Fall and cooler weather will be here before you know it and it’s time to start thinking about transitioning your wardrobe. A key thing to think about with your fall wardrobe is changing temperatures, you want items that layer easily or can be versatile enough for varying temps. Like with the rest of the items in your Essential Wardrobe you want pieces that will have you looking sharp no matter your height, body shape, or age.
One quick note, while I love them, you’re not going to see henleys on this list because there are only a select few men that actually look good in them. We did an in-depth article on henleys previously and you can check out why I feel so strongly that only certain men can wear them.
Now, onto our picks for the Men’s Fall Style Essentials you need right now!
Denim Jacket
Classic, stylish and easy to layer, a denim jacket is a great pick for fall. Make sure the fit isn’t boxy – you want a slim fit. Also, we recommend a medium to light wash as they pair easily w your dark wash denim and with other go-to fall pants like chinos and corduroys.
I love these because of their casual vibe and versatility, they can function as an outerwear piece over a tee or be layered underneath something else (like that denim jacket we just mentioned) when it gets colder. Stick with solid colors like light grey, charcoal, black, dark green, and burgundy. You can go with cotton options or look for lightweight merino wool versions.
Yes, our love of bomber jackets is well documented, and for good reason, they look great on everyone. The softer, more textured material or wool or suede complements the Fall season.
We love a solid flannel or a check pattern and you definitely should have one or two of these in your closet to mix in with your wardrobe. These are great on their own or layered underneath a sweater or jacket or both if it’s chilly. Don’t forget: the length of the shirt should hit around mid-crotch/mid zipper. This allows you to wear untucked for a casual look or tucked in for a more polished look.
Some of our absolute favorite collared shirts come from The Tie Bar and they just launched a new line of fall casual shirts and, just like all their other shirts – they’re fantastic! They fit true to size, come in various sizes for all body types and are very high-quality relative to the price. Dorian has, over the last year or so, completely replaced his collared shirts with ones by the Tie Bar.
Both are classic go-tos for the Fall season. The darker autumn colors: dark green, darker brown, burgundy are perfect for this time of year and the thicker material makes them extra warm.
Fall is here and it’s time to give your wardrobe some consideration as the weather cools down and the season and style challenges change. Temperatures can be unpredictable and you’ve got some new occasions you’re prepping for. Don’t worry, we’ve got you! Dialing in a great Essential Fall Wardrobe doesn’t have to involve a lot of major changes, just some smart choices and a few tweaks.
So, to help you prep your closet and your wardrobe, we’re running down some of our key fall style tips with our Fall Style Do’s and Don’ts.
Fall Style Do’s
Continue To Wear Color
Just because it’s fall and its getting colder doesn’t mean you should stop wearing color. Instead of bright or pastel colors that you would typically wear in spring and summer, opt for darker jewel tones and earth tones to mix in with your neutral greys, black, and navy.
Layer Your Clothing
The temperatures in Fall can vary a lot, it’s warmer in the day and gets cold at night and it can be tough to deal with sometimes! So, proper layering is just the skill you need to master as it can help you regulate your temperature and look stylish. Start with a t-shirt or casual button-down as your base layer, then add a sweatshirt or sweater on top, and next, a bomber jacket, wool jacket, or sportcoat layered on top.
Invest In A Pair Of Boots
Boots are essential footwear for Fall/Winter and the right pair can look amazing and last a long time. Think of chukkas and casual and dress boots as your go-to base shoe for non-sneaker situations. We’ve discussed some of our favorite boots before and here are a few of our favorite picks:
It can be tempting to only wear jeans during the Fall but we encourage you to branch out to thicker chinos and wool trousers to mix up your rotation.
Flash Lots Of Bare Ankle
Obviously, if you’re in a climate where it’s still warm then this doesn’t apply to you. But if your Fall is on the cooler side, then it’s just not seasonally appropriate (or comfortable). If you want to go with a cuff on your pants try doing it with boots or heavier footwear.
Wear Lightweight Fabrics
No man should be wearing linen, lightweight chino cloth, or seersucker anything during Fall and Winter months. Put ’em away and store those until Spring. Heavier cotton, denim, wool and wool blends, and leather should be your fabrics of choice.
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.
