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.
Boots are a fall/winter staple and the right pair (or two) should be versatile enough for a variety of outfits and occasions. I think Chelsea boots are more of a spring/summer style so we’re focusing on shoes that will get you through the colder, wetter months of the year and work better with heavier clothing.
One thing to remember, look at boots as an investment, good ones aren’t cheap, but properly taken care of they can last you many years. There are a ton of options out there and we’ll include our picks, but we’ve narrowed it down to three basic styles that you should have in your closet.
Desert/Chukka Boots
The most versatile and least seasonal, you can wear these nearly year round. They’re light and comfortable and work well with both casual looks (jeans, chinos) and more dressy looks (with sweaters and blazers).
What you probably think of when you think of boots, these are more rugged and have thicker/chunkier soles. The look great with jeans and chinos and will get you through the colder months and weather with ease. They can come in a variety of styles, some very casual, others a bit more dressy.
Yes, you can and should dress up your boots. Just make sure you’ve got the right styles. Think of these like the hightop versions of your dress shoes. They should have a thinner, dressier sole and nice leather. Look for them in cap toe or wingtip versions. Formality note: some dressier styles come with a bit more tread (called a lug sole) which can still look good with dressier clothes, but it will make them slightly less formal.
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.
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.
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.
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.
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:
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!)
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.
If you own any of the collared shirts I recommend in my Men’s Wardrobe Essentials Series, specifically the Oxford Button Down Shirt and a Semi Spread Collar dress shirt, you need to own some crew and v-neck undershirts. And before we get into it, there’s no scenario when you should ever wear a tank-top undershirt, AKA a wife beater – ever. You’ll see the lines underneath any shirt you’re wearing, and it just looks terrible. So let’s talk about the best undershirts for men and why you should own them.
Undershirts are essential because
They provide a barrier between your sweaty, oily, deodorant-riddled skin and your dress shirts.
Due to this barrier, you may not have to get them cleaned as often, which will prolong their life.
They make dress shirts, specifically light-colored ones, look much better by not showing your skin and/or nipples through them.
They add another layer to your outfit for a little extra warmth or moisture wicking – depending on the weather.
How to Wear an Undershirt Under a Dress Shirt
You would think this is simple, right? Me too, but it’s very rare when a client knows how to wear an undershirt properly. A good undershirt is not something anyone should ever notice. If it’s noticeable, you’ve failed.
These are the 2 rules for wearing an undershirt:
If you’re wearing a collared shirt without a tie, with the top button or two open, you need to wear a v-neck undershirt. Remember, no one should ever see your undershirt – even a bit of the collar.
If you’re wearing a tie, you have to wear a crew neck undershirt. Otherwise, you’ll be able to see the v under the shirt and it looks like crap.
When should you go without an undershirt?
The only time I’d suggest not wearing an undershirt is if you’re wearing a white collared shirt. If you’re a lighter skinned guy, this is more geared toward you. Because most other undershirts might be seen through. But you can still try wearing a nude or gray undershirt to see if it’s not visible.
This problem isn’t as bad if you’re darker-skinned and wearing a similar-colored undershirt. That said, if you have darker nipples or nipples that tend to stick out a little bit, then an undershirt is required for you no matter what. Just make sure it matches your skin tone relatively closely.
Are Undershirts Supposed to be Tight?
A lot of my clients ask this question and the short answer is: Sort of.
They shouldn’t be skin tight, but they should absolutely fit close to the body. Ideally, you want an undershirt to fit this way in the body and sleeves so you don’t see wrinkles or creases underneath your shirt. If the sleeves or body is loose, you’ll definitely see the line under the sleeves and wrinkles in the body – no matter the color of shirt you’re wearing over it.
Are Undershirts Supposed to be Thin?
Yes! They should be thin because they’re an underlayer and a thinner shirt will feel better and not add bulk to your frame. You don’t want this to happen regardless of your body type.
Should I have only white undershirts?
Not necessarily. I always have my clients wear undershirts that are closer to their skin tone. So if you’re darker skinned, you can go with a darker gray, brown, or black undershirt. Lighter skinned men should stick with light gray or white. A warning though, if you’re lighter skinned: a light gray undershirt under white or light-colored shirts is ok, but honestly, I’ve tried this a few times it and it tends to make the dress shirt look dingy or kind of faded. It’s not a good look, so I usually say to go without an undershirt in these instances.
Another quick note while we’re talking about white undershirts
I see this often with guys – if I can see exactly where your undershirt starts and ends around your neck or sleeves, (this only happens with light blue and white collared shirts), this means your shirt’s fabric is too thin and/or you need to change the color of your undershirt to match your skin tone better.
The Best White and colored Undershirts
These are the best undershirts that my clients and I love the most. Having tried all the major ones out there, these are my favorites:
Second Skin Crew and Deep V-Neck undershirts are my favorites. I like these a lot because they fit snugly on all body types and the fabric is super soft and has a little bit of stretch to it, so they won’t leave winkles showing through your shirts. But these niceties don’t come cheaply. Unlike their underwear, though, which I discussed here, they are very durable and will last you a good long while. They also make a nude and black colored undershirts to cover most men out there.
A quick note about their V-necks. Their images aren’t quite accurate and their titles are misleading.
Their “Deep V-Neck” is actually a regular v-neck length, so get that one and don’t waste your time with the regular v-neck, because the regular one is way too high and will absolutely be visible if you wear your collared shirts unbuttoned. I know the pictures look like the v is quite deep, but trust me, in person they’re not that deep.
RibbedTee makes some of the softest, most comfortable undershirts I’ve tested. My clients said it was like wearing a soft fluffy layer of air. Their gray undershirts are great for lighter skinned guys, too, but they make many colors. You honestly can’t go wrong with any of their undershirts, but my clients were partial to the Tri Blend, Supima cotton and their Evo Tencell ones.
For a budget-friendly option, I really like Calvin Klein’s Cotton Classic undershirts because the fit is great and the fabric is not too thick or thin, which is a problem with most other undershirts in this price range.
I like them because they also have different fits based on your body type – like slim and regular – which fit my larger or taller clients very well. They also make a similar undershirt to Tommy John called Body Modal, but I say just spend the few extra bucks and get the Tommy Johns instead because they’re just all around better.
I mentioned these in one of my AskAW videos because my clients who wear these LOVE them. If you’re looking to slim down your waist, belly or chest area, these are perfect. I like to say that they are like visual airbrushing tools. They’re not so snug that it feels like you can’t breath, which is important because I think a lot of men assume they’ll be too restrictive, but they’re just a little bit tighter than your average shirt, but they will literally drop you down a waist or shirt size in most cases.
Alright, that’s it. Those are the best undershirts for men – period!
Chino pants should be a staple in every man’s wardrobe. They are among the most versatile of men’s pants—they look great with a t-shirt, a sweater and button-down, or can be dressed up for a business casual event. They’re the perfect alternative to jeans since they are more comfortable and breathe easier. This is especially true in warmer weather due to the soft, worn-in cotton twill fabric that breathes easier than denim. And when you want to inject some color into your wardrobe, chinos provide an excellent avenue for this.
The Chino Pants Rules Most Guys Break
I see a boatload of guys making the following mistakes, so I want you to be aware of them:
Do not wear or own black chino pants. You’ll look like a waiter or valet guy.
Chinos are not dress pants or trousers. They’re the middle ground between casual and formal and should not be worn for anything above a business casual event.
Chinos should be worn with a quarter or no break. They can even be worn at ankle length in some cases, but never, ever longer than a quarter break.
Chino pants do not have extra pockets on the legs, hammer loops, stitching, etc. Those aren’t chinos, no matter what their name says.
Don’t wear pleated chinos. See the pleats section below for an explanation of why you should never wear them.
Pressed creases on the legs are the devil’s work. Don’t ever buy them like this or add them yourself.
The same goes for pre-cuffed hems. Don’t wear them, please. You can roll the cuff later on, but don’t buy the ones that come pre-cuffed.
To see more style mistakes that men make and how to fix them, click here.
What are Chinos?
The word “chino” means “toasted” and is derived from Latin American Spanish. Chino pants are named after the cotton twill fabric they’re constructed from, often called Chino Cloth. Another distinguishing characteristic is that chino pants will also usually have side-loading pockets, which are different than the traditional front or top-loading pockets as traditionally found on jeans.
Khaki vs Chino
In the most simple terms possible: Khaki is a shade of brown. Chino is a type of pants and called this because they’re usually made from Chino cloth.
The original khaki (light brown) is the traditional and most popular color, but chinos are come in many shades. See my color preferences for men below.
I don’t care how old or young you are or what your body type is – whether you’re thin or a larger guy, you should NEVER, EVER have pleated chino pants. Honestly, I f*#@%ing hate them because they’re so unnecessary and are unflattering on every guy. I’ll be the first to dance on their grave if they ever completely go away. I’ve never seen a guy look good while wearing them – ever.
To Cuff & Crease or Not
You can, and sometimes should, cuff or roll up chino pants. But don’t ever buy a pair of chinos that are pre-cuffed. It’ll be very hard to get that crease out and the hem will likely be very thick, which won’t look that great.
As for creasing the front the of leg, if you’re looking at a pair of chinos that’s creased like this, run for the hills! They should never be creased like dress pants because… repeat after me: They’re not dress pants.
What colors should you get?
You should at least have two colors of chinos because they’ll pair well with all the other items in your Essential Wardrobe. A quick note about colors: Whatever you do, make sure the colors you choose are not too shiny or glossy looking. You’ll know it when you see it. You want a more matte finish to your chinos.
Sand – I prefer this lighter brown/tan color than the darker, flatter khaki color. Some brands will call sand colored pants khaki, so just go for lighter brown colors regardless of what the brand calls them. The model in the image at the top of this article is wearing, what I’d consider, the perfect sand color. Shoot for something similar.
Navy – Whatever you do, just don’t get such a dark navy that it looks black. That’s a big no-no. The navy in my first “Best Ways To Wear” image below is what I’m talking about.
If you already own these colors and want to add more, then go for gray/charcoal or an olive color. If you want to try other colors, just make sure you understand what colors work best with your skin tone.
The Best Chino Pants For Your Body Type
Slim or Regular Build
You’ll want to get a “Slim” fit chino pant that will hug the thighs, knees, and calves while tapering down from your knee to ankle.
A lot of my slim & regular built clients initially believe this style will make them look too skinny. This couldn’t be further from the truth. It’s just that they’re used to wearing super baggier clothes to try and hide their slimness, which, coincidentally, just makes them look slimmer. A proper fitting pair of chino pants just looks right, regardless of your build, and doesn’t make you look one way or another – I promise.
Determining the ideal cut of your chinos depends on your physique.
If you’re a heftier guy or have larger thighs, I recommend a straight leg chino. It will give your body a trim, well-proportioned appearance. Slim fit chinos that taper slightly in the leg will make you look somewhat imbalanced—giving you a top-heavy look with skinny legs. Unless you’re on the shorter side, then a slight taper is OK, but under no other circumstances should your chinos be tapered.
Larger Build
The classic “Straight-Leg” fit is perfect for you. No matter a man’s build, but especially in your case, it’s all about balancing your body’s proportions to make sure your bottom half complements your upper half. So stick to this cut of chinos for your physique and you’ll look fantastic.
I’m a huge fan of each of these designer’s chinos as the construction, quality, and fit are spot on. You won’t go wrong with any of these, but just remember to choose the right fit for your body type.
If you’re on a budget, all three of these are great. Each brand offers a few color choices, which are usually the typical khaki, navy, and gray. A great thing about Uniqlo is that they offer free hemming service so there’s no excuse to have your chinos be too long 🙂
The casualness of a chambray combined with the sharpness of a sport coat is a guaranteed to turn heads in the office or at any wedding. Wear an indigo button-down chambray shirt, a grey wool sportcoat, blue chinos, and black oxford dress shoes. Spice things up with a lively pocket square and a simple plaque buckle belt.
This post is part of my Men’s Wardrobe Essentials Series. In the series, I give my tried-and-true men’s wardrobe essentials/basics/must haves that every guy, whether a teenager, in their 20’s, 30’s and well past their 50’s should own in order to be a classic, stylish, well-dressed man.
For well over 70 years, leather jackets have represented individuality and a rebellious, manly side throughout American history. Marlon Brando, The Ramones, WWII fighter pilots, and Springsteen all come to mind when I think of leather jackets. A well-made leather jacket is an essential addition to a man’s wardrobe because it will never go out of style, can be dressed up or down, will generally last a lifetime and fit like a second skin.
Watching a man put on a leather jacket is like watching a prize-fighter standing over his opponent after he’s been knocked down. There’s just something about it that harkens back to a classic, badass, bygone era.
What Type Of Leather Jacket Is Right For You?
There are many different types of leather jackets available, some better than others. The biker jacket, what Marlon Brando is known for, is what usually comes to mind when thinking about a leather jacket. As iconic as this jacket is, I don’t recommend it for most guys. The buckle straps, zippered cuffs, and buttoned collar and lapels are a bit much in my opinion. Unless you’re going for the ’50’s greaser or heroin-chic rockstar look, it’s best not to go this route. It often looks much better in print or on the screen than it does in person.
If you like the classic ruggedness of the biker jacket but want a cleaned-up version, the motocross jacket is perfect for you. It has a tabbed collar and less… stuff all over it, which makes it much more versatile. I prefer this style over the biker jacket because the clean design won’t add additional bulk to your frame, so it’s a great choice for all body shapes.
My hands-down favorite of all leather jackets is the bomber style jacket. It has a clean, timeless body style and the elastic, ribbed cuffs, collar, and waist allow the jacket to hug your body nicely, while adding more comfort than the more traditional styles. The leather on these jackets is usually very soft and supple compared to the other styles, so it makes for a perfect everyday type of jacket.
Best Ways To Wear It
The Biker Jacket
If you go the biker jacket route, I highly recommend this AllSaints ‘Conroy’ leather biker jacket ($670). It has all the classic biker details and an awesome slim fit, which is important since you don’t want it to add bulk to your frame. I’ve personally worked with this jacket, and like all of AllSaint’s leathers, the quality and attention to detail is exceptional. The jacket a steal at this price.
Going on a date? Pair with a white button-up shirt, wool trousers, and lace-up leather shoes and watch her salivate the whole night. Switch out the dress shirt with your favorite t-shirt and a pair of dark washed jeans for beers with the guys.
Allsaints – Leather Biker Jacket
Burberry – Leather Biker Jacket
H&M – Leather Biker Jacket
The Motocross Jacket
I’m recommending this Zara jacket for its awesome fit, super clean design, and perfect cognac shade of brown. You may be wondering why it costs less than $100. That’s because this is actually a synthetic leather jacket. But I can assure you, no one will notice. If anything, this jacket is softer, both in feel and in the hit to your bank account than real leather, which is a plus in my book. A brown jacket pairs well with shades of blues, so go with a light blue striped dress shirt, solid navy tie, light brown v-neck sweater, and a pair of dark jeans and brown dress boots to pull this awesome look off. Nix the v-neck sweater if it’s a little warm out or you tend to run warm-blooded.
Allsaints – Leather Biker Jacket
Schott Cafe Racer
The Bomber Jacket
If you want something that looks great, is super versatile as well as comfortable, then look no further than the bomber jacket. Whether going out at night or running errands during the day, I’d pair this jacket with a white t-shirt, charcoal or dark brown wool trousers, and lace-up black leather boots. You’ll look put together and not like you’re trying too hard.
Allsaints – Leather Bomber Jacket
Burberry – Lambskin Bomber Jacket
Final Thoughts
In my opinion, a well-made leather jacket is an essential addition to a man’s wardrobe because it will never go out of style, can be dressed up or down, will generally last a lifetime and fit like a second skin. When you throw one on, like a well-tailored suit, it’ll make you feel and look better. You’re not just investing in a leather jacket. You’re investing in yourself. Remember that and let’s see those leather jackets!
