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 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