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

Henley Shirts

Henley shirts are one of the few items that, to me, don’t really have a specific season they’re best worn in because there’s so many different versions for men. Other shirts, like T-Shirts, Polo Shirts and Dress Shirts don’t really have this problem since they’re pretty standard across the board no matter the season.

I love henleys, because they look sexy and masculine, especially when the top 1 or 2 buttons are undone to draw the eyes to your chest and shoulders to show off your physique in a flattering way. Hence, the image below.

BUT, and this is a big mistake I see a lot of men making – they’re not for every everyone. More on that shortly.

Let’s get into what to look for in your henleys based on the time of year.

Intro - Short Sleeve Sexy henley

Fabric

Generally, henleys will be made out of cotton, so there’s really not much choice outside of that, but you still need to consider fabric weights depending on the time of year. The main thing to know is that lighter weights should be worn in warmer months or in warmer climates and thicker, heavier fabrics in cooler months or climates. You can get them in everything from a lightweight summer weave, where it feels like a t-shirt, to thicker, quilted versions which will keep you warm during the cooler months.

You don’t have to worry too much when buying them because, based on the time of year, the brands will carry the appropriate weights. But I still want you to be aware of it just in case.

Henley Fabric Ashley Weston 2

Fit

Like all your clothing, including henleys, they should have a trim fit throughout the body and arms – no matter your body type. You never want it too loose anywhere because that’s when you’ll look sloppy and not put together. You shouldn’t be able to pinch more than 1-2 inches of fabric on one side of your stomach and no more than an inch around the bicep.

The image below highlights the proper fit around the torso and sleeves.

Fit - Perfect fitting henley shirt

I mentioned earlier that henleys aren’t for everyone, so let’s get into that right now since we’re talking about fit.

For Thin Gentleman

If you’re a thin guy, no matter your height, if you want to wear a henley, you absolutely need to nail the fit, especially if you’re going to wear a long sleeve version. If the fit is too loose, it’ll make you look thinner and more frail than you are – not good!

I only like long sleeve henleys on thinner men if they’re layered underneath a jacket, like the below right image. When worn on their own, it really spotlights and elongates your thinner torso, like image on the left. So if you’re a thinner guy and want to wear a henley on its own, then wear a short sleeve version since it’ll look similar to your t-shirts.

Henley Fit Ashley Weston

Bigger Gentleman

If you’re a rotund gentleman (aka you’re not in the greatest shape and have a belly), you cannot wear a henley shirt, period. Allow me to show you why and explain. See exhibit A:

Fit - Big Guy - Bad Example of henley

Because of the button placket on the front, coupled with the lack of a collar, a henley will shine a massive spotlight on your bigger neck and torso. This is when a polo shirt is perfect and should be used instead, because a polo shirt’s collar will visually keep your torso balanced and in proportion, so your top half doesn’t look so big compared to your bottom half. The image below of James Corden shows a guy with the exact same body type as the image above, but in a polo shirt. Talk about a night and day difference…

Fit - Big Guy - Good Example - Polo Shirt1

Best Ways To Wear A Henley Shirt

Think of your short sleeve henley as a t-shirt, they’re interchangeable in the same outfits, so that means they can be worn on their own or underneath a jacket.

How To Wear Henley - Short Sleeve

J. Crew Slim Broken-In Short Sleeve Henley
J. Brand Tyler Taper Fit in Rasalas
Allen Edmonds Hampton Ave Tan Leather Belt 
I would pair this look with white sneakers – Nike Tennis Classic Sneakers

For a long sleeve, you would normally wear these during the cooler months as a layering piece, so I styled Dorian in a long sleeve henley shirt underneath a bomber jacket, dark wash jeans, and sneakers.

Mens-Henley-Shirt-Long-Short-Ashley-Weston-2

Mens-Henley-Shirt-Long-Short-Ashley-Weston-3

Burberry Lightweight Lambskin Bomber Jacket 
J. Crew Wallace & Barnes Wool Henley Sweater
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Black Dress Belt  
Johnston & Murphy Conard Cap Toe Black Chukka

IWC Portugieser Automatic Watch
Ray Ban RB4258 Sunglasses 

During the warmer months you can wear them with the sleeves pushed up. As I mentioned in one of my other videos, women LOVE to see sleeves rolled/pushed up around your forearms.

How To Wear Henleys - Henley Sleeves Pushed Up On Forearms

My Favorite Henley Shirts

Here are some great short sleeve and long sleeve (lightweight and heavyweight) henley options that I love.

Short Sleeve Henleys

Short Sleeve Henley 1 Ashley Weston

$125 – Rag & Bone Classic Short-Sleeve Henley
$35 – J. Crew Slim Broken-In Short Sleeve Henley (White, Navy, Heather Grey, Black)

Long Sleeve Henleys

Rag & Bone Long Sleeve Henley Ashley Weston

$250 – Rag & Bone Giles Merino Wool-Blend Heavyweight Long Sleeve Henley Shirt
$40 – J. Crew Slim Broken-in Lightweight Long Sleeve Henley
$15 – H&M Jersey Lightweight Long Sleeve Henley 

Wool Blazers & Sport Coats

I’m sure you’ve already seen my article/video about a Navy Wool Blazer in my Wardrobe Essentials Series, riiiiiggghhht? If not, then please read and watch it first before we talk about Fall and Winter wool blazers/sport coats, because I’m going to assume we’re on the same page in regard to the differences between a blazer, sport coat and suit jacket as well as how your blazer should fit your body type as well as the finer details of what to look for in a quality blazer. Otherwise, you will probably be lost or think this article is a little anemic. There will be a few critical differences between your year-round blazers and your specific Fall and Winter wool blazers. So let’s get into them.

1. Fabric Weight

The most important difference during this time of year is the fabric weight of your blazer.

You want a much heavier wool fabric, like Harris Tweed, for three reasons:

  1. It will keep you much warmer during this time of year.
  2. The heavier weight pairs better with similar weighted fabrics during this time of year – Like your wool ties and pocket squares, wool trousers, sweaters, cardigans, etc.
  3. If it has a tighter weave, like Harris Tweed, it’ll be more durable, robust and repel water and snow better.

To get technical for a moment, a typical weight you should look for is around 12 ounces, but you can go all the way up to 16 to 20 ounces. For year-round wool blazers, I prefer a fabric weight of between 8 to 10 ounces, depending on your climate. In comparison, for hotter climates/seasons, I usually go with somewhere around 6 ounces for the fabric weight.

You’ll instantly notice the difference of fabric weights when you feel the blazer in-person. It’s a little harder to see it in in pictures, so I would suggest going to a store that carries suits to see it for yourself.

Long story short, you want a thicker wool for this time of year.

2. Color

The second difference is the colors for the time of year. Unlike the year-round wool blazers, this is the time of year where you can wear richer, more jewel-toned colors, all based on your skin tone, of course.

The best way I can describe colors is to think of the leaves changing to their fall colors and those are the colors you want for the season. So that typically means these colors:

  • Browns
  • Burgandys
  • Greens
  • Blues
  • Oranges

I went over all these colors and how to wear them based on your skin tone in my introduction article & video to this series.

3. Patterns

The last and final thing to consider for your Fall & Winter wool blazers are the patterns. Since you’ll be wearing heavier items, bold and heavier patterns work great this time of year.

My favorites are:

All of these patterns are included in my selects from various brands below.

Best Ways To Wear A Wool Blazer During Fall & Winter

MensFallWinterEssentialsWoolBlazerAshleyWeston

MensFallWinterEssentialsWoolBlazerAshleyWeston-2 MensFallWinterEssentialsWoolBlazerAshleyWeston-3

H&M Dark Khaki (Green) Blazer
J.Crew Cotton-Cashmere Crewneck Sweater in Jacquard
The Tie Bar Kingsley Attune
H&M Wool Suit Pants
Aldo Acerrassi boot
Rolex Submariner Date
Tom Ford Snowdon Sunglasses

MensFallWinterEssentialsWoolBlazerAshleyWeston-10

 

MensFallWinterEssentialsWoolBlazerAshleyWeston-11 MensFallWinterEssentialsWoolBlazerAshleyWeston-4

Topman Light Brown Wool Rich Formal Coat
The Tie Bar Chambray Shirt 
The Tie Bar Wentworth Plaid 
The Tie Bar Kingsley Attune Pocket Square 
The Tie Bar Metallic Navy Tie Bar
Diesel Buster 0607A Jeans
Allen Edmonds Poplar Dress Belt
Johnston & Murphy Cormac Double Buckle Monk Strap
John Varvatos Prince Sunglasses

MensFallWinterEssentialsWoolBlazerAshleyWeston-12

MensFallWinterEssentialsWoolBlazerAshleyWeston-5

MensFallWinterEssentialsWoolBlazerAshleyWeston-6

H&M Wool-Blend Blazer Slim Fit
Brooks Brothers Milano Spread Collar Dress Shirt
The Tie Bar Score Check Tie 
The Tie Bar Olive Green Tie Bar
The Tie Bar Southeast Plaid Pocket Square
Diesel Buster 0607A Jeans
Allen Edmonds Poplar Dress Belt
Allen Edmonds Strand Cap-Toe Oxfords with Dainite Rubber Sole
IWC Portugieser Automatic Dress Watch
Tom Ford Snowdon Sunglasses 

All of these blazers are from companies that I love. Zegna, Canali, and Brooks Brothers’ blazers have superior construction and the fit, color, and pattern are exactly what I look for in a standout blazer for my clients. For more budget-friendly options, I really like J.Crew’s english tweed sportcoats. The weight of these blazers are perfect and the solid textured colors (brown, grey, and navy) will never go out of style. For a nice camel or dark green blazer, Topman and H&M, respectively, make these nice blazers. The fabric isn’t as thick as I’d prefer, but the price point is hard to beat so I’m willing to overlook that.

$2,895 – Ermenegildo Zegna Windowpane Two-Button Sport Coat
$1,595 – Canali Tic Two-Button Sport Coat
$538 – Brooks Brothers Milano Fit Multi-Windowpane Sport Coat
$418 – Brooks Brothers Fitzgerald Fit Blue Harris Tweed Tic with Windowpane Sport Coat
$350 – J. Crew Ludlow Legacy Blazer in American Wool
$220 –Topman Light Brown Wool Rich Formal Coat
$200 – TopMan Selected Homme Navy Blazer
$70 – H&M Dark Khaki Blazer

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