The Best Fall Shoes: Trends, Classics, Everything You Need

Going from summer to fall requires a bigger overhaul than the spring-to-summer transition before it. Here are the best fall shoes you’ll need this year!

Fall is a great time for menswear. Peacoats, tweed, suede, browns, and navy are all flattering classics. But remember, your footwear can make or break your outfit. So, as you transition your wardrobe, it’s important to consider the best fall shoes in 2024. 

Early autumn is dramatically warmer and less gray than late fall. Sometimes, there’s an overlap between your fall-time shoes and what you’ll need for winter. I know it sounds like there’s a lot to consider, which is why I’m here to help. 

Let’s start with the fall 2024 shoe trends.

Fall 2024 Shoe Trends

Fortunately, a lot of the trends we’re expecting are looking pretty classic. If I learned anything from the fall lines at New York and Paris Fashion Week, it’s that traditional menswear is back. 

One of the footwear trends you’ll see is the return of the cowboy boot. You don’t even need to have an especially cowboy-leaning style to sport them. A flannel, jeans, and cowboy boots are more fashion-forward than if you wore neutral work boots.

Another trend we’re expecting is the chic-ification of work boots. Think strong, well-lugged, thick-collared boots. However, they’re not as clunky and boast cool, dark colors. The Thursday Boots Commander is a great example of this.

Two-tone shoes will likely move from the runway to the masses. Ralph Lauren’s Leather & Wool Cap Toe combines elements that are classic but don’t usually go together. If you want to experiment with this trend but don’t want to commit, there’s always Amazon. They have a cheap two-tone dress shoe that you can use as a test drive.

Alright, on to casual shoes for fall.

Casual Shoes for Fall

I wouldn’t put your low-profile white sneakers away just yet. But you’ll want to add some dark sneakers and fall slip-ons to your range.

Fall Sneakers

Brown leather sneakers are a great choice for fall.

They combine the cool, casualness of a trainer with a classic Americana style and a touch of dressiness. 

Budget Pick: Banana Republic Vegan Leather Sneakers

Ok, the downside to these sneakers is that vegan leather doesn’t last as long. The upside is that it’s more environmentally friendly, it looks great, and it’s comfortable right away. Even more, at less than $50, you’ll get your money’s worth.

Value Pick: Oliver Cabel Low 1 Lion

This stylish sneaker‘s elegant full-grain leather contrasts excellently with the white outsole, making it highly versatile. Plus, the Italian leather, organic lining, and calfskin counters offer an excellent value proposition.

Splurge Pick: Koio Capri Mocha

What I love about the Koio Capris is that they’re a splurge, but not really that much of a splurge for what they are. These are hand-made in Tuscany using vegetable-tanned Italian leather. The waxes and oils provide a beautiful, luxurious sheen.

Mocassins and Slip-Ons

Yes, you still need slip-ons in the fall.

In fact, pairing them with thick socks is both practical and gives a cozy yet classy look.

Value Pick: Minnetonka Pile Lined Hardsole

The value pick is also the most casual pick. This Pile Line is just a hard-soled version of their indoor variant. It has that cozy vibe I mentioned.

The lining is also perfect for going sockless on warmer days. And if anyone knows how to put together a genuine moccasin, Minnetonka does.

Value Pick: Sperry Classic Boat Shoes with Lugs

How do you take a summer classic into the fall? Easy. You go for the lugged version. It’s coastal cool meets workwear ruggedness in fall tones. 

Splurge Pick: Rancourt&Co Gilman Camp Moc

If you want a proper, full-grain leather moc, I recommend Rancourt & Co. They’re elegantly simple, hand-made in Maine, and would look just as nice with shorts and a t-shirt as they would with a blazer.

Dress Boots

Classic lace-up boots get a lot of mileage in a men’s fall wardrobe.

They’re an important part of your shoe closet.

Budget Pick: Eastland High Fidelity Cap Toe

We’ve recommended these boots in the past, and that’s because finding a good leather boot on a budget is hard. For around $100, this cap toe looks the part and needs little to no break-in.

Value Pick: Thursday Boots President

What impresses me most about the President isn’t its strong leather or handsome design. It’s the Goodyear welted construction — not too shabby for a sub-$200 boot.

Splurge Pick: Grant Stone Diesel Boot

The Diesel is both classic and distinct and combines style with function. This Goodyear-welted boot has a steel shank and cork filling, providing comfort and stability. 

A Casual Statement Shoe

Okay, so you don’t need a casual statement shoe. That being the case, I’m only going to recommend one: The admittedly splurgy Dries Van Noten Suede Sneakers. If you’re going to go statement, go quality.

Dries Van Noten Suede Sneakers

Making a statement with your shoes doesn’t mean finding something loud or overly weird. Mixed textures, shades of green, and accent pops are enough to do the job. Plus, these features are all fall staples. The Dries Van Noten Sneakers encapsulate all of these style tenets.

Nice Fall Shoes: Boots and Dress Shoes

Dress shoes are year-rounders, so don’t put those Oxfords and loafers in storage. They’re great fall shoes. But let’s add some boots and bluchers to the rotation.

Bluchers

Bluchers are an open-laced shoe, like derbies. However, since they’re made with one cut, they look cleaner. This balance of ruggedness and dressiness is perfect for fall.

Budget Pick: Eastland Buck

The Buck shoe is another model we’ve recommended in the past. It’s good for the price, comfortable out of the box, and has an attractive red outsole which is nicely seasonal.

Value Pick: Beckett Simonon Sutton

Are you willing to pay with time instead of money? Made-to-orders can take months to ship, but the Sutton boasts the quality of a shoe three times its price. 

Splurge Pick: Allen Edmonds Leeds Shell Cordovan

The shell cordovan that this Leeds shoe is made from is truly remarkable. It’s especially strong and supple. It ripples isntead of creases, building character instead of flaws over time. And the natural gloss provides vivid color.

Chukka Boots

Chukka boots are classy but casual, with an equestrian vibe.

They’re also a fall staple.

Budget Pick: Johnston & Murphy Upton Shearling

Though this budget boot has a budget build, it looks good and gets the job done. The shearling lining proves especially useful in late fall.

Value Pick: Thursday Boots Scout

This solidly-built chukka comes in a world of colorways, all of which would work beautifully in fall and winter.

Splurge Pick: Velasca Artista

Supple yet strong calf leather, unique color options, and modest-man-friendly sizing make this boot my go-to choice for luxury chukkas.

Chelsea Boots

For a more urban, mod boot, try Chelsea boots over chukkas.

As an added plus, they easily slip on and off. 

Budget Pick: New Republic Sonoma

The Sonoma is that rare decently-built boot for well under $100. Its crepe sole gives it a desert aesthetic that even works in the summer.

Value Pick: Thursday Boots Cavalier

Once again, Thursday gets my pick for value. And once again it’s in large part thanks to its Goodyear welting partnered with a sub-$200 price tag.

Splurge Pick: Carmina Rain

If your budget allows, you might want to try these super dressy, extra chic, hand-made Chelseas. The stacked heel and incredible leather match the sleek, European silhouette.

FAQs

Here are some FAQs about fall footwear!

What shoes are best for cold weather?

Dark colors and leather are best. The colder the weather, the higher the shoe collar should be. Lined, leather, lugged moccasins are great for moderate fall days, while boots are ideal for extra-cold days.

What dress shoes are best to wear in winter?

Go for dark-colored, full-grain leather, Goodyear-welted shoes, as they’re more weather-resistant.

How many shoes do I need for the fall and winter?

You’ll need casual shoes, like leather sneakers, classic dress shoes, and heavy-duty boots for intense winter days.

Conclusion: A Good Season for Men’s Shoes

Fall combines practicality with style, which is why I always say it’s the best season for men’s fashion.

This is especially so with outerwear and shoes. If you want to go capsule, just make sure you have dark sneakers, a pair of dress shoes, and good boots.

What are your favorite fall shoes? Let me know in the comments!