Fall is arguably the best season for menswear, and that includes footwear. Here are some of the best fall shoes for men to wear this year.
Decorative gourds are appearing on porches faster than you can say “grande pumpkin spice” and the trees are changing colors. Children are making hand-turkeys like their lives depend on it.
You’re starting to wake up with frosty toes, and that t-shirt you’ve been wearing all summer is developing fold lines in your drawer.
It’s fall 🍃🍂
Fall weather makes many menswear enthusiasts feel all warm and fuzzy inside (and outside). You can finally throw on layers and show off some of the heavier, more interesting pieces in your wardrobe.
But what should you wear on your feet?
We’re going to break down how to pick the right shoes for cooler autumn weather, including a list of essential shoe styles for fall.
So pour yourself a coffee, pin your kid’s hand turkey on the fridge, and start mentally checking out of work.
It’s time to put your best foot forward this fall…
What Makes a Shoe Good for Fall?
With all the layers (vests, cardigans, work shirts, jackets), fall outfits become a bit bulkier than spring and summer outfits.
Wool, flannel, corduroy, suede…these fall fabrics are thick and textured, so your shoe choices should match this bulkier profile.
You could definitely get by wearing brown boots for the entire autumn season, and we wouldn’t judge you for it.
But you can also wear sneakers, which is a great way to make your spring and summer shoes do double duty.
The point is, you have options. Here are some of our favorite fall shoes for guys to wear this year.
There are so many different types of chukka boots, from leather to suede, casual to dressy.
The brown leather chukka goes with almost anything, but grey suede is also a versatile choice.
Chukkas are a great choice because they work well with casual outfits and dressier outfits alike.
Budget Pick – Clarks Bushacre
Clarks popularized the desert boot style that was worn by British troops fighting in Northern African during World War II.
Their updated Bushacre is a casual, affordable leather chukka that’s been fan favorite for many years, and for good reason.
Value Pick – Thursday Boots Scout
A great all-around chukka is the Scout from Thursday Boots.
The Scout is a middle-of-the-road chukka, in terms of formality. It’s not as casual as a true desert boot, but it’s definitely not a dressy chukka that you’d wear with a suit and tie.
It’s perfect for casual, smart casual and even business casual looks (think chinos with a tucked in button down shirt), and the price-to-quality ratio makes it easy to recommend.
Midnight blue suede goes with many different shades of jeans and chinos, and it’s a nice addition to your wardrobe if you want to break free of brown shoes.
Dressy Pick – Ace Marks Lorenzo Chukka
If you want a dressier chukka boot that you can wear with wool trousers and suits, this Italian-made Ace Marks chukka is right up your alley.
Made from calfskin leather, this boot features “Blake flex stitch” construction, which makes it lighter and more pliable than a Goodyear welted boot.
Don’t worry, it’s still reasonable, so you’ll be able to wear this chukka for many years!
Lace-Up “Work” Boots (or Service Boots)
There are two types of leather work boots: the type you actually wear to work if you’re in construction, and the type you wear to work if you write about men’s fashion.
We’re going to focus on the latter 😉
When you start to layer vests, sweaters, and coats, your top half can get pretty bulky, so rounding out the bottom half of your outfit with a larger pair of boots will help maintain a balanced silhouette.
We love the basic leather lace-up work boot, especially if you want a minimal shoe collection.
These pair really well with henleys, flannel shirts, vests, raw denim and leather coat jackets.
Here are our top picks for this style:
Budget Pick – Eastland High Fidelity Cap Toe
For under $100, you can’t expect high-quality leather and Goodyear welt construction, but you can still get a handsome pair of boots that should last a few seasons.
These cap toe leather lace ups from Eastland are available in plenty of sizes and three versatile colors.
Temper your expectations, and you’ll probably be happy with this budget purchase.
Value Pick – Thursday Boots Captain
For under $200, you can’t really do better than the Captain from Thursday Boot Co.
These Goodyear welted boots are built for comfort and longevity. The leather is “Thursday Chrome” which is Thursday Boot Co.’s chrome-tanned leather.
They have a cork-bed midsole and DuraEVA Comfort Strip, so they should be pretty comfy right out of the box and require very little break in.
In the looks department, they’re on par with much more expensive boots like the Wolverine 1000 Mile. For more info, check out our Thursday Boots Captain review.
Splurge Pick – Grant Stone Diesel
We’re calling the Diesel from Grant Stone a work (or service) boot, but it could easily fit into the “dress work” boot category too.
In other words, you could wear them with thick wool/flannel trousers. I mean, just look at them:
The Diesel has a sleeker profile than something from Red Wing or Chippewa, so it works in a greater variety of outfits.
Although it’s made in China, Grant Stone’s flagship boot has been compared to Alden, in terms of construction quality and attention to detail.
These boots aren’t cheap, but they’ll last many, many years if you want them to!
The word moccasin dates back to the early 1600s and refers to the construction of the shoe.
These days, moccasins come in many shapes and sizes, but the look and feel is generally casual.
One great type of moccasin for fall is the blucher moc (or “ranger moc”) which is a slightly more robust version of the simple camp moc.
Although some loafers and driving shoes are constructed like moccasins, they’re not really great for fall, as they’re meant for wearing sockless (or with no show socks).
Stick with these top picks instead:
Budget Pick – Minnetonka Camp Moc
As a company, Minnetonka pretty much focuses on moccasins. Their Camp Mocs are affordable, laid back and perfect for wearing with a pair of thick wool socks.
Here’s the best part: these can totally double as boat shoe replacements during spring and summer. Just wear loafer socks or go barefoot.
Value Pick – L.L.Bean Jackman Ranger Moc
L.L.Bean has making handsewn moccasins since 1936, so they know what they’re doing.
Their Signature Jackman Ranger Mocs are almost like a great choice for boot lovers who want to try the moccasin style.
In terms of formality, they’ll wear like a desert boot or casual chukka.
Splurge Pick – Rancourt & Co.
If you’re into heritage quality goods and willing to invest in shoes that will last, look no further than Rancourt & Co.
Handmade in Maine from Horween Chromexcel leather, these are some of the highest quality moccasins you can buy.
Whether you choose the blucher style Classic Ranger or the simpler Gilman Camp Moc, you’re going to have a shoe you can wear for a long time and that will only get better with age.
These aren’t cheap, but you get what you pay for!
If you find yourself wearing white
As much as we love white sneakers, rich brown tones just seem work better in cooler months.
Gum soles look great with brown, but white soles are just fine too.
Budget Pick – Cole Haan Grand Crosscourt
While the price fluctuates a little bit, you can often find these on Amazon for around $50, which is reasonable for a leather sneaker.
Of course, you can’t expect high-quality leather or the most durable rubber outsole at this price, but these
Value Pick – Beckett Simonon Reid
Beckett Simonon makes some of the best leather sneakers under $200, and the pebbled leather Reid is no exception.
The Modest Man is a longtime fan of Beckett Simonon, and we think the texture of the pebbled leather is perfect for the autumn season.
Keep in mind, most Beckett Simonon shoes are made to order, which means you’ll have to wait a few weeks to get your hands on them.
If you want something similar, but quicker, check out the Greats Royale (wait for a 25% off sale, then grab them for around $135).
Splurge Pick – Koio Capri Mocha
These are deluxe. Heck, even if you have Common Projects money, we recommend checking out Koio instead.
These have a pretty high price tag for
The Mocha colorway is simple and stunning. Plus, minimal
Trainers are so easy to throw on for quick trips out and about, and they work with just about any casual outfit.
You can find these
Both are great for fall, especially if you pick a more colorful style.
If you’re wearing jeans or chinos, definitely feel free to cuff your pants to give your shoes center stage.
Low Profile Budget Pick – Onitsuka Tiger Mexico 66
Inspired by German Army Trainers, these classic low-profile beauties are simple and fun.
Because the Mexico 66 is available in so many different colorways (over 30 at the time of writing), you can really tailor them to your wardrobe.
If you really want to match those fall vibes, go with something like tan/brown or burgundy/white.
Or stick with the classic red/white/blue for an easy four seasons style.
Chunky Budget Pick – New Balance 574 V2
New Balance’s updated take on their classic 574 silhouette is a great choice for fall.
These won’t break the bank, and they’re available in a lot of different color combinations.
Granted, some of these colors wouldn’t be our first choice. But some are surprisingly cool and perfect for fall.
If you’re not into New Balance as a brand but like the idea of a chunky, colorful sneaker, check out the Saucony Shadow.
Value Pick – Nike Killshot v2
This is truly a legendary four season sneaker, but the Killshot 2 has certain features that make it great for fall, like the gum sole and suede accents.
The “Desert Orange” colorway is especially autumn-y. Then again, these sell out quickly, so it may not be available by the time you’re reading this :/
Splurge Pick – Koio Retro Runner
The Koio Retro Runner are decidedly chunky which puts them on the forward end of fashion.
But we think Koio’s interpretation of the “ugly shoe” trend is spot on.
These aren’t for everyone, but if you don’t hate them, you might just love them.
Chelsea boots are one of the most versatile types of boots you can buy, and they’re perfect for fall and winter.
A great pair of Chelseas will work with everything from raw denim to flannel trousers.
They look fantastic dressed up and dressed down, so investing some money in a good pair will pay off.
Budget Pick – New Republic
Although not cheap at over $100, these are very much a poor man’s Common Projects.
For the price, it’s hard to find better quality and style, which is why these New Republic boots are often touted as the best affordable Chelseas.
If you’re interested, you can read our brand review of New Republic here.
Comfy Pick – Amberjack Chelsea
Amberjack specializes in comfortable men’s dress shoes and boots.
They try to make shoes and boots that feel more like running shoes, and after personally test driving their Chelsea boot, I can confirm that it is incredibly comfortable.
Unlike other Chelseas, these boots lack a pull tab on the heel. I like this, as my pants are always getting stuck on the pull tab.
Value Pick – Thursday Boots Duke
Thursday Boots does a great job in general, but their Duke Chelsea boots are outstanding.
I mean, a Goodyear welt Chelsea for under $200? Incredible!
They go exceedingly well with denim, but this silhouette works equally well with cotton chinos or thicker wool pants.
Keep in mind, the Duke is a more casual Chelsea boot, so they will look out of place if you try to dress them up too much.
For a slightly more refined boot, check out the Beckett Simonon Bolton.
Splurge Pick – Common Projects
If you want amazing quality and design, and you’re okay with paying the extra markup for one of the coolest designer labels, Common Projects is the way to go.
These are some of the sleekest, most refined and minimal Chelsea boots you can buy.
We especially like the taupe color, which will look great with literally any shade of denim in your closet.
Unless humans take up space travel and space boots become the new normal, bluchers will never, ever go out of style.
Suede bluchers are a great shoe for everyday wear, especially if you work in a business casual environment.
This somewhat casual lace-up style suits a smart-casual and business casual wardrobe, and suede bluchers can be worn all year round.
But the texture of suede really compliments cold-weather fabrics like wool, cashmere and corduroy.
Budget Pick – Eastland Buck Oxford
Eastland has been around for a long time, and they make a solid shoe for the price.
The Buck isn’t the best blucher ever made, but it’s a relatively low-cost way to add this versatile style to your arsenal.
Plus, the brick-red rubber outsole fits right in with a summer or winter wardrobe.
Value Pick – Beckett Simonon Dunham Derby
Direct to consumer brand, Beckett Simonon, gives you a lot of bang for your buck (or derby, in this case).
If you’re okay with made-to-order shipping times – think ~2 months – the Dunham Derby is an excellent suede lace up for your smart shoe collection.
Either color – chestnut or brown – will look good with pretty much any non-black pants you own.
Splurge Pick – Grant Stone Longwing
The Longwing from Grant Stone is an elevated wingtip blucher with broguing along the upper.
We liked the extra decoration, and our experiences with Grant Stone have always been good.
This is a high-end shoe on par with brands like Allen Edmonds and even Alden. It will last many, many years!
Dress boots go way beyond fall. They’re style staples in their own right.
But they do make sense for colder weather since they offer a bit more protection and warmth than dress shoes.
Budget Pick – Rockport Colden Wingtip
A couple of disclaimers here…
First, Rockport is best known for comfort, not style. Second, you can only expect so much from a dress boot under $100.
You’re not going to get high-quality leather, Goodyear-welt construction or a boot that lasts many years.
But these Colden Wingtip Boots look pretty darn good for the price, and they’ll have that comfy, broken-in feel that people expect from Rockport.
Value Pick – Beckett Simonon Elliot
We’ve been longtime fans of Beckett Simonon. Their styles are timeless but not stuffy, and the brand offers incredible value for the price.
Their Elliot Balmoral Boots are some of the coolest dress boots under $250 on the market.
They’re sleek and sturdy, and they’ll look great under wool trousers, jeans or any type of chino.
The Oxford style construction and leather outsoles make these look like a formal dress shoe from the ankle down, so feel free to wear them with a suit.
Splurge Pick – Allen Edmonds Dalton
Bust out these legendary wingtips when you want to impress. They’re not cheap, but if you want a sophisticated, well-built dress boot, Allen Edmonds has you covered.
These wingtip boots are one of Allen Edmonds’ bestsellers, and for good reason.
They just check all the right boxes, especially if you prefer the sturdy, heavy build that the iconic American shoemaker is known for.
Loafers? For fall?!
I know, I know…but loafers are actually way more versatile than most guys think they are.
You wouldn’t want to be caught in really cold, snowy weather with them. But put on a thick pair of socks, and you’ve got some great treads for fall.
If you’ve only ever worn your loafers during spring and summer, try them out with some wool socks this fall. You might be surprised how comfy and stylish loafers can be as the weather cools down!
Budget Pick – G.H. Bass Weejuns
It’s said that the Weejun made loafers popular in the States. We’re not sure if that’s true, but these classic penny-loafers have definitely aged well.
In terms of formality, these your classic middle-of-the-road penny loafers.
They’re perfect for casual, smart casual and business casual outfits, but they’re not formal enough to wear with suits.
Value Pick – Jay Butler Millbank Bit Loafer
Bit loafers have a little something extra than their plain penny loafer cousins, so they’re perfect for guys who want to stand out from the crowd.
Jay Butler specializes in loafers, and their Millbank bit loafer is probably the best horsebit loafer under $200.
The olive and burgundy colorways are perfect for fall, and the suede makes these the ideal footwear for kicking back by the fireplace.
Splurge Pick – M.Gemi Sacca
For a premium suede loafer, look no further than the Italian direct-to-consumer brand, M.Gemi.
Specifically, their best-selling Sacca loafer is our top pick.
The soft suede texture is perfect for fall, especially when paired with thick cotton or wool socks.
These are no-go’s for snowy winters, but come spring and summer, you can go sockless as the Italians do.
For more details about these loafers, check out our M.Gemi review.
High tops are like
They’re not quite as versatile as low top
Still, if you live somewhere that keeps you wearing pants for most of the year, you’ll get plenty of wear out of your leather high tops.
Budget Pick – Cole Haan Grand Crosscourt
It’s hard to find any decent quality leather high tops under $100, but these Cole Haan Crosscourts are pretty darn good for the price, especially if you can snag a pair for as little as $75.
They’re available in all of the basic, neutral colors that most guys gravitate towards. We especially like the lighter brown colorway for fall.
Value Pick – Greats Royale High
If you can spend a little more, wait for these Greats Royale high tops to go on sale for 25% off, and grab them for around $150.
Made in Italy with premium materials like full-grain leather and waxed cotton laces, these are very comfortable right out of the box and an incredible value for less than $200.
Splurge Pick – Koio Primo
If you want the very best, we got you covered. Check out the Koio Primo high top.
Hand-crafted in Italy from premium materials, these are luxury
Everything from the clean silhouette to hand-painted edges is premium. If you have the budget for them, you won’t be disappointed with the Primos.
Question About Men’s Fall Shoes
Here are answers to some commonly asked questions about fall shoes for guys:
What shoes can you wear with jeans during fall?
The best shoes to wear with jeans during fall are boots, brown
What shoes do you wear with skinny jeans?
You can wear any type of shoes with skinny jeans, but keep in mind: the slim leg opening may not fit over the collar of a boot. For that reason,
What shoes do you wear with straight leg jeans?
You can wear any type of shoes with straight leg jeans, including chunky
Can you wear
sneakers in the fall?
Yes, you can wear
When it comes to finding the best shoes for fall, you’ve got plenty of options, and most of these styles can be worn all year round (which is great if you’re building a minimalist shoe collection).
What’s your favorite pair of shoes or boots to wear during the autumn season?
Let us know by leaving a comment below!
I really like your reviews. May I suggest putting comfort ratings in your reviews? Style is one thing but I am more in to shoes that do not have a hard inside bottom and are comfortable to wear. Nothing worse than buying a $200 pair of shoes that hurt your feet or worse-gives you blisters. I find this the case with many dress shoes. They have very little grip when walking, they hurt your feet and put a big blister on the back of your foot even with thick socks. Also, possibly a grip when walking rating? All important stuff when considering buying shoes wouldn’t you agree?
Left this post last year 08/2020, you didn’t respond so I’ll try again.
I have a couple pair of hightops that are actually considered boots one pair black with white soles by Garcia from Beckett Simonon and a pair of tan, similar to what’s shown, with white soles from Asos for only $79. My brown suede loafers also come from Beckett Simonon Roy Penny Loafer https://www.beckettsimonon.com/products/roy-loafers-suede?variant=29612756402255.
What do you think about suede double monks by Stacy Adam’s for fall? I have a 2 pair in tan and light sky blue. I’d post a pic but can’t here.
My suede Chelsea boots are inexpensive by Merona (from Target). I also have brown suede wingtip by Claiborne. I noticed you didn’t mention those.
What are your thoughts on shine? Many of your selection have high shine. When I wear high shine boots/shoes to buy groceries in my rural west of 5k population–it’s seems a little too pompous? I’d imagine a city setting or a night on the town would fit high-shine perfectly, but I’m literally surrounded by men with work boots on–about to go cut some log pole pine trees down. 😉
I don’t mind a little sheen, but it usually wears off as your shoes develop a patina. If you don’t like any shine, I’d go with rough out or pull up leather, or suede.
Tim Goldsbury says
Just a comment on shoes. Ye, I have followed you site for some time. Pardon me, but as a short guy, I think you are missing it.
Flat heels don’t cut it.
In the UK they make some fantastic dress shoes with actual heels. These often help avoid a fall and slightly improve one’s stature.
It’s hard to find these quuality shoes at a reasonable price, and the shoe industry today is in to the the flat heel design for men.
It takes research to find the shoes described. Years ago they were common. Check the dress shoes with heels that many performers where on camera.
Thanks, Tim Goldsbury
To each his own, but I personally don’t prioritize height boost when choosing shoes. That said, most work/service boots have at least a 1″ heel, if not more. Some mocs (like Yuketen Maine Guide shoes) have about 2″.
Anything more than that makes it hard to walk, in my opinion.
But of course, wear whatever you like! Thanks for commenting!
John Almodovar says
Need 6” in black for work and play
Ryan Anderson says
Can anyone tell me the brand and model name of the trainers the model is wearing in the first photo under “Brown Minimal Sneakers”? The ones with the gum soles and gold laces. Those are killer!
Those are from Ace Marks. Tbh they haven’t held up as well as some other sneaker brands I’ve tried.
All great selections. I have 1 of every pair except the the dress work boot because my casual work boots (a pair of black and brown) by San-Polos Valentino also serve as dessert boots. I have a couple pair of hightops that are actually considered boots one pair black by Garcia from Beckett Simonon and a pair of tan with white soles from Asos for only $79. My suede loafers also come from Beckett Simonon brown Roy Penny Loafer https://www.beckettsimonon.com/products/roy-loafers-suede?variant=29612756402255
What do you think abot suede double monks by Stacy Adam’s for fall? I have a pair in tan and light sky blue. I’d post a pic but can’t here.
Another excellent, well researched and highly informative article, Brock
You are presenting these different type of shoes in a great way
After reading this article I am ready to buy some shoes, right now