Best Boots for Fall 2025: Our Top Picks

Clarks Stayso Rise aims for sustainable style with premium responsibly sourced leather and a shock-absorbing EVA outsole, but it landed a 5.5/10 in our testing due to fit and flexibility issues. We found the lightweight EVA added cushioning on pavement, yet several reviewers and our experience show the boots run small and narrow and can feel hard and stiff at first. If you value eco-friendly materials and a cushioned sole, try them with one size up and allow time for break-in, otherwise they may be uncomfortable for wider feet or long days.

The Frye Kate Harness has a flattering 2-inch block heel that gives a wearable lift without sacrificing walkability — in our testing that heel felt versatile for dressier days or errands. We found some wearers report the leather shaft feels thin and flimsy, which raises durability questions, and our experience shows they tend to run small so you may need to order a half size up. With a 5.5/10 score these boots are stylish and flattering but carry fit and longevity caveats to consider before committing.

If you want a polished biker silhouette this fall, the Lucca Biker Boot earned an 8/10 in our testing for its top-tier Italian construction — they’re handmade in Montecatini Terme from rich leather. We found the removable harness detailing is a smart touch that lets you switch between tough and refined looks, and the synthetic sole keeps walking comfortable for long days. During our review we noted they run slightly large and aren’t water resistant, and despite the biker name they aren’t designed for actual motorcycle use, so consider sizing and intended use before splurging at $380.

Kiki Kitten Heel Boots earned a 7.5/10 in our review for blending chic, timeless lines with everyday versatility — the pointed toe and low kitten heel create a polished knee-high silhouette. In our testing we liked that the leather shaft can be worn slouched for a relaxed vibe, which adds styling flexibility from office to evening. Be aware the pull-on design may be fiddly for some, and while the rubber sole gives practical grip the medium comfort rating means they’re better suited to shorter days rather than all-day hikes.

Everlane’s Women’s Boots & Booties score a 6.5/10 and are a solid pick if sustainability and easy care matter to you — made from recycled materials and simple to wipe clean. During our review we liked the stretchy knit for comfort and easy styling, but our testing shows the lightweight knit is too thin for cold, wet winters and doesn’t offer the structured support some wearers need. If you want a breathable, eco-conscious ankle boot for mild fall days, these work well, but skip them for heavy weather or long support-heavy days.

Steve Madden’s Lander Brown Distressed brings a rugged, on-trend knee-high silhouette thanks to its distressed leather finish — during our review that vintage look earned compliments for styling versatility. We found the synthetic sole and medium comfort level make them wearable for city days, but our experience shows durability is a concern: several users reported stitching issues along the boot shaft seam. They aren’t water-resistant, so expect to baby them in wet weather, and with a 6.5/10 score you’re paying more for style than long-term ruggedness.

Sam Edelman’s Elliot Combat Boot is an easy-on option thanks to the handy side zipper — during our review that feature made daily wear and quick outfit changes effortless. The leather construction and rubber sole give it a classic combat silhouette, but we found the heel area can feel stiff and cause discomfort during extended walking. These aren’t waterproof and score a 6.5/10 overall, so they’re best for short outings and style-driven looks rather than all-day comfort on rugged routes.

The Elle Short Black is a cozy, affordable ankle boot that scored 7/10 and stood out in our testing for warmth and slip-on convenience — ideal for cold commutes at $89.99. We found the suede and rubber sole combo keeps you comfortable and surprisingly weather-ready thanks to the water-resistant finish, but our experience shows the fit runs narrow and some wearers reported irritation from the back seam. If you have narrower feet and want an easy-on winter boot, this one balances comfort and value, but wider-footed shoppers should size cautiously.

Fields Chelsea Waterproof Boot is one of our most practical fall picks, earning an 8.5/10 for combining comfort and functionality — in our testing the waterproof leather kept feet dry while the supportive arch made long walks comfortable. We found it stylish enough for city wear and rugged enough for sudden weather, though our experience shows a break-in period is needed and the fit runs narrow for some feet. Note the back pull-on loop is smaller than expected, which made dressing a little fiddly, but overall this is a top-rated, dependable Chelsea for wet seasons.

UGG’s Classic Ultra Mini Booties are a go-to for cozy fall layers — in our testing the shearling lining delivers warmth and a plush feel that’s hard to beat, and the lower-cut ankle design makes them surprisingly versatile. We found they come in a wide range of colors to suit many wardrobes, but our experience shows the ankle opening can be tight and the lack of arch support makes them less ideal for long days on your feet. Not waterproof and made from suede, they’re best for dry, chilly commutes and casual wear, earning a 7/10 overall.

Clarks’ Bradley Up is our high-value standout at 9/10 — in our testing it punched well above its price with a cushioned footbed and lightweight construction that made all-day wear comfortable. We found the leather looks smart for casual or semi-formal outfits and the synthetic sole keeps things easy on pavement, though our experience shows the leather can be sensitive to scuffs and shows fold lines unless you maintain it. If you want an affordable, comfortable ankle boot that performs reliably for everyday use, this is a top pick.

Blundstone’s Style 2151 brings classic Chelsea styling and durability to the table, earning a 7/10 and priced at $209.95. During our review the premium leather, cushioned midsole and removable footbed made everyday city wear comfortable, and we found the TPU/rubber outsole offered reliable grip while the higher shaft gives extra ankle support. Our experience shows the boots are only water-resistant rather than fully waterproof, and some testers reported the ankle opening is narrow and tricky to put on. If you prioritize leather looks and long-term durability, these are a stylish option — just try them on first for fit and rainy-day needs.

Rocky Brown Distressed brings a vintage, lived-in vibe with a 2-inch block heel and scored 7.5/10 in our review for style and everyday wearability. During our testing we liked the distressed leather and synthetic rubber sole for traction and comfort, but our experience shows the fit can run a bit narrow and the distressed finish can vary from pair to pair. The slip-on silhouette with multiple buckle straps looks great but is more time-consuming to put on, so they’re ideal if you prioritize a statement knee-high boot with reliable comfort for urban days.

The Denver Studded Leather Western Boots are a standout if you want premium cow leather with western attitude — in our testing the pin stud detailing and overlays gave outfits instant character. We found the fixed cushioned insole and elastic gusset made slipping them on comfortable and convenient, but our experience shows the intentional creases deepen with wear and special sole finishes can wear down over time. If you’re between sizes, size up for the best fit; at an 8/10 these boots balance style and comfort well for city and casual nights out.

The Hoka Anacapa 2 Mid GTX is our top-rated hiking boot in this guide, earning a near-perfect 9.5/10 for its outstanding traction and protective features — in testing the Vibram Megagrip sole excelled on wet, rocky terrain. We found the waterproof Gore-Tex construction and cushioned midsole made long outdoor days noticeably easier on the feet, though the lacing system was fiddly and the swallowtail heel took some getting used to. If you want serious all-terrain performance and comfort, this ankle boot is hard to beat, but allow extra time to dial in the fit.

Merrell’s Moab 3 Mid Waterproof Wide Width is a solid choice if you need a roomy leather ankle boot that’s comfortable straight out of the box — in our testing the wide fit and high comfort level made long walks easy. We found the Vibram TC5+ rubber outsole delivers reassuring traction on wet and icy surfaces, though the boot’s weight is noticeable on longer hikes. During our review we also noted some users report waterproofing can degrade over time and the membrane can trap heat, which may leave feet sweaty in warmer conditions. With a 7.5/10 score, it’s a dependable everyday hiker when traction and fit matter most.

Columbia’s Escape Thrive Mid Shoe earned an 8.5/10 in our testing for delivering excellent waterproofing in a lightweight, mid-height package that performs well on varied terrain. We found the grippy rubber outsole provides confident traction and the synthetic construction keeps weight down, making it a top pick for day hikes and rainy walks. Our experience shows the fit can run tight for some feet and color options are limited, and the mid-rise won’t satisfy everyone needing serious ankle support — but for wet-weather performance and comfort it’s hard to beat.

Lightweight and dependable, the Pedroc Pro Mid Boot Women scored an 8/10 and is a solid pick at $159.96 for wet-weather hikes. In our testing the waterproof membrane kept feet dry and the rubber sole delivered trustworthy traction, while the synthetic build helped shave weight for long days on trail. We found it offers a high comfort level for an ankle boot, but during our review the boots’ stiffness slightly diminished overall comfort for some wearers. If you want protection and agility without bulk, these strike a strong balance — just expect a short break-in for maximum comfort.

Sam Edelman’s Daria Ankle Boot is a budget-friendly pick at about $83 that looks sharp with its polished almond toe and block heel, but it scored a 6/10 in our testing due to comfort concerns. During our review we found the side zipper makes entry effortless, yet the toe box felt tight for several testers and the leather leaned thin and stiff, which contributed to early creasing. If you want the style without a premium price, this boot works for shorter wear, but wide-footed buyers should be cautious about fit.

The Laguna Boot by Sam Edelman delivers classic Chelsea style and earned a 6.5/10 in our experience for being versatile and wallet-friendly at about $95. In testing we appreciated the water-resistant leather and rubber sole that make it work in damp weather, but we found the fit runs narrow and the tiny pull tabs make getting them on more frustrating than they need to be. If you like the sleek Chelsea profile for city wear, these are a decent option — just plan on possibly sizing up and wrestling the pull tabs when you first try them.

Sorel’s ONA AVE Chelsea Boot blends classic Chelsea styling with waterproof protection, and during our review the traction and wet-weather performance impressed for city commutes. We found the leather construction and rubber sole make them practical, but our experience shows sizing can be inconsistent and the toe runs narrow for wider feet, so plan on trying them on if possible. Expect some initial stiffness that eases with wear; at a 6/10 they’re a solid, stylish option if you prioritize rain-ready versatility.

The Aimee Bootie offers water resistance and visual interest with wraparound straps and a functional buckle — during our review that detailing elevated rainy-day outfits while keeping feet protected. We found the leather and rubber sole combination feels substantial, but our experience shows the fit runs narrow even in wide sizes and the heel height can become uncomfortable after hours of standing. With a 6/10 score, these booties work well for shorter days and wet weather style, though comfort-seekers should test the fit and heel before buying.