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

Zero drop, wide toe box boots with heels, and barefoot options

Lems Waterproof Boulder Boots

(Last updated 1/27/2026. This list does not contain any affiliate links.)

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:
Boots with elevated heels | Barefoot boots

Zero drop boots with cushion:

Conker (select one of the flat sole options, $):

• Chelsea

• Cowboy

• Derby

Dolfie Paradise:

• Eddie boots (Moccasin)

El Naturalista:

• Nomada Chelsea boots (faux heel)

• Nomada Derby boots (faux heel; read my review here)

• Tribu models

Free Form (elongated toe box; zero drop or elevated heel options, $$):

• Limited stock

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; read my review here)

• Via Andante (lace-up)

• Wind (knee-high, zipper)

Jim Green (custom options available):

• Barefoot African Ranger boots (lace-up; x-wide version)

• Barefoot African Trooper boots (Derby)

• Barefoot Meander (Moc Toe; pre-order)

• Barefoot Stockman boots (Chelsea)

• Barefoot Workhorse (Moc Toe; pre-order)

Lems:

• Women’s boot collection

• Men’s boot collection

Nicks Boots ($$; Kletterlift and Sierra soling options are zero drop):

• Ridgeline (Derby)

• Strider (Derby; read my overview here)

Boots with an anatomical toe box and elevated heels:

Angulus:

• Wide Fit boots

BÄR:

• Women’s boot collection

• Men’s boot collection

Birkenstock:

• Birmingham Lace (Derby)

• Birmingham Slip On (Chelsea)

• Highwood Lace (Derby)

• Highwood Slip On (Chelsea)

• Prescott (Derby)

Børn:

• Analia (Moccasin)

• Brody (Chelsea)

• Tula (zipper)

Clarks:

• Wallabee boots (Moccasin)

Corcoran:

• Jump Boots (Derby, Munson-style last)

Crush on Retro:

• Broad Toe Balmoral

El Naturalista:

• Arenisca

Duckfeet ($):

• Boot collection

Grünbein:

• Naturschuh/Natural fit models

Harlem Shoes (dance shoes; choose rubber sole for outdoor wear):

• Barefoot Derby boots

• Barefoot Smooth boots (Oxford)

Helvesko ($):

• Allen (Chelsea)

• Birgitta (knee-high)

• Carter (Chelsea)

• Elvin (Chukka)

• 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)

Hotter:

• Ballinderry (zipper, mid-calf)

• Derrymore II (zipper, mid-calf)

• Murmur (zipper)

• Rumour (zipper)

• Whisper (zipper)

Iron Boots (MTO/GMTO, $$$):

• 5515 (Derby)

• The Great Escape/Emily (Derby)

Keen:

• KNX Chukka

• San Jose Soft Toe Chelsea

• San Jose Soft Toe (Derby)

L’Artiste:

• Chesapeake boots (zipper, ankle)

Laia Zapateiros:

• Pato Chelsea

• Pato Chukka

LL Bean:

• Stonington boots (moc toe)

• Upland Hunter’s boot (moc toe)

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)

Revere:

• Aberdeen Boot (zipper, ankle)

• Charleston Boot (zipper, ankle)

• Salzburg Bootie (zipper, ankle)

Stegmann:

• Amalia (zipper, ankle)

• Baden (Moccasin)

• Lieben (Chelsea, ankle)

Trippen ($$):

• Men’s boot collection

• Women’s boot collection

Vibae:

• Short boots

• Woodstock (mid-calf)

Zardus:

• Almeida

• Gomes (moc toe)

• Sousa (Chukka)

Barefoot boots (flat, thin soles):

Angles Fashion:

• Nyx (Chelsea)

• Orpheus (Derby)

BÄR:

• Jaden (Chukka)

• Jody (Chelsea)

• Lynn 2.0 (zipper, knee high)

Beflamboyant:

• Chelsea boots

• Combat boots

• Cowboy boots

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)

• Fiona (Western)

• Flora (Derby, mid-calf)

• Florence (Derby)

Ohne Project:

• Zuri (Chelsea)

Peerko:

• Go (Derby)

Proalp:

• Barefoot boot collection

Sambas the Bambas:

• Leo Amarillo (Derby)

Shapen:

• Boot collection

Zaqq:

• Women’s boots

• Men’s boots