A list of boots for Fall that won't squish your toes

Boots with wide and/or anatomical toe boxes

Lems Waterproof Boulder Boots

(Last updated 1/16/2025)

With Autumn swiftly approaching, here’s a list of boots to aid you in your search for footwear that won’t squish your toes—whether you want something in a barefoot-style with thin soles, zero drop with cushion, or boots with elevated heels.

You may think the toe boxes on some of these boots look too narrow for you, and you might be right. Since not everyone has wide feet I’ve included some brands that make footwear with anatomically shaped toe boxes that would be best suited for those with average width feet.

Generally speaking, you’ll usually find the widest toe boxes on the barefoot brands, while the boots with elevated heels tend to be on the narrower end of the spectrum. There are several comprehensive lists of barefoot boots out there already so I’ve been very selective with the ones I put on the list.

(Jump to zero drop boots with cushion or boots with elevated heels)

Barefoot (flat, thin soles):

birchbury_apparel

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Angles Fashion:

• Nyx (Chelsea)

• Orpheus (Derby)

BÄR:

• Jaden (Chukka)

• Jamira (Chelsea, knee high)

• Jody (Chelsea)

• Lynn 2.0 (zipper, knee high)

Blusun:

• Boot models

Birchbury:

• Carnforth (Chukka)

Camper:

• Women’s boot collection

Carets:

• Ares (Derby, faux heel & elongated toe box)

Feelgrounds:

• Chelsea

• Patrol Lite (lace-up)

Groundies:

• Women’s boot collection

• Men’s boot collection

Jancarik:

• Mark (Derby)

• Buckle (Jodhpur)

Koel:

• Fea (Chukka)

• Fila (Chelsea)

• Fiona (Western)

• Flora (Derby, mid-calf)

• Florence (Derby)

Peerko:

• Go (Derby)

Proalp:

• Barefoot boot collection

Sambas the Bambas:

• Leo Amarillo (Derby)

Shapen:

• Boot collection

Zaqq:

• Women’s boots

• Men’s boots

Zero drop (flat soles with cushion):

gea_waldviertler_offiziell

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Conker (be sure to select one of the flat sole options):

• Chelsea

• Cowboy

• Derby

Free Form:

• Made to Order boots (elongated toe box; zero drop or elevated heel options)

GEA Waldviertler (remove insole to make them flat):

• Bronca/Bronco (zipper; wool lined)

• Filzi (zipper, mid-calf)

• Flexwind (Chukka; wool lined)

• Jaga Flex (Derby)

• Mustang (Chelsea)

• Via Andante (lace-up)

• Wind (knee-high, zipper)

Jim Green:

• Barefoot African Ranger boots (lace-up)

• Barefoot African Trooper boots (Derby)

• Barefoot Stockman boots (Chelsea)

Lems:

• Women’s boot collection

• Men’s boot collection

Anatomical toe box and elevated heels:

ironboots_usa

A post shared by @ironboots_usa

BÄR:

• Women’s boot collection

• Men’s boot collection

Birkenstock:

• Bryson (Derby)

• Highwood Lace (Derby)

• Highwood Slip On (Chelsea)

• Prescott (Derby)

• Stalon (Chelsea)

Børn:

• Analia (Moccasin)

• Brock (Moccasin)

• Brody (Chelsea)

• Tula (zipper)

Chaco:

• Paonia boot line

Clarks:

• Wallabee boots (Moccasin)

Corcoran:

• Jump Boots (Derby, Munson-style last)

Dr. Sole:

• OZ Trooper Service Boot (Derby, Munson-style last)

Duckfeet:

• Boot collection

Fairysteps (made by hand with limited availability):

• In stock options

Grünbein:

• Naturschuh/Natural fit models

Gudrun Sjödén:

• Nappa boots (Derby)

Harlem Shoes:

• Barefoot Smooth boots (Oxford, dance shoes; choose rubber sole for outdoor wear)

Helvesko:

• Allen (Chelsea)

• Birgitta (knee-high)

• Hazel (Chelsea)

• Janelle (Derby)

• Jella (Chelsea, wingtip)

• Melvin (Chukka)

• Padua (zipper, fringe)

• Pavia (buckle, zipper)

• Romana (zipper, slouch)

• Santina (Chelsea, buckle)

Hey Dude:

• Bradley (Moccasin)

• Wally Mid (Moccasin)

• Wendy Mid (Moccasin)

Hotter:

• Ballinderry (zipper, mid-calf)

• Derrymore II (zipper, mid-calf)

• Ellery (Derby)

• Murmur (zipper)

• Rumour (zipper)

• Whisper (zipper)

Iron Boots:

• The Great Escape (Derby)

Keen:

• KNX Chukka

• San Jose Soft Toe (Derby)

Loewe ($$$):

• Campo Chelsea boot

• Campo Biker boot (pull-on)

• Campo Biker high boot (pull-on)

• Campo ankle boot (Derby)

• Sierra combat boot

Loints of Holland:

• Boot collection

Naot:

• Manga (lace-up)

• Patu (lace-up)

• Wanaka (zipper, ankle)

Nature:

• Anton (Moccasin)

• Women’s boot collection

Nick’s Boots:

• MTO boots on Thurman last (Derby, Munson-style last)

Proalp:

• Sporty Elegant boot collection

Quoddy:

• Mt. Desert Boot (Chukka/moccasin)

Stegmann:

• Baden (Moccasin)

• Lieben (Chelsea, ankle)

Trippen:

• Men’s boot collection

• Women’s boot collection

Vibae:

• Boot collection