Men’s Fall Fashion 2020: 25 Style Essentials

Once the summer is over and Fall begins it’s a good time to invest in some new hiking boots. Most folks think that the summertime is the best time to go for hikes, but if you live in the Northeast like I do the Fall is a great time to hike and do some leaf-peeping. If you are planning on investing in a great pair of new boots, Timberland is one of the best choices you could make. They make a ton of great clothing but are known for their boots.

This pair of boots is not only fashionable but specifically designed for hiking and keeping your feet comfortable while doing so. You could hike thousands of feet in these boots and not have to worry about getting wet or cold or too hot. These boots fit snug and will allow you to stomp around in mud, puddles, and through the brush, if you want to go off-trail. The boots come in a ton of sizes and are also available in 5 different colors. 

While you can wear a hoodie year-round, Fall marks the unofficial start of Hoodie Season. If you live in a part of the world that gets four seasons of weather then you know how great the hoodie season actually is. Warm enough to not wear a coat or jacket but cool enough that you don’t sweat bullets all day long. Hoodie season is definitely my favorite time of year and for those of you that wait for the Fall to get your hoodie collection in full rotation, you are going to love this hoodie.

Carhartt is well known for making clothing that is not only comfortable and stylish but incredibly durable as well. This hoodie is a 50/50 cotton and polyester blend so it is super comfortable and can take a beating. If you are in need of a clutch work hoodie or something to wear while hiking around the woods or up your favorite mountain than look no further. Get yourself a Carhartt hoodie, which comes in regular and Big & Tall sizes and is also available in 17 different colors so you can buy a couple and really boost your hoodie collection.

You can definitely wear jogger pants all year round, but you may find them a little too thick for summertime and a little too light for the winter, depending on where you live. They really are the perfect pant for Fall. If you are typically a regular sweatpant guy you should consider trying out joggers. They have a sweatpant feel but look more like regular pants. They have become more and more popular over the past few years after being seen on rappers and actors and athletes. 

These South Pole joggers are light enough that they won’t make you too hot but are heavy enough to keep you warm on chillier days. You’ll love the way they fit and the way they look with your outfit. You can rock a tee shirt and sneakers with your joggers or a hoodie and boots. These joggers are available in a ton of different sizes including Big & Tall sizes and they also come in 9 different colors. They are available in some earthier tones which are perfect for the Fall season.

The weather definitely changes gears during the Fall months and you want to be ready for anything. Under Armour has a great track record for athletic gear but their jackets are also pretty stellar. I have an Under Armour windbreaker jacket similar to this one and it not only fits great but definitely keeps me dry no matter how hard the rain is coming down. 

If you like to spend time outdoors during the Fall season then getting a jacket that is durable and comfortable is a good move. This jacket will keep you dry on the rainiest days and will keep you warm when the temp starts to drop. If it gets a little warmer outside than you anticipated this jacket won’t overheat you. It’s available in a bunch of sizes and comes in some great colors so you can go bright or dark and either way, you are going to look your best. This is a great jacket to have in your arsenal.

Beanie hats are a great mix of style and function. They have become crazy fashionable in the past couple of decades and taking a look at this cool beanie from The North Face you can see why they are so popular. The beanie is a low maintenance hat that you can keep in your back pocket when you aren’t wearing it and just toss it on if the mood strikes you. The beanie keeps you warm without overheating your head and that is perfect for Fall weather.

The North Face is known for their winter wear but don’t sleep on their beanies. This beanie will go great with whatever you wear and is lightweight enough that if the weather is warmer than you expected you won’t sweat through it. The soft fabric makes this hat super comfy and if you are a beanie fan like I am you are going to want to get a couple so you have some color options. This beanie is available in 9 different colors so you can mix and match with different outfits and be the most fashionable guy in your crew.

Regardless of whether you are a world-class angler or just a Sunday fisherman, this is a pretty dope hat and one that you will love to wear while you are out on the water. Just because you aren’t getting any bites doesn’t mean you can’t look like a pro. This Columbia hat is a great addition to any guy’s wardrobe. While Fall is a great time of year to get some quality casts in you can wear this hat year-round. 

This hat features the American Flag and the stripes are actually fish. It comes in a bunch of great colors but the featured is probably the coolest. The red, white, and blue look is a look that is perfect for Fall. While most people will tell you that you shouldn’t stray from the earth tones in the Fall months you can also wear bright colors especially if you are spending a lot of time outdoors. Check this hat out in some of the other colors that it is available in. There are 18 total colors to choose from.

Fall is a great time to rock some new khakis. Afterall, khakis are traditionally earth-toned and can be worn either to work or after hours. If you are an outdoorsy guy that likes to spend time in the mountains or on the lake then these durable khakis from Dickies are a great choice. They will pair perfectly with a shirt and tie at the office and with a flannel and some boots on the weekend.

Dickies has a reputation for making work pants that are nearly indestructible. These pants are made to last and if you aren’t the kind of guy that likes to invest in a new pair of pants every 6 months then these are a great choice. You can wear them fishing, hiking, hunting or just hanging with friends. They are easy to pair and if you don’t like the traditional khaki color, no worries, they are available in 17 colors so you can buy a few pairs to fill out your dresser drawers. 

Denim is going to be huge in men’s fashion this Fall. this Levi’s Sherpa Trucker Jacket is a great addition to your Fall wardrobe as it is fashionable, comfortable, and is easy to pair with the rest of your clothes. In fact, this jacket isn’t too heavy on the denim that you couldn’t wear jeans with it. It is a great pairing with a darker pair of jeans, sneakers or boots, and a nice button-down or tee shirt underneath.

While the jacket has a bit of sheepskin on the collar and on the interior it won’t be too hot on those warmer Fall days. You can wear this jacket to work or to play. It is a great first date jacket or 20th-anniversary jacket. If you aren’t really feeling it in the featured light blue I have some good news for you. There are 8 other colors that you can choose from that will fit your own personal style. Make sure you pick a color that will pair with the rest of your wardrobe and it might be a good move to get one dark and one lighter colored denim jacket so you have all your bases covered. 

If the Fall chill doesn’t push you to pull out your bigger thicker jackets then you will need something to help keep that cold air off of your neck. A brand new scarf will help protect you from the cold and can add a little something extra to your wardrobe. The right color and texture will help bring out the other parts of your ensemble while also allowing you to walk around in a light jacket or hoodie. Luckily scarves tend to pair with most formal and semi-formal outfits and can also be worn in a casual look pretty easily. 

This scarf has a thick body to keep your neck and chest warm and the fringes will add depth to your look. The scarf is made with 100% cashmere so it is incredibly soft. You are going to love the way this scarf looks and feels on your skin. The solid colors of the scarf are a great way to pair your clothing. Wearing a shirt or pair of pants that matches the scarf will complete your outfit nicely. There are multiple colors to choose from. The scarf measures 12 inches wide and approximately 72 inches long. 

Flannel shirts are a great pick for Fall fashion. They are comfortable, not too warm, not too cool and they look great. You can pair them with khakis, jeans, work pants, or even sweats if you plan it right. Fall is the perfect season to show off your style and if you are a fan of colors then a flannel shirt is a smooth move. Legendary Whitetails is known for its comfortable and durable flannels and this shirt will keep you nice and cozy around a campfire or at the job site.

The shirt is made from 100% cotton so it is comfortable and soft against your skin. You can wear the flannel untucked or tucked in but if you do tuck it in make sure you wear a belt for a more complete and polished look. Pair this shirt with your work clothes or outdoorsy gear. This shirt is available in a ton of great colors and comes in sizes ranging from regular to Big & Tall so there is something for every sized guy. Fill your closet with a bunch of new flannels and you’ll look great all Fall long. 

With the changing temperatures during the Fall season, you are going to want a bit of durability from a hoodie. A zip-up hoodie will allow you to take the hoodie off when the temp rises and put it back on when the sun goes down and it gets a bit chillier. Also, zip-up hoodies look great underneath a jacket so you can layer and show off how fashionable you really are with a dope hoodie like this and a solid jacket. The red is a clutch color and is incredibly popular and trendy especially in the Fall months. 

Nike is a great choice on a hoodie because it is made to last. The hoodie can be worn playing basketball or working out, it can be worn over your work clothes and obviously can be worn casually on a camping or hiking trip. The hoodie has a fleece liner so it will definitely keep you warm when it gets cold outside so while you are buying it for a Fall fashion, you can still wear it year-round. IF you aren’t a big fan of the red of the featured hoodie there are 5 other great colors to choose from. 

I once had a pair of New Balance running shoes that I never really ran in that lasted me almost 10 years, and I wore them 3-4 times per week. New Balance got their start as a running shoe manufacturer and they took that technology and put it into every pair of kicks that they make. These casual shoes can be used on the track but are more for just kicking it. They are comfortable, come in bright colors, and are a perfect pairing with a ton of different outfits. 

If you have a pair of jeans, khakis, shorts, or sweatpants then you have a pair of pants that will look great with these kicks. The featured pair are super fun and will definitely stand out. You will get complimented on these shoes almost any time you wear them. The mix of suede and textile help to keep these sneakers looking fresh for years. If you aren’t completely sold on the featured colors then check them out in some of the other colors that they come in, there are 24 total colors to choose from. 

Leather is going to be huge in men’s fashion this Fall season. Leather is always a good choice, weather permitting, but this fall the leather jacket is going to trend big time. Picking the right leather jacket can be a painstaking feat. You want something that is going to last for years but will be fashionable for all of those years. The way fashion changes it can be tough to pick a look that will stand the test of time, luckily leather always seems to look really good.

Flavor makes one hell of a nice looking leather jacket. This jacket is the kind of jacket you can wear over a hoodie or with a more formal outfit. The bomber look has always been a cool style and if you take care of this jacket the way that you should a leather jacket, it will last you a long time. The pigskin leather is a softer leather but more durable than other hides. It has a distressed look that won’t have to be broken in for years to obtain. If you don’t like the featured brown, there are two other colors including black that this jacket is available in. 

Even though the weather turns a bit colder in the Fall months there are still those guys that refuse to wear pants. They are the bravest of the brave, wearing shorts year-round is a bold choice, but can be a good one with the right pair of shorts. Dockers make a quality product. From pants to shorts to shirts they are world-renowned for their fit, finish, and comfort. So it makes sense that they would make a pair of shorts called the “Perfect Short”.

Lightweight and comfortable these shorts will pair well with nearly anything, as long as you wear the outfit correctly. When you tuck your shirt in you should always wear a belt, it just looks cleaner, like you paid attention and care about how you look. You can wear a hoodie or just a plain tee with these shorts and look great. Play a round of golf in them by day and hit up your favorite watering hole by night. They come in a bunch of sizes for any sized guy and are available in 10 different colors so you can stock up and have a bunch of different looks to try out. 

Slippers or house shoes are one of those pairs of shoes that can be worn year-round, but there is something about the Fall that just screams comfort. The great thing about slippers that have rubber soles is that you can wear them indoors or outdoors and any time of year. UGG is well-known for making one of the most comfortable shoes on the planet. The soft interior and durable exterior make for one hell of a pair of slippers. 

Sliding into these slippers every day is going to be a welcomed treat. You can lounge around the house and not worry for one second about your feet or you can slip these bad boys on and go to the store, hit up your local restaurant, or even go on a first date. They are fashionable, stylish, and pair well with anything. Slide them on and put a pair of jeans over them and you will look and feel fantastic. If black doesn’t pique your interest there are three other colors to choose from and they are all spectacular. 

Staying true to the fact that denim is always a good choice any well-dressed man has at least one pair of trusted and tested jeans in his arsenal. Wrangler is a brand name that you cannot go wrong with if you are looking for jeans. Wrangler denim is tough, rugged, comfortable, and doesn’t take weeks of wear to be broken in. These jeans have a bit of a retro vibe to them which means you can wear them with almost anything. They are slightly worn and distressed so they look and feel broken in right when you slide them on for the first time.

The right pair of jeans will only make the rest of your outfit look better. Your shoes will pop, your shirt or hoodie will stand out more and your jacket, if you are wearing one, will help compliment the rest of your body. These jeans are a great investment and barring some unforeseen accident they should last you for years and years. I always recommend buying multiple pairs if you find something you like. Check out the different colors that these jeans come in and give your denim drawer a boost. 

Things can change pretty drastically from the summer heat to the chill of autumn so it helps to be prepared for the drop in temperature. Some guys have a bit of trouble making the jump from short sleeves to long sleeves so it helps to have some clothing that will bridge the gap. Having a comfy vet in your closet is a great secret weapon to have ready for when you don’t feel like wearing a jacket but it is a bit too chilly for just a tee. This vest is as stylish as it is cozy and makes for a great centerpiece to the perfect outfit.

You can wear almost anything with this vest. Dress it down with a casual look, just throw on some jeans and sneakers with a tee underneath. IF you are looking for a more formal look you can wear a button-down or flannel under this vest with some khakis or work pants. Columbia makes some seriously great clothing that comes in regular as well as Big & Tall sizes so there should be something for every size guy. There are 25 different colors in this style vest so you should be able to find something that works with your existing wardrobe. 

Thermal shirts are a hot look during the Fall and Winter months. The stitching makes them surprisingly warm even with a minimal thread count so they are great for when warmer weather turns cold. Mix the warmth and comfort of a thermal or waffle shirt with the durability and style of a Burton hoodie and you have yourself a men’s fashion home run. This is one dope hoodie that is going to be perfect no matter what you are doing and who you are doing it with.

The cotton and polyester mix makes this hoodie lightweight but also very warm when it gets cold out. The stitching adds a bit of depth and dimension to the look. You can wear this hoodie with a pair of jeans or a pair of snow pants, either way, you are going to turn heads. You can wear this hoodie with almost anything in your wardrobe, year-round and you are going to be fashionable as hell. IT comes in the featured color as well as two other colors that really make the texture of this piece pop!

Most guys typically don’t wear long underwear under their clothes until winter hits, but once the fall chill starts to roll in I like to break out the long underwear for sleeping. Long underwear, long Johns, or thermal underwear are super comfortable to the point where you forget that you are wearing them underneath your clothes. They hug your skin and are super soft and are the perfect thing to sleep in when it gets colder during those chilly autumn nights.

If you are going to invest in long underwear you want something that won’t itch or scratch your skin. Wearing something that close to your skin and having it be irritating is the worst feeling. The long underwear in this list is super comfy though so no worries there. While being warm they are also incredibly lightweight which makes them perfect for winter wear or fall sleeping. While color won’t really matter when you’re wearing these under your clothes there are six great colors to choose from. 

For the man that needs a new pair of boots to work in, I highly recommend the Wolverine work boot. I own a pair of Wolverines and they are without a doubt the best work boots I personally have ever owned. They are durable, they are comfortable and if you are a guy that wants to add a couple of extra inches to your height, they will do that too. They are slip-resistant which is a great feature if you have ever taken a digger and fallen to the floor or pavement before.

These boots come in standard sizes and wide sizes for guys with a wider foot or higher arch. No matter how hard you beat on thee boots during your day to day they will feel and act as if they are basically new. They don’t take a long time to break in and once they do they feel like heaven on your feet. The greatest thing about these boots is that you can wear them to work in or you can wear them just walking around. You can hike in them, you can fish or hunt in them, they are a true every man boot. They are available in two great colors that won’t fade or deteriorate over time. 

As the sun starts to go down and the wind starts to pick up you are going to need a jacket that you can wear to work or wear in your outdoor pursuits. This Carhartt jacket is the perfect jacket to accompany you on your camping trips. It’s the jacket you will take with you hunting and fishing and the jacket you will pull on when the weather report calls for rain or even snow. The flannel lined jacket will definitely keep you warm when it needs to but won’t make you sweat when the weather isn’t terrible.

Made from 100% cotton this is a great jacket to fight the elements. You are going to have this jacket with you no matter what. Stash it in your vehicle for when the cold comes out of nowhere and if it starts to rain or snow, this jacket will protect you without getting heavy or waterlogged. It comes complete with deep pockets and a thick hood to protect you from head to waist. It is available in a ton of sies so every guy can find the right fit and is also available in multiple colors so you can match your style perfectly. 

I am a firm believer that you can never have too many pairs of comfortable sweatpants. With the men’s fashion world becoming more and more casual jogger sweatpants have become more and more popular. These sweats are designed by jeans juggernaut True Religion. If there is one thing that the True Religion brand knows it is how to make a great pair of pants. Twenty years ago, guys didn’t view sweats as an item that could really show off their unique and individual style. Nowadays sweats are super stylish and pairing style with comfort is a rare treat. 

The 100% soft cotton makeup of these pants will keep you warm but not too hot. They are supremely comfortable and you are going to find yourself looking for reasons to wear them. Kick back at home and watch the game in these sweats or go out with friends and enjoy the last bit of warm weather while wearing them. I recommend buying multiple pairs of these amazing pants so you can stay comfy all week long. There are six different colors and sizes ranging from small to 3XL.

No matter the season a great timepiece can really set off a man’s outfit. The shine of the stainless steel can tie together a shirt and pants combo. Pairing a watch with shoes or a pair of shades is a great move and not enough men know how to accessorize correctly. This chronograph watch from Fossil, a giant in the watch and sunglass game, is a beautifully designed timepiece that can be worn casually or with your shirt and tie when you go to work for the day.

This is a lightweight watch that will go well with any of your outfits. You can wear it on a trek through the woods while hiking or fishing or while heading up a big business meeting. The red face is the perfect color for Fall and one of the most popular looks of the upcoming season. If you aren’t sure if the red face is right for you then you can pick one of the other looks, there are plenty to choose from. You can also choose from a leather band which is a more classic relaxed look or the steel band which you see featured in the featured picture. There are a total of 13 different styles to choose from. 

Working out when the weather gets to be a bit chillier can be a tough task. Warming up, stretching, and getting loose takes a bit longer and you are more susceptible to injury because your body isn’t ready to perform. Investing in a heatgear shirt from Under Armour is a great way to prevent the cold weather from cutting your workout short. The tight-fitting shirt is designed to trap your bodies natural heat and keep it from escaping. The shirt is comfortable and is the perfect article of clothing to wear while working out in the colder weather. 

If you have ever owned an Under Armour product then you know how amazing this technology is. The brand was one of the first manufacturers of this kind of material and the mix of polyester and elastane is not only designed to keep you warm but designed to fit your body like a glove. Athletes on the professional and college level trust in the Under Armour brand to keep them in the game longer. You can get the shirt in a ton of different sizes and it also comes in 16 different colors to match what your team wears.

This hoodie is the perfect mix of casual and fun to wear this coming Fall. The flannel exterior combined with the hood makes for a really awesome piece of clothing. While this hoodie isn’t form-fitting it is a little tighter than your typical baggy hooded sweatshirt. The pattern on the exterior of this hooded sweatshirt just screams Fall fashion and is a great item to sport with either a pair of khakis or a pair of jeans and your choice of shoes. you can rock boots, sneakers or dress shoes with this look.

While you probably shouldn’t wear this sweatshirt to the office you can wear it in a business casual setting or maybe even on a Casual Friday. The pattern is perfect for fishing, hunting, camping, or any other outdoor activities. Once you throw this hoodie on you aren’t going to want to take it off. It comes in a number of sizes for smaller guys to bigger guys so no worries if you don’t wear an average size, H2H has you covered. You can also buy this hooded sweatshirt in 24 different colors and it also comes in short and long sleeve styles.