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.
In this article and video, I wanted to show you some of my favorite boots and shoes for this Fall & Winter. If you missed my big men’s Fall & Winter Essentials series, you should definitely check that out first, since this is more of a supplement to that instead of the other way around.
Suede Boots
Although you can certainly go with leather boots, I am a huge fan of these suede ones by Allen Edmonds. Everything from the superior construction, to the neutral taupe grey color, which I’ll often use in place of black or brown, easily makes this boot a winner in my eyes.
Another favorite of mine are these suede chukkas (aka desert boots) which lend a very Autumn feel to any outfit. Again, just like with the boots I mentioned before, you can certainly go with regular leather Chukka boots, as well. But I love these, specifically because they have a slim profile and a comfortable crepe sole which will feel like you’re wearing sneakers. Pair them with jeans or chinos for a put-together casual look.
Outside of white sneakers, grey is a Fall favorite of mine because it’s another neutral color that compliments the darker, more jewel-toned colors you’ll be wearing this season. You can go with suede, leather, or a fabric material, but just make sure to keep the design simple like these ones.
My articles and videos almost always center around a specific piece of clothing or accessory, so I thought it would be fun to switch it up and talk about 3 head-to-toe foundational outfits every guy needs. Once you have these 3 outfits, you can build an entire wardrobe around them. And here’s the beauty of them: from these 3 outfits, you can switch things in and out to add your own personal touch and truly make them your own.
Outfit 1
The first outfit is a casual one, comprised of a black polo shirt, a well-fitting pair of dark wash jeans and some white low top sneakers. This is a solid casual outfit that will always look great and put together on every man, regardless of your age or body type.
If you’re thin to average build, you can also wear a white t-shirt. However, if you’re a broader man that’s not in shape, and you decide to take off your jacket, then a white t-shirt will actually spotlight how big you are (and not in a good way). Also, the reason why you want to go with black chukkas is because black is the dominant color in your jacket. I went with leather chukka boots over suede and lace-up boots because the latter options won’t look appropriate for every season.
A bomber is a very stylish, modern alternative to a blazer that works in almost all the same occasions and looks great for every man, regardless if you’re a teenager all the way to a retiree. A younger gentlemen in high school or college, for instance, wouldn’t necessarily need a blazer, so that’s why I’m not recommending it over a blazer. If the occasion does call for a sport coat or blazer, in a pinch, you can use the jacket in my next recommendation and dress it up like I did in the picture below.
I love these two suits because it’s very easy to go formal by adding a tie or dress them down by forgoing a tie or swapping in a t-shirt instead of a collared shirt.
I came across this image that I thought would be a perfect Spring & Summer men’s suede jacket outfit because it’s a great, casual everyday outfit that you can wear when you’re going out with friends or if you work in a casual work environment. It has the added benefit of being able to be dressed slightly up or down as well as layered depending on the weather.
Jacket
A suede jacket is perfect for Spring and Summer and will look great on every guy, regardless of age or body type. But if you’re not into suede, or like other styles, look no further than the Harrington jacket or a wool bomber jacket.
The plaid shirt underneath the grey sweater can be switched out for your classic white or blue oxfords or other fun colors or patterns like navy and/or green plaid or gingham.
Let’s talk about my favorite and what I consider the best men’s dress shoes for Fall and Winter – Monk straps, Brogues, and Wingtips.
Quick note: Wingtips are technically Brogues, so I’ll be lumping them together throughout this article. Just know when I refer to Brogues that I also mean Wingtips.
I prefer these during the cooler parts of the year because they go much better with the heavier wool and cotton items you wear in your Fall and Winter outfits. Don’t get me wrong, they also work year-round, but I think there’s better options out there for the other parts of the year. Check out my Summer Essentials Ebook and Wardrobe Essentials Series for details about those options.
Below are the things I look for in a good pair of Monk Straps or Brogues.
MATERIAL
As I said in my Fall/Winter boots story, I love a good calf skin. Don’t get me wrong, I love a suede monk strap or brogue, as well, but if you live in an area with snow or rain, you’ll regret the day you wear them outside. So let’s wait to get into those until Spring or Summer.
SHAPE
I will say this about dress shoes until the day I die, but you want a nice, slim profile with a rounded toe box. Ain’t nobody got time for square or large, bulky toe boxes! – See the video near the top of the article if you’re unsure about what they look like.
COLOR
As for colors, I love a nice dark chocolaty brown, or even a medium brown, like a walnut. Black is also good, but the first color I’d get is brown because it goes better with all the Fall colors in your wardrobe. All these colors are represented in my suggestions at the bottom of this article.
SOLES
If you live somewhere with a bit of rain, ice or snow, then you can and should definitely have these with Dainite or rubber inset soles for added traction. If you don’t live in that kind of climate, then a regular leather bottom that you’ll find on 99% of dress shoes is perfectly acceptable, but I’d probably look for a Dainite or rubber insert sole as my default. There’s also lugged soles, which are pretty popular right now (and I included some in my selects below), but I have a feeling they won’t be around for the long haul. They’ve already come and gone with fashion a few times in my lifetime. When it comes to Fall/Winter boots, though, I love me a lugged sole.
MONK STRAP SPECIFICS
I prefer a double buckle because a single buckle looks less refined. (Example in the video at the top).
If you get black Monk Straps, make sure the buckle is silver, because gold or brass tends to look gaudy, but is perfectly fine on brown monks (examples in the video).
Also, please make sure the buckles are on the smaller side as opposed to some big ass buckles you’ll find on a colonial gentleman.
As for medallion toes and other flourishes, I like all of them, so check out my recommendations below.
These, to me, are the quintessential Brogue. If you’ve seen my other dress shoe article then you know my love of Allen Edmonds. They make amazing products with great value – and they don’t pay me to say that. I’m just a huge fan.
I love this color and the Dainite soles. They’re just perfection.
These hit all the points I look for in a double monk – the beautiful chocolaty brown with the matching soles, the silver hardware and the rubber tread inset for added traction. On top of that, they’re a GREAT price and my clients always comment about how comfortable they are. My other favorites are the Allen Edmonds Monks below, if you’re looking for something higher quality.
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.
In my Men’s Wardrobe Essentials Series, as well as my Summer Essentials Ebook, I touched on shoes a little bit, but the most-requested video/article for a while has been the number and type of shoes every man should own.
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.
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.
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.
Designer Options
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
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 🙂
