Because of all the rain that’s been happening here in LA and the East Coast, I’ve been trying to find stylish yet practical jackets for some of my clients who are doing press right now along the soggy coasts. I found this awesome snokel jacket that fit the bill perfectly.
I was so excited to find a lightweight snorkel jacket that fit the bill perfectly. A snorkel jacket is basically a parka. It’s a 3/4 length jacket hitting mid-thigh and has a drawstring hood that can tighten so your entire face is covered except a small breathing hole, hence the name snorkel. A lightweight jacket, like the one in the image, will also take you through Spring and is easy to layer under.
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.
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.
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.
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.
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.
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.
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.
Crockett And Jones Galway 2 Apron-Toe Boot
John Lobb Alder Boots
Frye Jones Lace Up Boots
Red Wing for Brooks Brothers 4556 Iron Ranger Boots
This article & video is part of the Celebrity Style Inspiration Series, where Antonio Centeno from RealMenRealStyle.com and I pick out great outfits from actors from movies and tv shows and demonstrate how to recreate and incorporate them into your wardrobe.
In the other video/article, currently live on RMRS Channel & Website, we talked about Steven Yeun’s style from The Walking Dead, but I don’t think a lot of people know that Steven’s off-screen style is also very, very good. He’s one of the few male celebrities that I know who doesn’t use a stylist who looks amazing all the time. I’ve worked with him quite a few times over the years and he’s definitely one of the naturally best dressers I know – and a total sweetheart!
When I was deciding on which of his outfits to feature, I found this one from a red carpet appearance and loved it, so I texted to let him know that I was going to do a video about it. He said he was excited to see how I’d recreate it, so… Hi Steven!
Below is Steven’s outfit I’m going to recreate for you. I specifically like this because it’s casual but has just the right blend of edginess to it with the boots and cuffed pants.
The Jacket & Sweater
I like Steven’s cardigan jacket a lot, but I prefer a bomber-style jacket instead (in my model image below) because not only does it look great on all body types, it also helps break up the top and bottom halves a little bit more with the black waistband, which also lends itself well to the cuffed pant and chelsea boot look. I had my model wear a plain white t-shirt underneath the sweater because it provides an extra layer of warmth and adds a nice little neutral accent just peeking through.
Pants and Shoes
I added some dark wash jeans to stay true to the outfit and even though suede shoes are not my preference for most men, I went with similar suede boots because they work very well in Steven’s outfit. I especially love my choice because it’s a nice dark brown suede, which is easier to wear than a more reddish-oxblood brown or a lighter brown like Steven’s boots. My color choice will also look a little cleaner longer since it won’t show as many stains.
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
This cuff is great for any cut of jeans, as well as chinos. I like this roll because it eliminates the issue of your pants swimming around your ankles when they’re cuffed.
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
To start, pinch the fabric on the inside of your ankle so it feels slightly snug against your leg or ankle.
Now fold the fabric over towards your heel. The reason why we do this is because it hides the fold better than if you folded the fabric towards the front.
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.
Now roll up the cuff a second time. You want to roll at least twice to make sure that excess fabric that we folded over won’t come undone. It won’t stay with just one roll.
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.
A plain, short sleeved t-shirt is an essential because they’re super comfortable, timeless, and everyone wears them. Now whether you need a crew neck or v-neck t-shirt is dependent on a few factors that I’ll get into later on in this article.
If you’re like most of my clients, you’re probably wearing a t-shirt or polo shirt most of the time, so let’s make sure you look amazing in them. Before we get into that, though, I have a few bones to pick with men in regards to their t-shirts. They completely crap the bed in a few ways:
Their shirts are full of logos.
They don’t fit properly.
The fabric is too thin, shiny, or worn out.
A horrible combination of the above.
Types of T-Shirts For Men
A t-shirt is defined as:
A lightweight shirt without buttons, with short sleeves and no collar. Often made of cotton and frequently bears a picture or slogan.
Before we get into the finer points of t-shirts, let’s talk about the two different types, first. Before I started in the fashion industry, I didn’t know that there were only really two types of t-shirts. So let’s quickly get this out of the way.
These t-shirts have round collars that fit closely to the neck like the image above. You probably have these in your closet right now. They are great base items for layering or worn on their own. They work on most body types. See the below section about fit for more details.
If your powers of deduction are strong, you’ll already know that the v-neck t-shirt is named as such because the neck is in the shape of a “v”. They also work on most body types. See the below section about fit for more details.
Long-sleeved shirts are not technially t-shirts. I put this here, because when I was first starting out, I swore that long-sleeved shirts, like Henleys, were also t-shirts. But, they’re not. Also, in my professional opinion you shouldn’t really own any long sleeve shirts. Henleys would be the only exception, but they only look good on certain body types. I’ll do an article about Henley shirts at a later time. But I don’t consider them a wardrobe essential.
I discussed my hatred of logos in my polo shirt article. And it definitely applies to t-shirts. Maybe more-so.
No self-respecting man should ever wear t-shirts with logos plastered all over them. We have enough billboards and advertisements in our lives, don’t turn your body into another one. Sports teams and concert/band tees are fine if worn to an event where it’s appropriate. But the worst is when I see guys wearing “designer” t-shirts. It just screams sucker, amateur and douche. Just don’t do it. If you own any of these, either throw them out right now or
How T-Shirts Should Fit
See the T-Shirt Fit Guide for details. But I’ll quickly mention here, too, that no matter your age or body type, a t-shirt (any shirt, for that matter) should have a trim fit and lightly hug your body.
That doesn’t mean it should be skin tight, but it also doesn’t mean it should be baggy, either. A lot of my clients with larger builds tend to think that their shirts need to be baggy to hide their imperfections, but it actually works counter to that. It’ll highlight your imperfections if you attempt to hide them under larger swaths of fabric. And if you’re thinner, a larger shirt won’t add any bulk to your frame, it’ll just make you look even skinnier.
I can’t tell you how many nipples and belly buttons I see walking around town because guys are wearing undershirts or flimsy shirts with really thin or delicate fabrics as regular t-shirts.
I see a lot of guys wearing what looks like white undershirts because the fabric is so thin. I’ve honestly been searching for months for good white shirts that don’t show skin through. See my recommendations below. Thin shirts/undershirts are not the same as regular t-shirts. Undershirts, true to their name, should only be worn underneath another shirt – usually an Oxford Button Down Dress Shirt or a Semi-Spread Collar Dress Shirt. They’re thin and soft because they’re purpose-built to go underneath something else.
Silky or Shiny appearance
The quickest way to look like a creepy uncle is to wear a shiny or silky t-shirt. You should only wear cotton and matte (not shiny) t-shirts. Nothing else.
Distressed or Worn out
Your t-shirts shouldn’t look like the garment equivalent of those terrible worn-out baseball caps. A t-shirt should look clean, comfortable and relatively new. Once they’ve got holes or they’re faded, even a little bit, they need to be replaced. Such is the nature of being a well-dressed gentleman. There’s nothing worse than old, stretched-out, or faded looking shirts, unless you’re deliberately going for that look.
You’ll get more usage out of your t-shirts if you wash in cold water and hang dry them. But once they’re stretched out or faded, it’s time to donate and replace them.
The Best T-Shirts For Men
Choosing the best t-shirts comes down to your body type, preference and the colors. I’ll reiterate again, because my older clients like to give me this excuse before they see the light: AGE DOESN’T FACTOR INTO WHAT SHIRTS YOU SHOULD GET – AT ALL.
Should I have V-Necks or Crew Necks?
Between the two, I would say it all depends on your preference. Some of my clients are adamant about their love or hate for one or the other. But if you don’t have a preference, I’d suggest getting one set of each. That way, you have the option to switch it up.
As for which ones you should get, there’s 3 points to consider:
If you have a longer neck, go with crew necks. A v-neck would visually lengthen your neck and make it look longer. Unless you can find shorter v-necks with a shorter “v” like the white shirt on my model below.
If you have a shorter neck, go with v-necks. It’ll make your neck appear a little longer.
If your neck is average, the t-shirt world is your oyster and you can have whatever you want!
What colors should I have?
Every man should have these colors to start since they’ll go with everything else in your Essential Wardrobe.
As for how many of each you should have, I suggest getting at least 2 of each, that way you can easily get through a week without needing to do laundry.
Best T-Shirts For Men
The fabrics of these options are really amazing and super comfortable. The James Perse ones are a personal favorite and I use them on a lot of my clients. I wish I could make all my clothes out of some of these materials. See my note in the section below, before making your decision. All of these shirts come in the colors I recommended above.
I’d probably default to these options over the designer ones because I find very minute differences between them. The biggest factors would be fit and slightly better fabrics. I don’t find the added costs are worth what you get in return, especially because t-shirts will need to be replaced much quicker than other items in your wardrobe. All of these shirts come in the colors I recommended above. I especially love the RibbedTee shirts and the American Apparel Summer Shirts.
All Saints White Figure Crew T-Shirt
Armani Exchange Grey Pima V-Neck Tee
Armani Exchange Black Pima Crew Tee
American Apparel Grey Tri-Blend Short Sleeve Track Shirt
American Apparel White Sheer Jersey Short Sleeve Summer T-Shirt
RibbedTee White Rex Cotton Modal Tee V-Neck 1-Pack