- Boots and Shoes
- Coats & Jackets
- Shirts & Sweaters
- And various Accessories
Like always, I only recommend products that I’ve personally touched and worked with – in all budget ranges. I’m fortunate in that I get to touch hundreds of menswear items a week, so when I say something is great, it’s not because I got paid to sell you a bunch of cheap [email protected]*t like everyone else – it’s because I have actual experience with these items.
This series is a supplement to my Men’s Wardrobe Essentials Series. In that series, I covered the year-round essentials that you should have in your closet already. If you haven’t read/watched those articles and videos, do that first so we’re on the same page.
The Best Colors & Patterns For The Season
Since I don’t want to go over colors and matching them in every single video in this series, let’s talk about Fall and Winter colors and patterns and how to match them to your outfit and skin tone.
The appropriate colors for this time of year are:
- Mid to darker greens
- Shades of browns (camel to dark brown)
- Shades of blues (light chambray to navy)
- Shades of gray (light, medium and dark)
- Burgundy and wine colors
- Darker or “burnt” Orange
As for patterns, this is what I like to call “plaid season”. It’s the best time of year to wear plaid because its more visually heavy and pairs nicely with the heavier clothing you’ll be wearing, like sweaters, wool coats and wool trousers. For outerwear and Fall/Winter suiting, I love a good windowpane, as well.
HOW TO Match & wear COLORS BASED ON YOUR SKIN TONE
If you’re darker skinned, this is less of an issue because those colors look great on you. But if you’re pale or yellow-toned, this can be a disaster if you don’t know what you’re doing.
PALE or Yellow Skin
If you’re pale or yellow skin toned, make sure that your camel, burgundy, or burnt orange pieces are an outer layer and not a base layer. Let me show you what I mean.
You’ll notice in the below photo that I have my pale model wearing a camel sweater. But you’ll also hopefully notice that there is a white ring of a t-shirt sticking out from under the collar.
This is VERY important because that little sliver of white provides separation between the skin and sweater. The camel color would completely wash out his skin tone and make him look sickly if it wasn’t there. It’s much more apparent in person than images, too.
Below is the same model wearing a burnt orange sweater, but you’ll notice that I have a gray plaid shirt under the sweater to provide that necessary separation of the sweater from his skin. If that wasn’t there, the orange would bring out the pink tones in his skin – which would make him look red and flushed.
And lastly, going back to my white sneaker article/video, I styled my model in a burgundy bomber jacket with a black t-shirt. The shirt provides the necessary visual separation to not bring out the pink tones in his skin.
If I had him in a black jacket and burgundy t-shirt, instead, he would look oddly red-faced. This combination, though, would look awesome on someone with darker skin.
So to recap: If you have a pale or yellow skin tone and want to mix Fall/Winter colors into your wardrobe, just make sure it’s an outerwear piece with visible neutrals (white, grey, black, navy) underneath.
Now, if you’re darker skinned, you can still follow the pale/yellow skin rules above because it’s the classic way to wear color and looks good on everyone. So when in doubt, wear your statement color as outer layers. But with darker skin tones, you have the added advantage of being able to wear all these colors in your shirts and sweaters and then have neutral outer colors because the contrast looks great with your skin tone.
Here’s some examples of outfits that look great on darker/warmer skin tones that would look horrible on a guy with yellow or pale skin:
Just do me a favor, though. Don’t go overboard with color. Have one standout color in your outfit and then pair it with neutrals everywhere else. When you start throwing burgundys, greens, blues and browns all in one outfit, it’s just too much going on.
How To Wear PLAIDS AND PATTERNS
It’s a great time of year to incorporate them into your wardrobe. I prefer to keep the plaids to collared shirts because it looks good on everybody and is really hard to mess up. You can wear them on their own, with the sleeves rolled up, or throw on a nice solid colored sport coat, bomber or trucker jacket over it and the shirt will look great.
The key to wearing patterns is to make sure the rest of the items in your outfit – pants or jacket/sweater/coat are solid neutral colors. It’s when you start mixing patterns that’ll get you in trouble real quick.
So pick an item in your outfit (normally a shirt, sweater, jacket or coat) for a pattern and then have everything else be a solid color. And also make sure that just like with your ties and pocket squares, you want a color in your plaid to be a similar shade of one of the colors in your pants or jacket/sweater. Then you’ll have a nice, classy and cohesive look.
My Favorite COLOR COMBINATIONS For The Season
Here’s some color combinations I love and use with my clients during this time of year:
- Green and blue
- Gray and brown
- Blue and brown
- Burgundy and blue
- Burnt orange and blue
These are my go-to colors and if you stick to these combinations, you’ll look sharp and timeless during this season.
So without further adieu, let’s get into the Men’s Fall and Winter Essentials.
So here it is: These are the quintessential shoes that every man should have in his closet for year-round wear. Anything outside of these are specialty items, like snow boots, so they’re not included in this article.
Have questions? Curious what others think?
Join us in the comments section of the video above.
1. Athletic/Running Shoes
Buy the Nike Roshe FlyKnit in gray
There’s nothing better than a sleek pair of athletic shoes. Not only can they function as your gym shoes, but they can be worn with your casual outfits, as well.
I recommend sticking with a black/white, black/grey/white (like above), or navy/white color to ensure that your sneakers compliment all your outfits. Other crazy colors like neon green or a bright red will only draw attention away from your outfit which is why I’m not recommending those colors. You probably wouldn’t know it, but these shoes are one of my clients and almost a year old.
Since all of the shoes I’m recommending have white soles, I highly recommend Jason Markk’s Essential Shoe Cleaner Kit. Just give the soles a quick scrub with the included brush and soap every few weeks and they’ll look good-as-new for a long time.
2. White Sneakers
Buy the Adidas Stan Smith Sneakers
The second pair of shoes you should own, is what I’d consider an absolute essential to any well-dressed man’s wardrobe, which is why they were also included in my Men’s Wardrobe Essentials series.
They’re clean, classy and look great with a lot of your casual, even up to a little more dressy, outfits. Throw on a nice fitted blazer and some dark wash jeans with them and they’ll look amazing. See here for outfit inspiration images.
Under no circumstance should you wear these with a suit, though. That’s a trend that’s been floating around for a few years and I just think you’re not doing a suit justice by dumbing it down with sneakers.
A quick note, because it’s been brought up in the comments of my White Sneaker Video – Jordan’s and Air Force Ones are not the same as these – even if they’re white – because the shape and profile of those shoes are completely different. Notice how sleek and simple the profile of the above shoe is – THAT’S what makes all the difference. Jordan’s and Air Force Ones are chunky looking and have a very specific look that a lot of men can’t pull off.
3. Suede Driving Moccasins
The third pair of shoes you should own are suede driving moccasins. I’ve already covered these in my Summer Essentials Ebook, but they’re also great shoes during the other parts of the year, depending on your climate.
If you’ve never worn a pair, then you really should try them because they’re the most comfortable middle ground between a dress shoe and a sneaker and after they’ve been broken in a little bit, they’ll feel like you’re wearing a pair of socks.
I have these ones here by Tod’s that I really love. Stick with dark brown first, then you can add a tan color and then navy which will cover you for any outfit you can wear outside of a suit – which you should never wear driving mocs with. The construction is fantastic and they hug your feet nicely –
which is important because a lot of cheaply made driving mocs tend to look loose around your feet which is to be avoided.
There’s three things to remember about driving moccasins:
Only wear no-show socks with them. I did a whole video about socks so check out the link in the video description.
Before you wear them for the first time, make sure you Scotchguard them in order to protect the suede from dirt & liquids as much as possible.
They’re going to get dirty, it’s inevitable with suede. So buy them knowing they’re going to have a shorter shelf life than the rest of your shoes, but trust me, you won’t care because they’re so damn comfortable.
4. Oxford Or Derby Dress Shoes
The fourth pair of shoes you should own are Oxford or Derby dress shoe with a sleek profile and round toe. I’ve covered these extensively before, but every man needs at least a black and possibly brown pair of dress shoes in his wardrobe. They go well with all outfits outside of a super casual outfit (think: t-shirt and jeans). And since you should at least own one suit, these are necessary because you can’t get away with wearing any other shoes with your suit. Remember: the goal is to have you looking amazing, no matter the scenario or outfit.
I prefer plain toe, but you can also get cap toes, but I will grab a pair of plain toed Oxfords or Derbys over any other kind of dress shoe 99% of the time.
As for brogueing, burnished toes, oxblood or other unique colors, don’t get me wrong, I love them, but that’s like two levels down the road if you’re new to dressing better. They’re very specific and won’t go with a lot of your outfits, so grab them after you’ve invested in a classic black and dark brown oxford.
5. Brown Leather Boots
The final pair of shoes – in this case – boots you should own are a pair of brown leather boots.
They’re utilitarian in that you can wear them in a lot of adverse weather situations as well as in more elevated casual outfits. I prefer brown because boots are usually more geared toward the cooler months, and brown is a great fall/winter color and it goes AMAZINGLY well with the dark wash jeans and wool trousers you should already own. But don’t be mistaken, you can also wear these year-round.
It’s been asked this a few times by viewers, so unless you’re going for the lumberjack or American/Japanese worker-style look, don’t wear these boots with a suit because these ARE NOT DRESS BOOTS.
I love the pebbled brown leather and goodyear welting of the Purdey boots above, which is why they’re my top choice. Trust me, I spent a lot of time finding the best boots out there and these are hands down my favorite.
If you want to know how to tie your boots properly like this so don’t have a bunch of excess laces flopping around, check out my video about how to properly tie men’s shoelaces.
O’Keefe Algy Split-Toe Weatherproof Pebble-Grain Leather Boots
Crockett & Jones Islay Wingtip Boot
Frye Jones Lace Up Boots
Lots of readers/viewers have been asking me to do an article and video about how to roll or cuff men’s pants, so I’m finally doing it! The article is great and all, but the act of rolling your pants is not something easily shown in still images, so do yourself a favor and watch the video below for the fully experience.
With the exception of jeans and boots, you should only be rolling your pants in the spring and summer, unless you’re in a climate where it’s warm all year-round. This is very much a warm weather flair to add to your dark wash jeans, chinos or khakis or even wool pants and trousers. But it is a little odd to wear during the colder, winter months.
How To Quickly Measure Cuff Width
Before we begin, let me show you a quick and dirty way to figure out the proper width of your cuff by using your finger joints. The each joint of your index finger is roughly an inch long.
So if you need the cuff width to be about 2″ wide, the top of the cuff would hit right around the second or middle joint, like in the picture below:
The Simple Cuff
This cuff works especially well with slim fit jeans. I like to use this cuff when I’m going for a cleaner, sleeker look with a client. I’d caution against using it with chinos or other pants, as the fabric can be a little floppy around the ankles.
You also want to avoid using this cuff if you’re wearing straight fit jeans because your ankles will be swimming in a bunch of fabric. Use the pinroll cuff in the next section, instead.
Before you start cuffing, you should already have your jeans and shoes on. Otherwise, it’s harder to tell what the finished product looks like and if you’re showing the right amount of ankle. Hopefully you’ve already seen my men’s jeans fit guide so you know that your slim fit jeans should have a slight break at the hem. This cuff won’t look right with any other type of pant break.
How to Cuff
Low Top Shoes
If you’re wearing low top shoes, roll up your jeans’ cuff once.
The cuff width should be between 1.5” to 2”. If you’re on the shorter side, get the cuff as close to 1.5″ as possible. If you’re on the taller side, go for 2″. This will maintain the proper promotions for your body type.
Make sure that the roll is the same width or thickness on the front and back of the pants before you do the second roll. After finishing the second roll, the bottom of the cuff should just hit the top of your outer or inner ankle bone, like in the image below:
Boots or High Top Shoes
It’s the same as low tops: do at least 2 rolls and make sure to maintain the 1.5″ to 2″ cuff width, depending on your height.
The bottom of the cuff should either lightly graze the top of the shoe or boot or go a little bit past the top of the boot or high top. The image below, has the pants rolled up 3 times on the left and 2 times on the right. Both are equally acceptable lengths. I prefer 2 rolls, as 3 makes it look a little too military for my tastes, but 3 is just fine if that’s what you prefer.
The Pinroll Cuff
Again, start with your pants and shoes already on. Check my men’s jeans fit guide and chino pant fit guide for details about the type of break your pants should have before cuffing. If your pants aren’t fitting properly or they’re too long at the hem, the roll will look big and chunky around your ankle, which you don’t want.
How to Cuff
Low Top & High Top Shoes and Boots
With your thumb still holding the fold against your ankle, start rolling the cuff up with both hands. Make sure the roll is between 1 to 2 inches wide. If you’re on the shorter side, keep it around 1″ and go closer to 2″ wide if you’re taller. This will maintain the proper proportions for your stature.
if you’re wearing low tops, you want the bottom of the cuff to hit around 1.5 to 2” above your outer ankle bone, like the image below. If you need to roll 3 times to get there, do that.
The only exception to the 3 roll maximum is if you’re wearing boots or high tops. Then you need the cuff to just cover the top of your boot or lightly graze the top of your high tops when standing up. The image below has the cuffs rolled twice.
That’s it! Now cuff all the things!
I’ll just cut right to the chase – there’s really only 2 good ways for how to roll up sleeves. Do one of these and never think about it ever again.
A quick note:
The images for how to roll up your sleeves below are from Esquire, whom I love and work with, but they’re rolling their shirt sleeves above the elbow. You should NEVER do this, because, while it looks great in pictures, it usually looks like the image to the left in person – lumpy and just, not good. It will never look as good as the pictures, I promise you.
The Basic Roll
- Unbutton both buttons of the cuff. If there’s a button in the mid-forearm area, unbutton that one too.
- Flip the cuff over. Your cuff will dictate the width of your roll. If you have a stiff cuff, normally found on dress shirts, do not fold the cuff in half to make a slimmer roll. It will ruin that shirt’s cuff forever. If it’s not stiff, like with an Oxford button down dress shirt, then you can fold it in half for a less wide roll, although I wouldn’t advise doing a half roll. It usually looks better with the full cuff.
- Roll it again, and again, and one more time so that the top of the roll should stop just below the elbow, or mid to upper forearm (see the video for details).
- If you go above the elbow, the roll starts to get really bulky and it’s just not a good look. As a woman, I love when the shirt cuff hugs the muscular part of the forearm. It looks very… raaaaawwrrr!
The Italian Roll AKA The GQ Roll
- Unbutton both buttons of the cuff. If there’s a button in the mid-forearm area, unbutton that one too.
- Fold the sleeve up, so the entire cuff is an inch or so above your elbow.
- Next, roll your sleeves up onto the cuff, using your thumb to sort of tuck in the shirt into the roll, but still allow a little bit of the cuff to be exposed at the top.
- The top of the roll should hit just below the elbow, by about half an inch. Then you hopefully have about an inch of shirt cuff exposed above the elbow.
I see a lot of articles and videos about all the possible ways of tying a scarf, but honestly they’re mostly useless, ugly or both! So these are the 4 best ways for how to tie scarves for men and how I tie scarfs on my clients for cold weather events or publications like GQ & Esquire. Throw out all the other ways to tie scarves, they’re a waste of time!
A quick, note about length, material and patterns
This and socks is one of the few places where you really can’t go wrong with any choice. So I always tell my clients to have at it and choose anything they think looks great, it’s a perfect way to show off your personality. So any colors, patterns, materials and lengths that you like, go for it! You can’t go wrong here.
Here’s the 4 best ways for a man to tie his scarf.
This way of wearing a scarf is perfect for those who don’t like anything wrapped around their neck but still want to keep warm. I like it because it’s easy to do and it looks nice. It doesn’t do too much to keep the front of your neck warm, but it does keep the back of your neck as well as the side of your coat nice and insulated.
Definitely wear this underneath your jacket or coat, it’ll keep it in place. Otherwise, it’ll move around a lot as you walk.
- Take the two ends of the scarf, have them hang equal length on either side of your neck.
- Now simply tuck in each side of the scarf under each lapel of your jacket or coat. It seals in the small gaps between your chest and coat to keep you nice and warm.
It’s a pretty standard way of wearing a scarf. You probably wore yours like this as a kid and it’s just fine for men. It’ll do what The Drape won’t do – keep the front of your neck warm.
- Start by putting the scarf behind your head and lowering one side to be twice as long as the other.
- Now wrap the longer side once around your head. The ends can be equally long or uneven. It doesn’t matter.
- Tuck the excess under your collar or lapel, if you want.
This is my absolute favorite way to tie a scarf on a man and the warmest way to tie a scarf. When I see men on the street wearing a scarf like this, I think it just looks so damn sharp! You can’t go wrong with this way of tying a scarf.
- Fold the scarf in half.
- Wrap it around the back of your neck.
- Tuck the loose ends through the loop created by the other side of the scarf.
- Adjust to desired tightness.
This way of tying a scarf tends to look best with longer scarves, but you can get away with it if you’re using a shorter one, too.
- Put the scarf around your neck, making both sides equal in length.
- Cross the two ends.
- Push one side up and under the other.
- Pull it tight (but not too tight—breathing is important even in winter!)
That’s it! Those are the best (and only) ways for a man to tie a scarf.