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.
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.
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.
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.
Now that we’re headed into Fall it’s about time you start thinking about your sweater rotation. While cashmere is expensive, it’s no longer just a true luxury item, and you can now find cashmere sweaters at multiple different price points. We get asked about cashmere sweaters a ton so we thought it was time we gave you our opinion on whether or not cashmere was worth it.
Pros:
-Very light, soft, and warm. Cashmere is the ideal material for sweaters.
-They are extremely comfortable and layer easily.
-Have a nice finish that can be dressy or casual.
Cons:
-Expensive to very expensive.
-Delicate and require extra care. Not as durable as merino wool or cotton versions.
-Cashmere sweaters now come at a huge range of price points so it can be tough to know the quality.
There’s only a few weeks of Winter left, so pretty soon we’re all going to have to start thinking about transitioning to our Spring wardrobe. So in addition to your year-round Men’s Essential staples that are already in your closet, Jordan O’Brien from The Gentlemans Cove and I each came up with a list of 10 Spring Essentials that every man should own.
My Top 10 Men’s Spring Essentials
1. Lightweight, Spring Suit
Whether you go with a linen, cotton, seersucker, or lightweight wool suit, these options will make a statement and keep you cool throughout the Spring and Summer months.
These lightweight blazers are perfect for casual Fridays at work or heading to lunch or dinner with friends. They’re a great way to insert a stylish statement while keeping cool. Linen will wrinkle a bit, but that’s part of its character so embrace it.
I love gingham shirts for the Spring because they can be worn dressed up with a suit or blazer or dressed down on their own or underneath a sweater. I included some great lavender, navy, and light grey gingham options below.
There’s no other brand that I love more than The Tie Bar. The quality, construction, and color/pattern choice can’t be beat by any other brand. Like I’ve always said, they’re not paying me to say this.
Polo shirts instantly make an outfit look more put together and Spring is the perfect time to start wearing them. I like John Varvatos, but be careful if you’re not in shape or have erect nipples because their silkier shirts will highlight these areas. The fit on Theory and Fred Perry polos is excellent and H&M is my go-to when I’m more price-conscious. You’ll need to replace those roughly every 8 weeks though due to fading.
Not only do short sleeve button-up shirts look stylish, but every man (regardless of age or body type) can wear these. There’s currently so many great options from J.Crew and come March/April, Topman will have an equally great selection.
I’ve maintained in some of my other videos and articles that you should save your suede for Spring. Well, it’s time to break out those items. I love the options below – you can choose from navy, light grey, and brown suede jackets. The A.P.C. jacket is a BIFL piece and will never go out of style.
Finally we’re entering ankle season, which means penny loafers can finally be worn. I love Ferragamo’s loafers (I got a pair for my fiance Dorian 2 or 3 years ago) and they’re totally worth the price because they definitely hold up and still look great after years and years of wear.
Suede monkstraps, whether you get a dark brown, grey, or navy pair, can just take an outfit to another level. It’s such a stylish touch to any outfit and can be worn with a suit, chinos, or jeans. Make sure to Scotch Guard them before you wear them for the first time – always gotta protect your suede items!
Chinos should only be worn in Spring, Summer, and early Fall and that’s it. They’re a great alternative for those days when you don’t feel like wearing jeans and when you want to just feel cool and comfortable.
These as well as other great alternatives were included in my Summer Essentials E-Book. A lot of Jordan’s picks I actually included in that e-book so be sure to check it out if you haven’t already 🙂
Linen, as well as the other lightweight fabrics I also included in my list, is very breathable and will keep you cool during the warmer months. Here are some of my favorite items currently available.
Whether you need some extra sun protection or want to look stylish while staying cool, straw hats are super breathable and lightweight. Every year I get J.Crew’s panama hat, but it only lasts the season before it starts to fall apart. I’m currently eyeing Loro Piana, Brooks Brothers and Stetson’s hats because I know I can count on the quality and construction.
I like long sleeve henleys when they’re worn as a layering piece, so underneath a casual button down shirt paired with some dark wash jeans and boots or sneakers. If you’re a slim or wider gentleman, I highly advise against wearing henleys on their own because they emphasize your body size even more (and not in a good way).
If you’re new to wearing denim jackets, I suggest going with a black or dark grey version because it’ll be a lot easier to wear, especially if you wear jeans a lot because you don’t want to look like you’re wearing a Canadian tuxedo.
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.
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.
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.
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.
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.
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.
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.
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.
Andrew Snavely from PrimerMagazine.com joined me to compare our lists of the Top 10 Men’s Summer Essentials – with a disgusting twist.
If you don’t know the Bean Boozled Challenge, it’s a game where you have a 50/50 chance of getting a delicious jelly bean or one that’s flavored something like vomit, skunk, rotten eggs and a whole host of really vile flavors.
If our items didn’t match up, we had to spin the wheel of doom and see what flavors we got. I wish I could say this is the first time I’ve played this game, but unfortunately, I’ve had the pleasure of playing it before.
If I had a dollar for every poor-fitting polo I’ve seen, I’d have my own moneybin! So let’s make sure you look amazing while wearing your polo shirt. As I always say, these rules apply to any man, no matter your age or body type.
Collar & Neck Opening
The size of the collar isn’t something you need to be concerned with as they’re pretty standard across all brands. Just make sure they’re not too small.
However, do pay close attention to the buttons – specifically, you want to make sure the buttons end no further than the top of your armpits. Anything past that, like the image below, is too long and will look like a super deep v-neck when un-buttoned – not good.
Wearing a polo shirt with the top 1-2 buttons left unbuttoned will help frame your face better and make it look great. So when trying on a polo shirt for the first time, make sure to unfasten the top 2 buttons, regardless of whether it’s a 2, 3 or 4 button polo, to see how the neck opening sits on your body. You don’t want the collar/opening to lay completely flat on your chest like this:
You want it to stand up a little bit and have some structure like the image below. But the inverse of that, is you don’t want it so stiff that even when unbuttoned, it doesn’t spread out a little bit.
All of images of the different ways to wear a polo shirt in my Essential Polo Shirt Video & article have the perfect neck opening and button placement.
Sleeves
The sleeves should hit around mid-bicep and lightly hug your arms. Some polos have a ribbed band at the end of the sleeve where it’ll hug a little tighter, which is fine, as well. Regardless of this, the sleeves shouldn’t be too tight where it looks like your biceps are being strangled. You also don’t want there to be bunch of slack or room around the bicep, either. That just looks cheap and tacky and makes your arms look really small in the worst way possible. If the polo fits well everywhere else, have your tailor slim them down to fit your arms better.
Body/Torso
Like I say in all my shirting articles, the perfect fitting polo will be when you can pinch (not pull) between 1 to 2 inches of fabric on either side of your stomach. This goes for EVERY SINGLE BODY TYPE. A lot of my larger clients fight me on this… until they see how awesome it looks. The “Like This” image above has the right amount of fabric to pinch.
Length
The shirt should end somewhere between upper to mid crotch. I would rather it be closer to mid-crotch than upper-crotch because this avoids showing stomach when reaching up for things and allows it to be lightly tucked into the front of your belt/pants to break up your proportions – if you want.
Tails
Luckily, most designers are getting rid of tails, because I don’t really like them anyways. But if you have a polo shirt that has a tail, make sure the back part is no more than 2 inches longer than the front. Even then, I’d advise you to get a polo without a tail, because 99.9% it doesn’t look so great.
If you live in a climate where the temperatures drop during the winter, you’re going to need a coat or two. So let’s talk about Overcoats & Peacoats. They’re not to be confused with a jacket or windbreaker or whatever other sorry excuse for a coat I see guys wearing during the winter months. You need a proper coat that’ll look sharp and timeless and last many, many seasons. Your coat is the first thing anyone is going to see (aside from your shoes and a scarf) during the winter months, so let’s make sure you look amazing.
Common Overcoat & Peacoat Mistakes
In my travels, I see a lot of Overcoat blunders, so let me go over the common mistakes I see guys making with their coats before we dig in.
Too Boxy This makes stocky men look really wide and/or short and thin guys look even thinner.
Too Long This would technically fall under fit, but it’s such a big problem that it deserves it’s own section. Your overcoat is designed to go over your clothing, not be a blanket you threw over yourself! The worst is when I see guy’s sleeves going past the beginnings of their palms or their coats hitting mid-shin. If a coat goes past your knees, it’s going to collect dirt, mud and salt stains on the bottom – gross!
Too Complicated Some of my male friends suffer from this: They just have too much stuff going on with their coats. As I mentioned in my first #AskAW episode, you don’t need epaulettes/shoulder straps, sewn in sweaters or hoodies or a bunch of pockets or zippers or… things hanging off your coat. It looks cheap and tacky.
Too Trendy Even though I work in the fashion industry and attend the various Fashion Weeks around the world, good lord, there’s some jackets I see guys wearing on the street and I just wonder what happens once it goes out of style in a few weeks. I would never recommend something trendy as a Men’s Wardrobe Essential because you’ll probably only get one winter’s worth of wear out of it.
Not Appropriate For the Climate If you live in a warmer climate and are wearing a long overcoat without a suit, you look silly. There’s a time and a place for everything and it’s important to understand this in all things, but definitely in regards to coats. See below for details on when it is or isn’t appropriate to wear your coat.
A man should own at least one of these two coats, maybe both. See below to determine whether you need one or both coats in your closet.
Overcoat
There’s two factors to determine whether you should own an overcoat:
Does it snow where you live? An overcoat is an essential if it snows where you live because it’ll cover more of your body and be a great coat to layer clothing under to keep warm on the colder days.
Do you wear suits often? If you wear suits (like a gray suit), regardless of your climate, you need an overcoat because this is the only coat that compliments a suit. A Peacoat won’t work with a suit because (if it fits properly) it’s too short to cover a blazer or suit jacket as well as too casual for this type of outfit.
Peacoat
Every guy, regardless of his climate or whether he wears suits regularly or not, should own a Peacoat because it’s great for casual outfits in your Essential Wardrobe. If you live in a colder climate, it’s also great for warmer winter days and through the early parts of Spring. Notice I’m leaving out Fall. This is because that’s when a Blazer, Leather Jacket and Harrington Jacket really shine. For moderate/warmer climates, like Southern California, a Peacoat will be your “winter” coat.
Double-Breasted or Single-Breasted Coats?
A proper Peacoat is always double-breasted, so that’s not an issue.
As for Overcoats, stick to a single breasted coat because a double breasted Overcoat would require you to wear it buttoned 24/7 since it looks really big and floppy when it’s left unbuttoned. Single breasted gives you the option to wear it buttoned or unbuttoned while still looking sharp and form-fitting.
The Best Overcoat & Peacoat Colors For Men
For Peacoats, you want to go with the classic Navy color. For Overcoats, you can go with Navy, Camel (tan), Black or Dark Gray. If this is your first Overcoat, go with Dark Gray or Black. If it’s your second, get a Camel Overcoat to inject some color into your wardrobe, as it’s still a neutral color that will go with the rest of the Men’s Wardrobe Essentials.
I chose these coats because they all have a great tailored fit and the material, coat length, lapel width, buttons and the overall construction of them is impeccable. I love the Brooks Brothers charcoal Overcoat, which I actually used on a recent shoot with Harrison Ford, and I was amazed at how well-designed this coat was. The Burberry and Billy Reid Peacoats are my favorite Peacoats of all time! The details are incredible and they’re flattering on every man. An interesting fact: The Billy Reid coat is named the “Bond” coat because it’s the exact one Daniel Craig wore in “Skyfall.” The Burberry runs on the slimmer and slightly longer side, so if you have a shorter and wider build, then this may not work for you, although my model (below) was wearing it and he was quite “built”, so YMMV (your mileage may vary).
Each of these coats has a simple and clean design with no unnecessary flourishes, which you’ll usually find with cheaper alternatives. The price point is great for these considering they’re wool and wool-blended coats and will keep you warm and looking sharp. I love the Topman Camel Overcoat a lot, which is why I used it on my model below!
$198 – 
$480 – 
$1,455- 
$760 – 
$698 – 
$575 –
$165 – 
$2,000 – 
$90 – 
$150 – 
$295 – 
$280 – 
$325 – 
