a great opportunity to add some color and pattern to brighten up your look. Colors like emerald green, a mustardy yellow, dark purples, reds, and blues are all easy to incorporate into your winter wardrobe and pack a stylish punch of color.

Picks:

Scarf 1

Scarf 2

Scarf 3

Hat 1

Hat 2

Hat 3

Gloves 1

Gloves 2

Gloves 3

 

Do Invest In Quality Outerwear

We talk a lot about where and when to invest, and outside of dress shoes & boots, outerwear is the other major area we really recommend investing in. You get what you pay for and with the right investment, a high-quality coat, peacoat, or jacket will last for years to come, keep you warm, and have you looking stylish.

Picks:

Overcoat

Overcoat 2

Parka

Puffer Parka

Parka 2

Peacoat

Peacoat 2

 

Do Get The Right thermals

There are many great brands offering very thin/lightweight thermals that’ll layer comfortably underneath your clothes and keep you warm. The key is to get a trim fit, that way they’ll lay flat and layer easily under everything from jeans to suits. Our pick below is light, warm and you can wear these as a base layer underneath your clothes or on their own as a long sleeve shirt.

Thermals Pick

 

Winter Style Don’ts

Don’t Neglect Your Skin

You may not think so, but cold-weather skincare is just as important as warm weather skincare. The cold, dry weather can be incredibly harsh on your skin and strip away it’s protection, so it’s super important to cleanse and moisturize properly and stay hydrated. There’s nothing more distracting and unattractive than dry, dull skin.

Luckily, our friends at Geologie have you covered. Geologie puts together a simple routine formulated for daily use. The products are personalized to your skin’s needs and work great for every skin type. We tested out their set that comes with 4 different products:  Everyday Face Wash, Vital Morning Face Cream w/ SPF, Repairing Night Cream & Nourishing Eye Cream. It even includes 2 bottles of face wash, one for your sink and one for your shower or to take with you to the gym. Plus, just for our readers and viewers, you can get 30% off your purchase with code Ashley30! Shop here and enter the code at checkout.

 

Don’t Forget To Layer

We talked about it for Fall, and it’s just as applicable in Winter.  Proper layering can help you regulate your temperature and look stylish no matter how cold it is, making sure you’re comfortable going from the cold outside to warm inside (subway, office, etc.).

 

Don’t Forget To Winterize your boots

Boots are essential footwear for Winter (our go-to picks for this year are right here) and the right pair can look amazing and last a long time. But, you’ve got to prepare them with the right leather treatments to keep them from getting ruined in the inclement weather.

Boot Treatment Kit

Fall Winter Coats – Parkas

When I first released my Overcoats and Peacoats video and article, all the New Englanders, Canadians and Northern Europeans complained that they couldn’t wear my favorite pieces because they just weren’t warm enough. I admit – being in Southern California definitely skews my perspective in this regard.

So let’s rectify this!

To me, there’s really only one winter jacket that I like and that looks great on everyone and keeps you nice and warm and that’s a Parka. But not all of them are created equally.

First and foremost, I keep getting asked for a “stylish” winter jacket. Honestly, when you get into crazy cold weather, I think utility should supercede style. That’s not to say parkas aren’t stylish, but no one is going to look at you in your parka and think how amazing an outfit looks.

They’re designed to go over an outfit and be taken off the second you go indoors. So if you really want to look stylish in cold weather, either throw on a fall jacket, overcoat, peacoat and layer, like your life depends on it.

 

What To look for in a good parka

Length

Depending on your climate and how cold it gets determines how long your parka should be. The longer it is, the colder your climate.

So you would wear a waist or hip-length parka if you were in an area that gets cold, but not crazy snowy.

Or if you were in the tundra, you’d wear a parka that hits your knees, or even past that.

But if you live in a climate that is somewhere in the middle, then go with a parka that hits mid-thigh.

Just don’t be that guy in San Diego wearing a knee length parka – it’s too much and looks weird.

Colors

I love Navy, Black or Olive. Do make sure the material isn’t shiny.

If I had to chose a color, I prefer Navy because it’s a very dark color, like Black, but is easily wearable. Olive is also a great color. Black can sometimes look a bit jarring in such a big jacket. But you can’t really go wrong with any of those colors.

Fit

Make sure your parka fits relatively well. That means the shoulders should fit snugly and the body should lightly hug your torso. When trying on parkas, make sure you’re wearing at least a sweater and shirt underneath so you can ensure it won’t be too tight when actually wearing it. Also make sure to zip up that bad boy in case it feels too tight in the body!

Lining

I prefer a down lining, but synthetic is also acceptable. I always find down to be a little warmer, but as always, your mileage may vary.

Detachable Fur Collar

It’s a convenience thing. So I wouldn’t disqualify a jacket for this reason, but it’s a nice thing to have because it creates a slightly different look, so I like the option whenever possible.

How To Style Your Parka

Even though they’re mostly a utility item and style takes a backseat, I couldn’t help styling a parka outfit for you. One of my favorite parkas is by Parajumpers. They do such a great job with the fit of their jackets. Anyways, I styled it over a grey crewneck sweater, wool trousers, and wingtips. And of course, I threw on a scarf and some gloves.

mens-fall-winter-essentials-parkas-ashley-weston mens-fall-winter-essentials-parkas-ashley-weston2

Parajumpers Navy Harraseeket
Topman Premium Dark Grey Ribbed Slim Fit Sweater
Brooks Brothers Leather Gloves with Black Watch Cuffs
H&M Wool Pants
Brooks Brothers Cashmere Scarf
Allen Edmonds Strand Dress Shoes
Tom Ford Snowdon Sunglasses

The Best Parkas For Men

Parajumpers Harraseeket

$1,125 –Parajumpers Navy Harraseeket

A quick note about the parkas below – You really get what you pay for. Even though there’s some budget-friendly options, I wouldn’t consider them even close to the same quality as the other parkas near the middle and top of the list. These really should be investment pieces and the overall cost of ownership will go significantly down per year if you get a high-quality jacket since it’ll last many, many years.

$2,195 – Moncler Rethel Parka (2 colors)
$1,295 – Nobis ‘The Maverick’ (2 colors)
$1,150 – Mackage Edward Hip Length Down Winter Parka with Fur (2 colors)
$1,125 – Parajumpers Harraseeket (Black or Olive)
$1,100 – Canada Goose Balmoral Parka Black Label
$1,095 – Andrew Marc Everest Fur-Trim Hooded Parka, Jet Black
$900 – Canada Goose Chateau Parka w/ Fur Trimmed Hood, Navy
$900 – Theory Jayse Padded Coal Parka
$700 – Arc’teryz Therme Parka (2 colors)
$300 – The North Face Thermoball Triclimate Black Parka
$100 – TopMan Black Short Parka 
$100 – TopMan Premium Forest Green Parka
$60 – H&M Padded Parka

Fall and Winter Casual Jackets

The best jackets for the Fall (and Winter if you live in a climate like Southern California) are bombers, trucker & flight jackets, as well as utility (aka M65 aka Safari aka Field) jackets. Now, which one you should wear depends on your body type and how you’ll be wearing it. But I’ll get into that shortly.

The goal with your jacket, just like everything else in your wardrobe, should be to create a sharp, polished look and not draw attention away from the rest of your outfit. With that being said, your jacket is a great place to insert those Fall colors ( I specifically like dark green, camel, navy or black for these jackets) I was talking about in the series intro.

If you want something a little more formal or heavier, check out my Men’s Overcoat, Topcoat and Peacoat article and video.

Trucker/Flight Jackets

todd-snyder-x-private-white-pilot-bomber-ashley-weston

$735 – Todd Snyder x Private White V.C. Shearling Melton Wool Bomber Jacket

I love a good wool or suede trucker or flight jacket for the Fall. I’m lumping these together because they look very similar. A trucker is basically a denim jacket but in a different material. I’m not going to discuss denim jackets because those are really a spring/summer item because they’re not very warm.

A trucker usually has buttons on the front and a flight jacket has a zipper front. You want to make sure your jacket stops at hip level, like a bomber would, and is fitted through your shoulders and torso. There are a ton of trucker jackets out there that have shearling or fur collars, which I really love, but I’d recommend choosing a jacket where you have the option of removing the collar, that way, you can get two different looks out of one jacket.

If you’re a broader guy, I wouldn’t recommend this jacket because the combination of the collar and shorter length of the jacket will make you look really top heavy. With your body type, whenever you have a jacket that stops at hip level, you want to make sure it’s as streamlined as possible, like a bomber.

Budget Friendly

$160 – TopMan Charcoal Wool Rich Formal Jacket
$160 – TopMan Khaki Wool Mix Flight Jacket
$150 – TopMan Black Faux Fur Collar Flight Jacket
$90 – Zara Oversized Denim Jacket 
$77 – TopMan Kahki Faux Fur Lined Flight Jacket 

Designer

$900 – Vince Suede Trucker Jacket
$950 – Vince Suede Flight Jacket
$540 – All Saints Sol Jacket 
$285 – All Saints Stram Denim Jacket 

Bomber Jackets

A.P.C. Louis W Suede Bomber Jacket

$1,455 – A.P.C. Louis W Suede Bomber Jacket

Speaking of bomber jackets, I consider them the utility infielder of the jacket world. I use them all the time with clients because they look great on every man, regardless of his body type. They break up your body at the waist nicely, keeping everything proportional.

If you’re a guy with a larger midsection, the one thing to watch out for with bomber jackets is zipping it up. If you do that, you just created a large swath of fabric that’ll actually accentuate your mid-section. So if you’ve got a bit of a belly or are just a bigger guy, do not zip up your bomber jacket, ever. And I’m not joking about that, either.

Budget Friendly

$138 – J. Crew Wallace & Barnes Boiled Wool Bomber Jacket
$100 – TopMan Navy Bomber Jacket Containing Wool
$100 – TopMan Stone Bomber Jacket Containing Wool 
$80 – Zara Faux Suede Bomber Jacket (Stone and Navy Blue)
$80 – Zara Faux Suede Bomber Jacket with Stripe

Designer

$1,495 – Rag & Bone Gallagher Leather Bomber Jacket
$795 – Hugo Boss Embossed Suede Navy Bomber Jacket 
$700 – John Varvatos Burnished Leather Bomber Jacket
$650 – PS by Paul Smith Bouclé-Panelled Wool-Blend Twill Bomber Jacket

Utility Jackets

Parajumpers Genesee Urban Anthracite

$800 – Parajumpers Genesee Urban Anthracite

The last type of jacket I love for Fall and Winter is a utility jacket, aka Safari, Field, or an M65 jacket.

This jacket differs from my other favorites because if it fits well, it’ll hit somewhere between mid to lower crotch – so it’s a great option if you want a longer jacket. But please, nothing longer or shorter than that, otherwise it’ll throw off the proportions of your body.
I really like this style for heavier men, almost more than a bomber or trucker style because the slightly longer jacket length and pockets on the front break up your broader torso and will make you look smaller.

And if you’re a thinner guy – just beware of this style of jacket that has a hood in the collar because it will look too bulky/heavy around your thinner frame, especially the neck area, and will actually make you look skinnier. Instead, you need your jacket to have a standing collar or at least a collar that’s free from any puffiness.

Regardless of your body type, this type of jacket needs to be very fitted throughout so it doesn’t look like you’re swimming in a bunch of pockets and fabric. This is important because it can make a thin guy look skinnier and a broader gentlemen look even heavier than he is.

Budget Friendly

$200 – J. Crew Field Mechanic Olive Jacket
$200 – J. Crew Field Mechanic Navy Jacket
$180 – TopMan Grey Bonded Wool Blend Parka
$130 – Calvin Klein Four-Pocket Utility Jacket (2 colors)

Designer

$7,400 – Tom Ford Suede Military Jacket
$1,600 – Todd Snyder Suede Quad Jacket in Tobacco
$1,500 – Moncler Ampere
$750 – Club Monaco Golden Bear Field Coat 

Materials

I like suede or leather for Fall/Winter because it’s visually heavier, but just be careful about wearing suede in wet or snowy weather. But if you don’t want leather or suede, you can use a cotton or wool bomber or trucker, as well.

For utility jackets, anything but leather goes. They look a little too 70’s pornstar-ish to me.

Best Ways To Wear Your Fall Jackets

fallwinteressentials-bomber-jacket-ashleyweston2

fallwinteressentials-bomber-jacket-ashleyweston

J. Crew Wallace & Barnes Boiled Wool Bomber Jacket
Brook’s Brothers Golden Fleece 3-D Knit Fine-Gauge Merino Wool Brown Crewneck Sweater
Allen Edmonds Black Poplar Dress Belt
Burberry Slim Fit Wool Trousers
Allen Edmonds First Avenue Dress Boots
Rolex Submariner Date Watch
Tom Ford Snowdon Sunglasses

fallwinteressentials-bomber-jacket-ashleyweston3 fallwinteressentials-bomber-jacket-ashleyweston4Topman Khaki (Green) Wool Flight Jacket
H&M Premium Cotton Shirt
Allen Edmonds Black Poplar Dress Belt
Burberry Slim Fit Wool Trousers
Allen Edmonds First Avenue Dress Boots
Rolex Submariner Date Watch
Tom Ford Snowdon Sunglasses

fallwinteressentialsutility-jacketashleywestonoutfit22

fallwinteressentialsutility-jacketashleywestonoutfit2

Parajumpers Genesee Urban Jacket
H&M Premium Cotton Shirt
Diesel Buster 0607A Jeans
Allen Edmonds Black Poplar Dress Belt
Allen Edmonds Long Branch Wingtip Boots
Tom Ford Black Snowdon Sunglasses

Fall and Winter Boots For Men

There’s 3 types of Fall and Winter Boots for men that I love for this time of year – Dress, casual and chukka boots.

The reason I love boots for Fall/Winter is that they go so well with jeans, wool trousers and fall/winter suits. They also do a great job of keeping your feet warm and protected from the elements – while looking classy and more refined than a pair of hiking boots or something that’s just a straight utility item.

Now, if you live in an area with a good amount of snow or rain, then you should probably have specialty boots for the crazy days, too, but those are outside the scope of this article. 

The difference between dress and casual boots

Dress boots are more formal and can be worn with a suit or wool trousers. They have a sleeker profile, usually leather or dainite soles, and are made out of shinier calf skin, as opposed to cow hide. Dress boots are like dress shoes with a shaft, basically.

Casual boots usually have more room in the toe box, the leather is usually a thicker cowhide that is more matte, and the soles usually have lugs on them. They look a little less dressy and sophisticated, which is why they look so great with jeans, but you can also still wear them with wool trousers.

My Requirements for a good Fall/Winter Boot

These items apply to all the types of boots – dress, casual and chukka boots:

1. A slim profile and not chunky

Timberlands (right) are the exact opposite of what I’m looking for in a good boot. You want a nice, rounded toe box with a slim profile as well as sole like the image below.

dressvsworkbootashleywestoncropped

2. Plain, Cap Toe or Broguing

I like all 3 of them, but just like with my dress shoes, I’ll always prefer a plain or cap-toe, but broguing is also acceptable. Broguing is not really my preference because I think a lot of guys overdo it with the broguing, burnished toes, etc. Too much can easily look gaudy if you’ve got too much going on in your outfit.

plaincaptoebroguingashleyweston

3. Lugged, Dainite or Rubber soles

These will give great grip in any type of weather. A normal dress boot has smooth leather on the bottom and you will slip and slide like crazy in wet weather. If you’re not in a climate with rain/snow, then you can go with straight leather bottoms typically found on most dress boots, but I see no reason to do that when any rubber bottom aside from lugged will look very similar with the extra benefit of additional traction.

mensleatherbootsolesashleyweston

4. Be brown or black leather

Go with nice dark chocolate or walnut brown first, then get black if you don’t have them already. Brown is a great fall/winter color and is easier to wear with casual AND more formal outfits. But be careful about getting a really specific brown color, like oxblood. As I’ve said in my other shoe videos, it’s a great color but doesn’t compliment a lot of outfits, so get that color once you’ve got these basics down.

And please, whatever you do, don’t get those terrible boots that are already worn in. It’s much better for you to wear them in yourself and really personalize their look to your actual lifestyle.

5. NOT be Suede

For Fall and Winter boots, suede is the last material you should consider, unless you live in a dry climate like Southern California where it rains maybe 3 or 4 times a year. Otherwise, they’ll get screwed up very quickly with any amount of rain or snow. I don’t care how much scotch guard you use, nothing can stand up to that much abuse. So save the suede shoes for spring, please.

Can I wear boots with a suit?

Yes, but only when these 2 conditions are met:

  1. You’re wearing a heavier wool or tweed suit.
    For a visually heavy item like boots, you should understand fabric weights and pairing them with similar items. Even straight up dress boots can look odd with lighter weight wool suits. Make sure the wool is atlas 12oz thick. The easiest way to tell what a heavy wool suit feels like in person, is it should be as thick as a wool sweater (not as soft, though!)
  2. Your pants are hemmed to have no break.
    The hem of your pants will look sloppy and bunched at the ankle, otherwise. You can technically cuff the hem of your suit pants to do this, but if they’re super long, it’ll never look quite right. So I usually just get the pants hemmed to no break for this. But that means you can’t wear this suit with anything but boots now…unless you have your tailor let out the hem when the seasons change.

How To Tie Your Boots

Check out my shoe and boot tying video for how to tie your shoelaces properly.

Best Ways To Wear Boots For Men

fallwinteressentialsbootsashleywestonoutfit1

Topman Black Cotton Bomber Jacket 
TopMan Ribbed Turtle Neck Slim Fit
Rolex Oyster Perpetual Submariner Date
Tom Ford Black Snowdon Sunglasses
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt

fallwinteressentialsbootsashleywestonoutfit2

Parajumpers Anthracite Urban Genesee Jacket
Brooks Brothers Milano Fit Button-Down Collar Dress Shirt
Rolex Oyster Perpetual Submariner Date
Tom Ford Black Snowdon Sunglasses
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Dress Belt

fallwinteressentialsbootsashleywestonoutfit3

Topman Faux Suede Flight Jacket (It’s technically a Peuterey jacket, but it’s only available in Europe)
Brooks Brothers Milano Fit Spread Collar Dress Shirt
IWC Portuguese Automatic Watch
Tom Ford Black Snowdon Sunglasses
H&M Black Melange Wool Suit Pants
Allen Edmonds Decatur Ave Dress Belt

The Best Fall Winter Boots For Men

Casual Boots

Budget Friendly

Aldo Acerrassi

$200 – Aldo Acerrassi

$175 – Aldo Etausen Boot (2 colors)
$175 – Johnston & Murphy Conard Wingtip Boot (3 colors)
$220 – Jack Erwin Carter Wingtip Boot (2 colors)

Designer

$350 – Allen Edmonds Long Branch Wingtip Boots


$318 – FRYE Tyler Lace Up (2 colors)
$395 – Wolverine 1000 Mile Boot 
$725 – Crockett & Jones Coniston Tan Boot
$775 – Crockett & Jones Islay Wingtip Boot

Dress Boots

Budget Friendly

Calvin Klein Darsey Brown Boot

$140 – Calvin Klein Darsey Dark Brown Leather Boots

$60 – Stafford Deacon Wingtip Leather Boots (2 Colors)
$135 – Stacy Adams Madison Boot (2 colors)
$140 – Calvin Klein Darsey Black Leather Boot

Designer

Allen Edmonds First Avenue Black Boot

$995 – Saint Laurent Polished Leather 

$645 – O’Keefe Algy Split-Toe Weatherproof Pebble-Grain Leather Boots
$748 – Brooks Brothers Peal & Co. Leather Wingtip Boots
$1,098 – Brooks Brothers Peal & Co. Cordovan Boots

Chukka Boots

Budget Friendly

Johnston & Murphy Fulton Chukka Black

$140 – Johnston & Murphy Fulton Black Chukka

$130 – Clark’s Desert Boot in Brown Suede
$75 – Aldo Granges Chukka Boot
$175 –Johnston & Murphy Conard Cap Toe Chukka (2 colors)
$198 – Johnston & Murphy Fulton Brown Chukka
$225 – Vince Camuto Branx Two-Eye Chukka (2 colors)

Designer

Allen Edmonds Dundee 2.0 Chocolate

 

$250 – Allen Edmonds Dundee 2.0 Suede Boots (2 colors)
$378 – FRYE Weston Chukka (3 colors)
$1,500 – John Lobb Elmer Chukka

 

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