As someone who grew up in autumnless LA and spent my college years in autumn-heavy New England, I’m a big fan of fall.
It’s football season, people.
However, one thing I never liked about it is having to switch up my starting line-up of shoes. See, if it went straight from summer to winter, that would be easy—sandals and light canvas sneakers to the back of the line, protective boots to the front.
So if you’re like me, well what I used to be like, you rack your brain over what shoe styles from the summer stay and what go, and what new styles to put in heavy rotation.
The round-up of the best fall shoes here will make it obvious and easy for you.
Table of Contents
3 Things to Consider When Picking a Shoe for Fall Style
1. Material and Construction
It’ll be a lot cooler in the fall with a lot more weather variation, so you want to keep the light canvas and open-toed (or open-backed) resort pieces in storage.
Sure, there are those unseasonably warm days in early autumn, but a simple GAT or leather sneaker will be more comprehensive than, say, a light plimsoll. Think about it, even if it’s a warmer day, you may end up trudging through wet leaves.
Of course, you’ll be wearing more leather than you did in the summer.
2. Color
We’ll get into specifics when it comes to leather colors later, but you’ll be switching from light, breezy shades to earth tones and muted warm colors.
Brown, burgundy, and olive are great options. Orange and yellow carry on from the summer, but go for burnt orange and mustard instead of the livelier hues.
For the most part, you want to avoid extremes. So instead of, say, black shoes, go for charcoal. You can wear white leather sneakers, but it would definitely be more fall-appropriate if it had, say, warm accents on them.
3. Occasion and Dress Code
This should go without saying, but always consider the dress code. In summer, formal occasions or semi-formal occasions like weddings and cocktails often happen outside or on the beach.
So while wearing a blazer with canvas slip-ons may have been appropriate at a summer networking event on a patio, suede loafers are preferable during a fall networking event in a boardroom.
7 Best Fall Shoes for Men
Best Sneaker for Fall: Beckett Simonon Reid
Every fall wardrobe absolutely needs a low-profile minimalist sneaker. After all, they look just as good with cuffed chinos as they do with tweed. What’s great about the Reid from Beckett Simonon is that, yes, you can go for the classic white colorway which is more or less a year-rounder.
However, they also have an all-black, which can take you into winter, and a bordeaux and a navy accented variant (among others) to go with your autumn browns and cool reds.
I’ve raved about the Reid sneaker on several occasions, but let me remind you that Beckett Simonon cuts the middle-men and uses a made-to-order small-batch model. This is why you get designer-shoe level quality for what seems like a weirdly low price.
Some notable specs include its full-grain calf leather construction, which by the way is gold-rated for eco-consciousness by the Leather Working Group. On top of that, there’s a high level of hand craftsmanship here—I’m talking hand-made shoes, strategically hand waxed to up the shoe’s resistance, and looks of course.
Beckett Simonon was founded by leather pros after all, so leave it to them to find all of the tricks of the trade.
What I Like
- Made from calfskin leather, the Reid flaunts an extremely smooth and supple upper thanks to the hide’s natural fine grain and durable pliancy.
- Though the main colorways are versatile black and white, there are some fun accented options that work beautifully for fall outfits.
- Thanks to Beckett Simonon’s expertise in leather and their clever business model, this shoe (like all of their models) are handmade by artisans offering a high level of quality assurance.
What I Don’t Like
- As clever as their business model is, Beckett Simonon shoes will definitely take a long time to ship because of it. When I wasn’t sure whether or not I wanted the all-white or (and?) the bordeaux, I just bought both at once. It’s easier to return one pair if I end up not liking it, rather than waiting another few months if I later decide to pull the trigger on another colorway.
What Do Other Reviewers Say?
Beckett Simonon shoes get loads of love for their quality for price. Sure, there are complaints about the wait time, but most of us coming into this understand we pay with our time rather than our money given the below-market price points.
Several reviews praise the brand for their attention to detail, which I fully agree with. Some examples include a supportive yet soft padding on the collar, and the tall instep which provides comfort and security.
The Verdict
At this well-below-200 price point, you’d be hard-pressed to find a minimal sneaker that’s as equally as high-quality as the Beckett Simonon Reid.
The calfskin leather is lush and strong, the fit is comfortable, and the craftsmanship is truly impeccable. Depending on which variant you go for, a lot of their colorways can take you from fall to winter, while others are easy year-rounders.
While it may take you around three months to get your feet into these bad boys, they're well worth the wait. Made-to-order, crafted from full-grain Italian leather with a Vachetta leather lining, the Reid packs a ton of value at this price point. We also love that the eyelets are hidden to make for a slightly sleeker look overall.
Most Versatile Boot for Fall: Thursday Captain
Like trench coats, the leather service boot has roots in pragmatism and was developed for the army. This is how you know it’s a menswear essential. The Captain from Thursday Boots is a legit specimen of the category, boasting a robust and tough build, but a slick and stylish look.
By the way, this very combination is the philosophy Thursday was founded on: Filling the market gap between good-looking but impractical fashion pieces and real-deal work boots that lacked sleekness. This boot was one of their very first models.
Every single variant of the Captain is perfect for fall. You can go for ruggedly handsome suede versions, beautifully oiled smooth leather, lugged soles to stomp across the piles of wet leaves October tends to bring—heck, even the green olive variant and blue marino are cool and forest-hued enough for autumn.
And since this is Thursday, this hard-wearing shoe is made of resilient full-grain leather, and is even Goodyear welted. Even more, the steel shank and comfort system (which includes a glove leather interior and shock-absorbing insoles), efficiently balances stability and comfort.
What I Like
- For less than $200, this full-grain leather boot is impressively Goodyear-welted, ensuring a long life and the ability to be resoled.
- Once broken in, the shock-absorbing, antimicrobial insoles, fully lined leather interior, and foot-conforming cork midsoles provide comfort even on long walks.
- With sizes starting at a men’s 6 all the way up to a 16, with medium and triple wide options available, the range offered is both unique and considerate.
What I Don’t Like
- The heel is a bit stiff before break-in.
What Do Other Reviewers Say?
Reviewers rave over the combination of good looks and topnotch build. No surprise there, this is Thursday after all.
There are some reviews that mention that the boot runs large. I’m not blaming them since I’m not especially detail-oriented myself, but Thursday does clearly instruct ordering half a size smaller on the website.
The Verdict
With its practical construction yet classically attractive aesthetic, the Thursday Captain is an effective boot on all fronts.
The tough leather and Goodyear-welting make it strong and long-lasting, while the combination of a steel shank with several comfort features serve up security with comfort.
The men’s service boot is definitely quintessential to a fall wardrobe, and the Captain is a truly comprehensive example.
Our pick of the best value service boots under $200, the Thursday Captains are made with supple, well-oiled leather and combine comfort with strength and stability. In addition to its Goodyear-welted construction and embedded steel shank, the cork midsoles will conform to your feet while the insoles are shock-absorbant.
Best Dress Shoe for Fall: Allen Edmonds Fifth Avenue
The Allen Edmonds Fifth Avenue is my absolute favorite Oxford shoe, and that’s because it achieves a tough balance of being both specific yet completely classic.
Of course, the fact that Allen Edmonds is one of few surviving American heritage brands that have kept up their high standards in the face of steep competition plays a big part in this shoe’s overall esteem from the public.
Design-wise, the Fifth Avenue doesn’t use any new visual elements but instead just combines features from a toolbox of tried-and-trues. The cap toe has some broguing on it, which adds a touch of ornateness without taking away from its understated charm.
It also makes it a bit more fall and winter friendly, since the detailing is in line with the textured look of cool weather looks. Think tweed, cable-knit, and brushed wool.
As always, this Fifth Avenue is made of tightly-grained full-grain leather and is bench welted all the way around. The heel, cork insoles, and leather footbed are perfectly secure, for an extra tough, resoleable, and heirloom-worthy construction.
What I Like
- Allen Edmonds is a respected American heritage brand, and the Park Avenue is a men’s footwear icon. You’ll definitely look discerning wearing this shoe around town.
- The bench welting secures the leather footbed, cork insole, and heel for extra stability, which also gives you a confident stride.
- The high-end full-grain leather build and slight broguing make for a sophisticated cool weather look.
What I Don’t Like
- In my experience, and from what I’ve read in reviews, most people experience a long break-in period.
What Do Other Reviewers Say?
From direct reviews on the Allen Edmonds website to blogs and videos all over the internet, there’s no denying that the Fifth Avenue is a well-liked shoe. Any unboxing footage will reveal reviewers immediately pleased with the sturdy feel of the sole and natural smell of the leather.
AE is another brand that gets a lot of love for their wide range of sizes. They even go all the way down to a size 5 for men.
The Verdict
If you’re looking for a forever dress shoe, the Allen Edmonds Fifth Avenue is a trusty and time-honored option. It’s refined and well-built, making the relatively high price worth it in the long run.
The subtle broguing on the cap gives it a distinguished character, while the stable wear helps you stand up a little taller. Not a bad combination.
This classy Oxford has everything you need in a dress shoe. The Oxford style closed lacing means your shoes have a slim profile that’s versatile enough for formal or casual wear.
Best Fall Suede Shoe: Grant Stone Traveler
Here’s why the Grant Stone Traveler is such an adaptable suede shoe.
At first glance, it looks like a traditional, and therefore effortlessly stylish, loafer. But those of you with a keen menswear eye might notice that it’s not exactly an American style loafer, nor is it a European style loafer.
The saddle goes down past the collar and the shoe lip is flat. It isn’t as bulky as an American loafer, especially since it lacks a beefroll, which gives it that European sleekness. However, between the suede construction and the pretty rounded edges overall, it can be worn with anything.
I’ve worn my Traveler with shorts, jeans, suits, heck I even wore it with a navy tuxedo once—big risk by the way. Check the dress code of the event you’re going to before trying that.
It’s a traditional shoe that doesn’t seem to follow any particular tradition.
Grant Stone shoes are made in China, but in a far more unique way then you’d expect from that usually alarming status. Founder Randy Gilmore worked in China for decades and has real relationships with the high-quality factories out there. By working with these literal artisans, he’s able to serve up a shoe that doesn’t use shortcuts, is fully Goodyear-welted, and is made of a special water-resistant calfskin suede.
What I Like
- The Repello suede is a unique calfskin that’s treated and processed to be extra lush and extra water resistant.
- Grant Stone’s strategic and clever business model allows them to provide Goodyear-welted shoes for far beyond the market price of comparable models.
- The unique yet still understated design can be worn with almost any outfit.
What I Don’t Like
- For the first month, it can be a bit tight when you’re pairing it with midweight socks. You might want to break it in just before the start of fall, or before it starts to get too crisp out.
What Do Other Reviewers Say?
What surprises me the most about this shoe is the intense ways reviewers have broken it in online. Everytime I write about the Traveler (which I try as often as it’s appropriate because I’m a big fan), I mention how I’ve seen videos of people putting a high pressure hose to it.
That being the case, that Repello construction is definitely as strong as advertised.
Keep in mind that Grant Stone mentions to size down for this show. I’ve seen a few reviewers complaining about the “inaccurate” sizing.
The Verdict
My go-to airport shoe, the Grant Stone Traveler is perfect for fall because the suede can handle any type of weather. It’s been treated to not only look better, but take on the elements.
Moreover, it’s Goodyear welted, and sits way below comparable designer shoes in price, and far above most shoes, quality-wise, just a touch cheaper than it.
Best Trainers for Fall: Beckett Simonon Morgen
Remember when I mentioned that items rooted in utility, particularly those with an army origin, often become closet essentials? Enter the German Army Trainer.
Another beautiful take on a classic from Beckett Simonon, their Morgen sneaker takes the stylish, multi-sectioned GAT template and builds it with water-repellent suede and full-grain leather.
Modern-day creature comforts include cloud-like padding around the collar and Vachetta leather lining. That lining, by the way, helps the footbed customize to your foot while regulating temperature, odor, and sweat. It’s a truly considerate detail to add to a casual sneaker.
Speaking of casual, here’s why I think you need a GAT for fall. It’s a less laid-back time than summer, but it doesn’t mean you’ll be wearing leather boots and loafers all season. The Morgen is made of high-class materials and features a slim toe box, giving it a level of sophistication along with its cool factor.
What I Like
- The design is accurate to a true GAT with a more refined toe box, balancing its relaxed, effortless look with a sense of class.
- The Vachetta leather lining, usually reserved for dressier models, conforms to your foot and regulates odor and temperature.
- Since Beckett Simonon partners with tanneries that are gold-rated by LWG tanneries, you can rest assured that the Italian leather is constructed with sustainability as a priority.
What I Don’t Like
Strangely, some colorways have a removable insole while others don’t. The insole is great, but some consistency is always appreciated.
What Do Other Reviewers Say?
Reviewers love how immediately soft and comfortable the Morgen is right out of the box. And while there isn’t a break-in period, it only gets softer and more customized to your foot as you wear it.
Other qualities reviewers point out is the excellent price, considering the high level of hand craftsmanship we all know Becket Simmonon is known and lauded for.
The Verdict
When choosing sneakers, it’s always fun to pick something with a cool factor. Thanks to its premium build and materials, the Beckett Simonon Morgen offers this along with refinement and trend resistance. That’s a tough combo to achieve.
Moreover, it’s wildly comfortable whether you’re stomping around city streets or kicking autumn leaves around in the woods.
Runner Up Boot: R.M Williams Craftsman Boot
Because of its utilitarian style, I think the Thursday Captain is the perfect fall boot. However, the R.M. Williams Craftsman is a better choice for you minimalists who love a good Chelsea.
It’s still slim and sleek as a Chelsea should be, but the chisel-square toe gives it a hint of workwear vibes. It doesn’t take away from the clean look overall, but instead adds a practical-looking way about it. And fall wardrobes are all about the pragmatic aesthetic.
Is it a dressy work boot or a rugged dress boot? Spoiler alert: It’s both—and highly versatile because of that.
Artisans at R.M. Williams handcraft the Craftsman right in Adelaide in Australia. It’s made from one piece of Yearling leather, which is an especially fine-grained cowhide from aged cattle. It’s known for being both supple and strong.
What I Like
- This boot is artisanal in every sense of the word, handmade in Adelaide with a luxurious and strong aged leather.
- With its chisel toe and clean look, this boot effectively straddles the dress boot and work boot categories.
- Even the innersole is premium leather, offering a supportive yet comfortable user experience.
What I Don’t Like
- I understand that the front tab is useful, but I think it’s a little much visually and takes away from the minimalism. Fortunately, you can hide it under your trousers.
What Do Other Reviewers Say?
Reviewers love the quality of the Yearling leather, reporting a buttery hand-feel and substantial weight. Of course, it has the sweet tobacco-like scent too.
Even more, many wide-footed reviewers rave over the square toe as well as the fact R.M. Williams offers this boot in a regular and wide, as well as a narrow. More traditionally-shaped Chelseas are often quite thin.
The R.M. Williams Craftsman is a distinct Chelsea in that it’s still sleek and minimal, but the square toe pushes it a bit into the work boot realm. The best of both worlds, you can wear this premium leather shoe as light workwear or as a rugged dress boot.
Best Loafers for Fall: Velasca Cadregatt
I’ve mentioned this earlier, but fall is a good time to play with a little bit of texture and detail (tweed and wool, remember?). That being the case, I love recommending a good tassel loafer for autumn wardrobes, and the Velasca Cadregatt is an exquisite specimen of the breed.
I think the Cadregatt can win over even you tassel-doubters out there, and I have two reasons why.
First of all, it’s a much more refined tassel loafer. The template silhouette gets an Italian makeover, sharpening out the toe a bit, without going razor sharp on you. This makes it more cosmopolitan than the average tassel shoe, while still maintaining its easy, unintimidating wear.
Second, you can’t argue with quality. Velasca uses a brushed calf leather, making the already fine grain of the surface even finer. Did I mention you can choose between a dressy leather sole or a comfortable and practical rubber one?
What I Like
- The combination of tassel details and a minimal loafer silhouette makes for a down-to-earth yet still graceful aesthetic.
- Though calf leather is already naturally fine-grained, Velasca uses a brushed version, making the surface look especially smooth and beautifully oiled.
- The choice between a rubber or leather outsole adds a level of useful customization.
What I Don’t Like
- This shoe is bindingly tight before you’ve broken it in.
What Do Other Reviewers Say?
As I expected, many reviewers report becoming tassel loafer converts because of the Cadregatt’s dressy shape.
A few also mention how supportive the shoe is, after it’s been broken in, of course.
On that note, almost every review I’ve read includes complaints about extreme tightness during the break-in period, so be prepared.
The Verdict
The Velasca Cadregatt is classier than the average tassel loafer, but more wearable for everyday than the average Italian dress loafer.
Construction-wise, the brushed calfskin is impeccable, while the choice between a rubber outsole or leather outsole allows you to accommodate the shoe to your lifestyle and needs.
With its sleek Italian silhouette, Velasca ups the class with their Cadregatt tassel loafer. Whether you go for the dressy leather outsole or the rubber one, the brushed calfskin upper feels delicate but is as tough as nails.
Best Moccasins for Fall: Minnetonka Classic Mocs
An Americana staple, the moccasin is to fall what the boat shoe is to summer. And with its Americana heritage, Minnetonka unsurprisingly serves up a topnotch model with their Classic Moc.
This suede shoe, which feels as soft as it looks by the way, has a ton of crossover appeal, pairing well with a camp-collar California-leaning look, a simple t-shirt and jeans combination, and of course, with a lightly or heavily textured fall palette as well. There are plenty of ways to style this moc.
The outsole is light and features gum-like rubber cleats. That being the case, you can wear this slip-resistant, bendy shoe inside or outside. I keep my pair by my door, as my quick-errand or grabbing-the-mail shoe.
What I Like
- Minnetonka uses silky, flawlessly napped suede from environmentally friendly tanneries in the Dominican Republic.
- The slip-resistant rubber outsole makes this shoe as flexible as a soccer cleat, and as comfortable as indoor footwear, making it the perfect inside-outside shoe.
- The design is an understated but distinct look, that goes well with most personal styles.
What I Don’t Like
- The thin outsole sometimes causes the collar to spread open as you move, making it look floppy. To fix this, I just tied the laces extra tightly.
What Do Other Reviewers Say?
Reviewers enjoy how easy it is to slip in and out of this moccasin. Like me, many use it as their grab-and-go shoe. The Classic Moc is also Minnetonka’s best seller.
Some mention how it makes their feet look longer because of the extra thin silhouette, but whether that’s good or bad is purely subjective. One gent writes that it sometimes makes him feel “clown-like” so that’s something to watch out for.
The Verdict
Fall is a good time to incorporate Americana pieces, and the Minnetonka Classic Moc is as quintessential as it gets. It’s also a super convenient shoe, with its comfortable and flexible rubber outsole and easy slip-on (and slip-out) design.
An effective indoor-outdoor design, the Minnetonka Classic Moc has a comfortable and bendy rubber sole and a soft suede build. Its Americana aesthetic also goes well with a range of personal styles.
How to Pick the Right Leather Color for Fall
As with any season, you’ll want to stick with colors that, more or less, occur naturally during autumn. Generally, you want to stick to earth tones and muted versions of warm colors and colors adjacent to primaries.
Go for browns, tans, olives, golds, and even navy—as long as it’s extra muted and extra cool, like the blue marino Thursday Captain that I highlighted earlier.
There are some colors that carry on from the summer into the fall, like burnt orange, that work well with shirts or accents. With leather though, you run the risk of it being too bright for the season. When in doubt, the more muted the hue of your leather, the better.
Instant Fall Classics
Now you’re ready to take on the autumn-ifying of your shoe closet.
Sneakers are a roll-over from summer, and the Beckett Simonon Reid is a classic choice, while the Morgen is as refined as it is cool.
While it may take you around three months to get your feet into these bad boys, they're well worth the wait. Made-to-order, crafted from full-grain Italian leather with a Vachetta leather lining, the Reid packs a ton of value at this price point. We also love that the eyelets are hidden to make for a slightly sleeker look overall.
Go for Grant Stone’s Traveler for a relaxed yet classy suede loafer, and Velasca’s Cadregatt for a slick take on the tassel loafer. And speaking of dress shoes, Allen Edmond’s Fifth Avenue is a fall go-to thanks to its subtle detailing.
You absolutely need a boot for the season too. Thursday Captain is a well-built service boot, while the R.M. Williams Craftsmen is best for you minimalist lovers.
Our pick of the best value service boots under $200, the Thursday Captains are made with supple, well-oiled leather and combine comfort with strength and stability. In addition to its Goodyear-welted construction and embedded steel shank, the cork midsoles will conform to your feet while the insoles are shock-absorbant.
And of course, it wouldn’t be fall without a moccasin, and Minnetonka is as authentic as they come, design-wise.
FAQs
Which shoes are suitable for autumn?
In addition to sneakers and dress shoes which are year-rounders, you’ll want to add boots to your fall rotation. Suede, especially brown suede, is also a great autumn texture that isn’t always appropriate during the summer.
Can you still wear white sneakers in the fall?
Yes, sneakers are good all year long. However, trade your light canvas sneakers for some nice leather ones.
Can I wear loafers in autumn?
Absolutely. Since loafers balance casualness and formality so perfectly, they fit that back-to-school look for all guys, whether you’re in school or not.
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