Booting Up – 15 Fall Boots That Will Make Your Sneakers Lonely

Slip-on Chelseas, ankle-length chukkas, utilitarian-meets-sneaker, modern western, and of course the classic work boot are all back in full force for fall. We have fifteen you need to make yours, as in, right now.

The summer heat may still be in full swing, but fall is just around the corner. Which means it’s time to rugged up with this season’s best boots. A/W 23 has practically a plethora of timeless pairs of quality boots that are on trend and ready to take on any adventure.

Our Editors are breaking them down, so you can break them in.


The Chelsea boot is a timeless classic that will never go out of style. Their sleek silhouette and elastic sides make them comfortable and easy to slip on and off, which was part of their original purpose – to create a boot that could be easily worn without having to lace up. These boots look great with jeans or chinos, making them the ultimate all-rounder for autumn dressing.

Blundstone has been one of the top-notch IYKYK chelsea makers since 1870. Built with the unforgiving Aussie outback in mind, they’re a favorite with farmers to fashionistas, and have a celeb cult following that includes David Beckham, Brad Pitt and Chris Pine, to name a few. The brand naturally has more than a few options, but the Original 500 is the one that started it all.

Blundstone, Original 500 Chelsea Boot $219.95

If you’re looking for something edgier, John Varvatos delivers with these multi-toned olive chelseas. Crafted from premium Italian leather with a full leather lining, these will elevate your effortless luxe-meets-rocker look.

John Varvatos, Ludlow Chelsea Boot $798

Or if you prefer a more casual approach, these easy- wearing, calfskin suede boots by J. McLaughlin are a fresh add to your footwear rotation.

J. McLaughlin, Polo Solid Crenshaw Suede Chelsea $450


For a more laidback look, turn to ankle-length chukkas. These are chunky boots that usually have two or three pairs of eyelets and an open lacing system. They are the perfect shoe for casual days out when you want to stay comfortable but still look stylish.

Made from premium Charles F Stead suede (one of the topmost quality suede out there), this brown sage pair by Clarks also sports the brand’s signature crepe rubber outsole, giving plenty of grippy feel and comfortable step.

Clarks USA, Desert Boot in Coal Sage $160

For a dressier version that can easily hold its own at business casual and even semi-formal events, Adam Derrick’s version of the chukka includes high end Italian calf leather, durable stitched, leather welts and a clean, sleek silhouette.

To Boot New York, Richard Black Chukka $450

Or if chinos and cargos are more your thing, Red Wing’s heritage chukka boot, the Weekender, is just the right mix of casual chic and comfort.

Red Wing, Heritage Weekender Chukka $289.99


Sneaker boots are high-top versions of popular sports and trail shoes. They combine the comfort of sneakers with the robustness of boots, making them perfect for the active man. Whether you’re hitting the urban jungle or a woodland trail, sneaker boots will keep your feet warm, comfortable, and stylish. Their athletic design pairs well with jeans and joggers, offering a casual yet trendy look.

These Pampa Hi from Palladium Boots understood the assignment completely. A lightweight and comfortable washed canvas upper is combined with the brand’s thick, trademark lug sole. Of course, adding an ergo EVA footbed will keep your feet happy all day and the classic black-on-black will go with just about everything in your pants drawer.

Palladium Boots, Pampa HI $85

For an more rugged look, Nike’s Woodside 2 High ACG takes the brand’s high-top silhouette and then adds a water-resistant upper and soft, warm lining for lasting comfort. Plus the thick rubber overlay adds durability, and of course, the stylish logo in leather brings the whole thing together.

Nike, Woodside 2 High ACG Boot $125


The rise of utilitarian fashion has elevated the humble hiking boot higher than the K2. Moreover, it’s mainstreamed into just about everything from streetwear to off-duty, to preppy, to just about everything.

Like these ultra-lightweight boots from Palladium in minimalist-loving white. It’s a perfect fusion of tech, fashion and function.

Palladium Boots, Pampa Travel Lite $110

From the G.H. Bass archives comes this handsome hiker called the 1876, which looks right at home with your 501s as they do with your selvedge slim-fits.

G.H. Bass, 1876 Alpine Hiker $365


Nothing says classic cowboy style quite like a pair of modern western boots. These ankle-length boots feature a pointed toe and chunky heel, perfect for making a statement. Whether you’re dressing up or down, these boots will always add a touch of western flair to your look.

When in doubt, go timeless. These taupey, roughout leather boots by Ariat are just that, along with some modern upgrades such as an AST midsole balance cushion to give some ergo-comfort in every step.

Ariat, Downtown Western Boot $259.95

With its shorter silhouette, this bootie gives a more modern approach, but still keeps things familiar with a classic Cuban heel.

Sonora, Hidalgo Suede Ankle Boot $565


Finally, classic work boots are the ideal option for rugged outdoor adventures. These enduringly stylish boots provide excellent protection from the elements and many feature a reinforced toe cap to keep your feet safe when you’re out exploring. No matter what activities you have planned this season, these boots will make sure that your feet stay comfortable and supported all day long.

Handmade by generations of Italian family crafters, the Gregorio is a boot made from Italian calf leather that gives it an instantly soft feel that wears like iron. All the bells and whistles are here, like speed hooks up top, waxed cotton laces and a lightweight rubber sole. These handsome fellows will finish off any off-duty look you have.

M. Gemi, The Gregorio $278

(on Sale NOW from $378)

With it’s Extralight® EVA Outsole and slip resistant treads, the Ranger work boot by G.H. Bass will ensure smooth passage over those slick, sleety, late autumn streets.

G.H. Bass, Leather Ranger Super Lug Boot $225

And finally, we have the OG streetwear-loving working boot – the waterproof Timberland. Designed more than 40 years ago and remains a best-seller today, this instantly recognizable work-boot will give your baggy jeans instant drip.

Timberland, 6-Inch Premium Boots $159.98

(on Sale NOW from $198)

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