5 Boots You Need for Fall
Bring your boots game up a level with these new-in fall styles.
By: Harry Rosen StaffDate: 2026-09-15
When you think about fall footwear, boots always spring to mind first. However, there’s an art to finding the perfect fall boot — you need something robust-yet-refined, sturdy-yet-stylish, comfortable-yet-chic. Unfortunately, many miss the mark on one or more of those criteria.
From lace-ups to slip-ons, smooth leather to suede, take confidence in your footwear rotation this season with these standout boots made for fall.
Anatomia 013 Leather Ankle Boots, Officine Creative
If you had to have just one style of boot for fall, make it a classic leather lace-up — like these from Officine Creative. Versatile enough to dress up or down, for work or weekend, they’re the ultimate do-it-all boot for between seasons.
Made in Italy from soft brown Buffalo leather featuring classic details like D-ring speed hooks and a stacked leather sole, they’re a timeless choice that will only get better year after year.
Roger Vibram Suede Lug Boots, Barrett
Suede is a quintessential fall material, and every man needs a pair of suede boots in his autumnal rotation. We love these from specialist shoemakers Barrett for their soft mid-brown upper, sturdy Vibram lug-sole, and apron toe — details you don’t always find combined into one boot.
Oh, and the fact they’re Italian-made doesn’t hurt either; a mark of quality that extends far beyond just aesthetics.
Suede pairs naturally with other tactile fall fabrics like denim, flannel wool, and leather. Lean into the rich mid-brown tone by pairing these boots with earthy neutrals, deep navy, or grey for an effortlessly seasonal look.
Ventura Quintessenza Suede Hiking Boots, Pajar
Based on the classic hiker-style boots made popular by adventurers of decades past, this handsome suede variation from Pajar offers a refined update made for the contemporary globetrotter. A true wardrobe chameleon, you can ask almost anything of these boots.
The versatile grey colour works with essentially every other colour, and the water-repellent, seam-sealed construction means rain, sleet, or even snow is no concern. While they're proudly made in Italy, they look (and feel) equally at home anywhere you wear them.
Boots with chunkier soles and silhouettes work best with wider trouser openings and fuller breaks. Read our guide to how pants should fit to learn more.
Suede Desert Boots, Ferragamo
The Desert Boot (aka chukka) style evolved from ankle-high boots worn by polo players during the late 19th and early 20th centuries, and has remained a menswear staple ever since.
This modern interpretation from luxury house Ferragamo features contemporary details including a stacked heel, grippy Vibram sole, and mid-grey calfskin suede upper. We love these for their sharp last and toe shape, soft calf leather lining, and superior Italian craftsmanship, culminating in a boot as refined as it is versatile, equally at home on city sidewalks and country roads.
Desert Boots are an inherently more casual style that looks best when worn with jeans, chinos, or 5-pocket pants.
Easy Leather Chelsea Boots, Santoni
No fall footwear edit is complete without a Chelsea boot — an iconic style made globally popular in the 1960s that still looks as sharp and relevant as ever. The beauty is in the simplicity — slip on, slip off, no laces required.
That said, these Chelsea boots from Santoni offer far more than just ease (though it's fitting they're part of the brand's Easy Collection). Hand-crafted in Italy, these lightweight, pebbled leather boots feature a memory foam insole, perforated Nappa lining, and an understated yet durable rubber sole.
Chelsea boots' biggest claim to fame came from being The Beatles' favoured style of shoe — which means slim-cut suits and classic Mod style are their most natural pairing.
Not all boots (or all brands) fit the same, and the best way to ensure you get it right the first time is to try them on yourself.
For one-to-one sizing and style advice, with an expert Style Advisor at your nearest Harry Rosen location, or pop by the next time you’re in the area.
Stride in Style
