Reviewed & updated: September 11, 2023 by Jamie Wilson BA
Fall is a godsend for men who appreciate a solid wardrobe. Why? This season is the Super Bowl of menswear, wildly when kicking your shoe game up a notch. In this article, we’re breaking down the top fall shoe options that should be on your radar so your feet don’t freeze off and you don’t get caught looking like you stepped out of last season.
Let’s clarify: When the leaves start falling, so should your flip-flops—into the trash. This is the season to strut your stuff in layered outfits complemented by shoes that scream style and substance. And if you’ve been clinging onto that summer tee like it’s a life raft, it’s time to let go and embrace the chunkier, cozier, and infinitely more exciting wardrobe options that fall brings. Ready to step into the season with swagger? Keep reading.
The Perfect Fall Footwear Guide for Men
Fall is more than a spectacle of falling leaves and pumpkin-spiced everything; it’s the Super Bowl season for men’s fashion. Your shoe game this season should be nothing short of legendary. We’re going beyond the basics like “brown boots are good” to provide a comprehensive rundown of the best options. Trust us, there’s more to explore than just a pair of everyday boots. Ready? Let’s get into it.
The Fundamentals: What Makes a Fall Shoe Stand Out?
Come autumn, your gear’s got a different vibe. We’re talking vests, cardigans, and jackets layered up like you’re making a clothing lasagna. Fall is the domain of heavier fabrics—wool, corduroy, and flannel. So, your kicks should fit right into this textured, chunky landscape. Brown boots are a go-to, but what about sneakers or loafers? Versatility is key, my friends.
Chukka boots offer various options, from leather to suede, casual to dressy. Whether it’s brown leather for everyday wear or grey suede for a change-up, these boots mesh well with your relaxed and snappy outfits.
Originating from WWII British desert boots, the Bushacre gives you a timeless look without breaking the bank.
Thursday Boots Scout
This versatile chukka slots right in the middle when it comes to formality. Pair it with chinos and a button-down, and you’re good to go.
Ace Marks Lorenzo Chukka
When a suit calls, answer with these Italian calfskin beauties that pack durability without sacrificing style.
With all that layering up top, you need something substantial below to keep the balance. Leather lace-up boots fit the bill. Think of them as the wingman to your henleys, flannels, and leather jackets.
Clarks Bushacre Eastland High Fidelity Cap Toe
A budget-friendly boot that holds its own, especially if you temper your expectations.
Thursday Boots Captain
The Captain offers quality and comfort at a price that won’t force you to sell your car.
Grant Stone Diesel
These boots are a long-term investment in quality. They’ll hold up, season after season.
Let’s say you’re not in a booty mood. Moccasins offer a laid-back alternative that pairs well with casual outfits, especially when reaching for those thick wool socks.
Minnetonka Camp Moc
Great for casual wear and a solid alternative to boat shoes during the warmer seasons.
L.L Bean Jackman Ranger Moc
If you’re a boot guy looking to try something different, these mocs are your gateway.
Clarks Bushacre Rancourt & Co.
Handmade in Maine and built to last, these are for those who want to invest in top-notch quality.
Brown Minimal Sneakers
White sneakers might be the summer staple, but consider flipping the script with a brown minimalist pair as the leaves change. Whether it’s a gum or white sole, brown works like a charm when the temperature dips.
Cole Haan Grand Crosscourt
Available for around 50 bucks on Amazon, these leather sneakers offer solid value. They sport a low-profile design that matches pricier high-end models, minus the wallet pinch.
Beckett Simonon Reid
Handcrafted leather under $200? Sign us up. Beckett Simonon’s Reid stands out with its pebbled texture, ideal for the fall. Just note these are made-to-order, so patience is vital. For a faster option, look no further than the Greats Royale.
Koio Capri Mocha
If you want to splurge, these sneakers are well worth the investment. Premium quality, enduring design, and the Mocha hue scream sophistication.
Trainers nail the casual vibe for quick errands or a chill day out. Chunkier options like New Balance add an extra kick when paired with jeans or chinos.
Onitsuka Tiger Mexico 66
Drawing inspiration from German Army Trainers, these low-profile sneakers offer endless color choices. Consider shades like tan/brown or burgundy/white for an autumn twist.
New Balance 574 V2
The modern version of a classic, New Balance’s 574 V2, is a colorful essential. Opt for the more prosperous, darker color schemes to make a seasonal statement.
From a laid-back pub crawl to a snazzy dinner date, Chelsea boots are your best mate. They bring the heat in style and function, pairing well with a range of pants.
Solid style, quality, and affordability coalesce in New Republic’s offering. These boots could be the best bang for your buck regarding affordable Chelsea.
Comfort is the name of the game with Amberjack. The cushioned feel almost makes you forget you’re wearing a boot. The lack of a pull tab offers a smoother aesthetic.
Thursday Boots Duke
For sub-$200, you get Goodyear-welted quality and style. Ideal with denim or chinos, the Duke is more of a casual Chelsea — not the one for your tux, but perfect for most other occasions.
Bluchers scream classic, but with a suede texture, they can blend seamlessly in a more relaxed office setting.
Eastland Buck Oxford
Affordable yet stylish, Eastland’s Buck is your entry point into the world of bluchers. The brick-red outsole adds a dash of character.
Beckett Simonon Dunham Derby
With a two-month wait time, anticipation builds for this quality pick. Either chestnut or brown color brings a sophisticated balance to any non-black pants in your wardrobe.
Grant Stone Longwing
If you’re going premium, Grant Stone delivers. Their Longwing blucher brings sophisticated broguing and quality that rivals brands like Allen Edmonds.
Dress boots aren’t just a cold-weather game-changer; they’re timeless additions to any man’s wardrobe. Offering warmth and elevated style, they’re the boots you’ll want to lace up or zip into when temperatures drop.
Rockport Colden Wingtip
Let’s get this straight: Rockport is the comfy granddad of dress boots. While they might not be a marvel of high-quality leather or boast Goodyear-welt construction, the Colden Wingtips give you decent style at under a hundred bucks. And they break in faster than you can say, ‘Fall is here.’
Beckett Simonon Elliot
We’re not just fans of Beckett Simonon; we’re devotees. Their Elliot Balmoral Boots are bang-for-your-buck champs at under $250. Timeless but never dull, these boots can pivot from wool trousers to chinos without sweat. Wear them with a suit; the Oxford construction and leather outsole won’t disappoint you.
Allen Edmonds Dalton
When you’re set on making heads turn, the Dalton by Allen Edmonds should be your go-to. Not for the frugal, but hey, quality comes at a price. Wingtip design? Check. American craftsmanship? Double-check. You’re not just buying a boot; you’re making an investment.
Hold up; before you pack away your loafers for the winter, consider giving them a fall revival. Pair them with wool socks and watch your style elevate effortlessly.
G.H. Bass Weejuns
Call ’em classics or timeless—either way, the Weejuns by G.H. Bass are your jack-of-all-trades loafers. Perfectly acceptable from casual Fridays to Sunday brunch. Just don’t attempt to pull them off at black-tie events.
Jay Butler Millbank Bit Loafer
Bit loafers are like the cooler older cousin of the standard penny loafer. Jay Butler specializes in this arena, and their Millbank Bit Loafer is the best you’ll snag for under $200. And those olive and burgundy options? Fall fashion stamped and approved.
Do you want to talk premium? M.Gemi’s Sacca loafers are a cut above. Crafted in Italy, these suede beauties feel like walking on air, especially when paired with thick wool socks. But heed this: These loafers are snow’s worst enemy.
When you need something less formal than boots but equally stylish, high-top sneakers have your back. And yes, keep the shorts for the summer.
Cole Haan Grand Crosscourt
Under $100 for leather high-tops? Cole Haan’s Grand Crosscourt isn’t just a bargain; it’s a steal. Especially in lighter brown shades, they bring a warm touch to any fall outfit.
Greats Royale High
If your budget can stretch, the Greats Royale High offers Italian craftsmanship for around $150 when on sale. Premium leather and a bang-on design make these an irresistible buy.
The Primo by Koio is the epitome of a luxury sneaker. From the immaculate silhouette to the hand-painted edges, you’re looking at a masterpiece. Sure, it’ll dent your wallet, but are they worth it.
Long gone are the days when mules were a fashion faux pas. Whether it’s wool, suede, or even eco-friendly materials, mules have broken into the mainstream and made themselves at home—literally.
Birkenstock Boston Clogs
The adaptable Boston clogs by Birkenstock are iconic for a reason. Slide into these, and you’re suitable for all seasons, not just the fall.
Autumn is your playground when you’re game to embrace the ‘gorpcore’ look. Chunky midsoles and tech-focused materials make trail shoes the missing puzzle in your rugged, outdoor look.
Salomon ACS Pro Advanced
High-tech and high-style, Salomon’s ACS Pro Advanced trail shoes are more than just a fad. Breathable, durable, and loaded with grip, they’re as functional as they are fashionable.
So, this fall shoe guide covers you, whether it’s the office or an outdoor adventure. From trail shoes to dress boots, stepping up your shoe game has never been more straightforward—or more stylish.
What Are The Best Fall Shoe Options For Men?
Alright, fellas, let’s talk autumn footwear. You know, the shoes that’ll carry you through those leaf-crunching, cider-sipping days. Here are some of your best bets:
- Rockport Colden Wingtip – Budget-friendly and comfortable, but expect them to last only a short time. Still, they’re a solid choice for under $100.
- Beckett Simonon Elliot – Quality and style under $250. Timeless yet contemporary, they can level up jeans, chinos, or a suit.
- Allen Edmonds Dalton – The showstopper. If you want to invest in a top-tier, long-lasting pair, these wingtips will always be there for you.
- G.H. Bass Weejuns – The classic penny loafers are versatile enough for most casual and semi-casual outfits.
- Jay Butler Millbank Bit Loafer – For those looking to add a bit of flair, these bit loafers are a step up from your typical loafers and under $200.
- M.Gemi Sacca – Luxury Italian suede, perfect for fall but not for heavy winter conditions.
High Top Sneakers
- Cole Haan Grand Crosscourt – It’s a budget-friendly pick that doesn’t skimp on style, especially in earthy tones.
- Greats Royale High – Premium materials and Italian craftsmanship under $200—if you catch them on sale.
- Koio Primo – If you’re willing to splurge, these are the crème de la crème of high tops.
Mules and Clogs
- Birkenstock Boston – Comfortable, year-round classics. It’s ideal for those chill at-home days and a quick dash to the store.
- Salomon ACS Pro Advanced – Sturdy, tech-heavy shoes that are just as home on the trails as they are in a fashion-forward outfit.
What Makes A Fall Shoe Stand Out?
When nailing your fall footwear, key factors separate the outstanding choices from the mediocre. Here’s what makes a fall shoe really stand out:
Fall is that unpredictable season where it can be sunny one moment and pouring rain the next. Your shoes should be able to navigate this fluctuating weather and mesh well with a range of outfits. A versatile pair can transition smoothly from the office to a night out or a weekend stroll through the park.
Gone are the summer days of canvas and flip-flops. In the fall, you want materials like quality leather or suede that are durable and can withstand moisture. Suitable materials elevate the look and make your investment go a long way.
We’re talking about shoes you’ll wear as you navigate apple orchards, football games, or long scenic drives. Comfort is non-negotiable. Look for cushioned insoles, arch support, and a snug but not tight fit.
Let’s be honest: They’ve got to look good. Whether it’s a sleek minimalist design for the modern man or a rustic aesthetic for the guy who loves timeless classics, the visual element has to click with your personal style.
Fall is all about those warm, earthy tones. Think browns, deep reds, and dark greens. While you can never go wrong with black or white, embracing seasonal colors can make your outfit and shoe game pop.
Little features like water resistance, breathable lining, or a sturdy grip can make all the difference in your daily wear. You want shoes that are as functional as they are fashionable.
So, when shopping for that perfect pair, remember these points. The best fall shoes will tick most, if not all, of these boxes, ensuring that you look good, feel good, and are prepared for whatever the season throws your way.
What Are Some Alternatives To Boots For Fall Footwear?
Stepping into fall doesn’t necessarily mean you have to default to boots. There are plenty of alternatives that offer style, comfort, and functionality. Let’s break it down:
A solid pair of leather or suede sneakers can be a great alternative to boots. Opt for darker, muted colors like brown, grey, or navy to vibe with the season’s palette. High tops, in particular, offer a bit more ankle coverage for those crisp mornings. Brands like Cole Haan, Koio, and Greats are worth checking out.
Yes, the right pair of loafers can indeed work for fall. You’ll want a more robust material, like thicker leather or suede. A tassel or horse-bit detail can add a touch of style and be rocked with wool socks for added warmth. Think G.H. Bass or Jay Butler for budget-friendly options and M.Gemi for a splurge.
Derbies and Oxfords
These are the workhorses of a man’s shoe arsenal. Look for versions with a chunkier sole for a bit more substance and casual touch for fall. Stick with darker shades or use a two-tone or wingtip style for added interest. Brands like Allen Edmonds offer excellent craftsmanship and durability.
Mules and Clogs
Yes, you read that right. While not your traditional fall footwear, a solid pair of mules or clogs can keep you comfortable both indoors and for quick errands outside. Brands like BIRKENSTOCK offer clogs with adaptable straps and solid footbeds, perfect for the guy who values comfort but wants to maintain style.
If you’re adventurous, a pair of trail shoes can be a surprisingly stylish alternative. Look for options with strong grips, breathable material, and a color scheme that works with your wardrobe. Salomon offers great functional choices that make sure to match style.
Each alternative offers a unique blend of style and function without making you resort to the boot section. So explore these options and add some versatility to your fall footwear game.
Alright, gents, there you have a comprehensive guide to kick up your shoe game this fall. Whether you’re out to make a statement with a classy pair of dress boots or embracing the outdoor vibe with rugged trail shoes, the key is to match your style with the season and occasion. Don’t forget, though, sometimes you get what you pay for, so know when to splurge and when to save. The real risk is sticking to what you know and never experimenting with new styles. Shoes are more than just foot coverings; they’re the foundation of your look. So don’t let the season pass without trying something new. Trust me, your wardrobe will thank you. Now, go out there and step up your game.