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

Men’s Wardrobe Essentials: Lightweight Jackets

You know that confusing time when it’s still jacket weather but the temperatures are fluctuating from warm to cold and you’re chilly one minute and sweating the next? Yeah, it’s not easy to dress for that, is it? You’ve probably seen the word “transitional” used in and around this time relative to your wardrobe, but really it’s just a fancy word for “versatile”. With versatility and changing seasons in mind, let’s discuss a major key to a solid “transitional” wardrobe, the right lightweight jacket.

Whether you’re in bomb cyclone territory or more temperate parts of the country, the ideal lightweight jacket (or two!) is an important element because you can layer up or down depending on temperatures, all while maintaining style and a comfortable temperature. There are a million different versions in all manner of materials, but until you’ve completely nailed all the essentials, I recommend sticking to the classics for versatility, style and ease of wearing. No matter which one you choose or what the weather app on your phone is telling you, you can layer up confidently (t-shirt, collared shirt, sweater, whatever) for anything from work to a night out.

The Bomber Jacket

Also sometimes known as the MA-1 and tracing its lineage back to the uniform jackets designed for military pilots in World War II, the classic style and functionality of a bomber remains just as strong today as it was back then. Featuring a zip front, elastic waist and cuffs, and a low-profile collar, you can find stylish versions of the bomber in every conceivable material, from nylon and wool to cotton and suede. I absolutely love the versatility of a bomber jacket, and as I’ve said before, every man, regardless of age or body type, should have one in his closet.

outfit details here

Who Should Wear It

All body types and ages look great in bomber jackets – as long as it fits well – close to the body with arms and shoulders fitted like the above picture.

How To Wear It

A casual staple that’s infinitely versatile, the Bomber looks right at home with everything from a t-shirt and denim to chinos and a chambray or oxford shirt. Make sure the shoulder seams sit properly, almost exactly like how your suit jacket or blazer should fit and know that a bomber jacket that fits properly should stop right around your waist. Most bomber jackets are slightly shorter in the back, too, so don’t think something is wrong if you notice that. A longer bomber jacket tends to look odd and sloppy, so avoid it if you can.

For outfit ideas, see this article, as well as points 3 & 4 in this article/video.

The Trucker Jacket

Just like it’s close cousin the Bomber, the trucker jacket was born out of utility and remains a classic style piece to this day. Typically of shorter length and hitting around the hip/waist, the workwear-inspired trucker jacket often features a button or zip front, fabric-covered collar, and handy flap pockets on the front. I like all types of materials for trucker jackets but you’ll most commonly find them in sturdy waxed cotton or canvas (to protect against the elements), denim, and nylon.

outfit details here

How To Wear It

Another one my go-to casual recommendations, I love a trucker jacket with denim and desert/work boots. It looks stylishly masculine but still polished enough to be worn over a collared shirt without looking like you’re commuting to work on a horse.

For my favorite trucker jackets and the best ways to wear them, check out this article.

The Field Jacket

Going by many names (M65, Utility Jacket, Safari Jacket), this essential is just another example of how functional military-inspired designs still look sharp and stylish today. It’s slightly longer length should hit just past the hip and it commonly features multiple sets of pockets for extra utility when you’re on the go. The Field Jacket is a great protector against the weather yet light enough for the Spring’s rapidly changing temps, so look for it in cotton and nylon versions. Forest or Olive green colors are more traditional but I’m a big fan of navy (my favorite), darker browns or grays, as well.

Who Should Wear It

Stockier or larger men. The multiple pockets help break up your large top half and give a slimming appearance.

Who Shouldn’t Wear It

If you’re a slimmer guy and not 100% confident in how to wear this, avoid it because it’ll can make you look slimmer and like you’re swimming in pockets and fabric. I see this mistake more often than not. So when in doubt, skip it.

How To Wear It

Layer it over a cashmere sweater and an oxford or even your favorite dress clothes to add a bit of contrasting ruggedness to a polished look. Of course, it’s always perfect for your weekend morning coffee runs with t-shirts, jeans or tailored sweats too. I’d avoid wearing it with chino pants because the fabric weights are too similar and you’ll look like a 70’s action star pretty quickly. Ideally, you want something heavier on the bottom – jeans or wool trousers.

For my favorite field jackets and best ways to wear them, check out this article.

The Harrington Jacket

I’ve talked about my love of the Harrington jacket before, and for good reason, this jacket strikes that perfect sweet spot between casual and sporty and goes with pretty much anything. Look, if it’s good enough for style icons like McQueen, Elvis, and James Dean, it definitely deserves a place in your closet. The Harington blends a slight preppy edge with the functionality of a windbreaker and most often features a light cotton or nylon shell, zip-up front, and barrel button collar. Whether on the links, out and about, or heading to drinks, the Harrington has you covered. 

Who Should Wear It

All body types and ages look absolutely fantastic in a Harrington.

How To Wear It

The Harrington’s preppier look and vibe pairs perfectly with staples like chinos, t-shirts and button-ups, but it just as easily transitions to a casual evening out when layered with a light sweater, dark denim and sneakers or loafers. For more in-depth details, see this article/video.

The Denim Jacket

While it’s at home on the range or in a 50’s movie star’s vintage Porsche, the denim jacket can be just as stylish and useful to you on your own city streets. A classic for a reason, the denim jacket has seen a recent resurgence to staple status now that denim is pretty much everyday wear. While this short, button-up jacket doesn’t offer a ton of warmth, it’s vintage throwback style, when paired with a crisp white t-shirt or layered over a light cotton sweater, more than makes up for it.

outfit details here

Who Should Wear It

Everyone! It looks right at home on men of all ages and body types. The only caveat is if you’re an older man (50’s and above) you may want to avoid lighter colors, as it tends to look a little “trying to dress too young”, so stick to darker indigos or black if that’s you.

How To Wear It

Properly pulling off the Canadian Tuxedo is a very dicey (impossible?) move, so keep it simple and pair with chinos and black or dark denim, or opt for colors like grey, black, indigo, or light-washed denim. On the fit side, it needs to be tight in the arms and body and stop at the upper part of your waist, so keep it trim and short to avoid looking boxy or like a 90’s R&B music video backup dancer.

For more details, check out my more in-depth article/video here.

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