Women, Boots, Knee-high or mid-calf
Shoes under $250
365 shoes under $250 from Ariat, Birkenstock, UGG and more. Most cost $155 to $229, and half cost less than $180.
Top brands: Ariat (49)Birkenstock (35)Clarks (13)Stuart Weitzman (13)
+Knee-high boot style covers the leg for cooler weather
+Available in knee-high or mid-calf height
+Women's boot in size 9.5 W for a wide width fit
−Tall shaft limits fit to certain calf measurements
$228.48-14%List: $265.00
as of 11/04/2026 00:21 PST - DetailsProduct details
Naturalizer Womens Kalina Knee High Tall Boots Wine 9.5 W
$228.48as of 11/04/2026 00:21 PST - Details
View on AmazonPros
+Knee-high boot style covers the leg for cooler weather
+Available in knee-high or mid-calf height
+Women's boot in size 9.5 W for a wide width fit
Cons−Tall shaft limits fit to certain calf measurements
How pros and cons are picked (About: Disclaimer)About this product
Men, Boots, Ankle or chukka
+Waterproof construction for wet weather
+Chukka ankle boot style
+Flexcraft design for added flexibility
$154.15-14%List: $180.00
as of 11/04/2026 15:41 PST - DetailsProduct details
Cole Haan Men's Newmark Grand Flexcraft Waterproof Chukka Boot, Black/Black Waterproof, 10.5-M US
$154.15as of 11/04/2026 15:41 PST - Details
View on AmazonPros
+Waterproof construction for wet weather
+Chukka ankle boot style
+Flexcraft design for added flexibility
+Men's boot in size 10.5 medium
Compared with the 365 shoes on this page+Waterproof: only 34 of 365 here have one
How pros and cons are picked (About: Disclaimer)About this product
Women, Boots, Western
+Tall 16-inch upper for full leg coverage
+Full-grain leather construction
+Western boot style for women
−Tall shaft may not suit shorter legs
$249.98-11%List: $279.95
as of 11/04/2026 11:44 PST - DetailsProduct details
ARIAT Women's Casanova X Toe Western Boot | Tall western boots with 16-inch upper, full-grain leather, and ATS
$249.98as of 11/04/2026 11:44 PST - Details
View on AmazonPros
+Tall 16-inch upper for full leg coverage
+Full-grain leather construction
+Western boot style for women
Cons−Tall shaft may not suit shorter legs
How pros and cons are picked (About: Disclaimer)About this product
+Made with leather upper material
$169.00-11%List: $189.00
as of 11/03/2026 23:10 PST - DetailsProduct details
About this product
Women, Boots
+Classic black boot for women
+Sized 10-10.5 in medium width
$229.95-8%List: $249.95
as of 11/04/2026 05:38 PST - DetailsProduct details
Taos Footwear Women's Crave Classic Black Boot 10-10.5 (M) US
$229.95as of 11/04/2026 05:38 PST - Details
View on AmazonPros
+Classic black boot for women
+Sized 10-10.5 in medium width
How pros and cons are picked (About: Disclaimer)About this product
Men, Boots, Western
$165.00-8%List: $179.95
as of 11/04/2026 11:43 PST - DetailsProduct details
ARIAT Men's Sport Rambler Western Boot, Aged Smokehouse, 9.5
$165.00as of 11/04/2026 11:43 PST - Details
View on AmazonAbout this product
Women
+Designed for women, in a size 9 medium fit
$187.99-6%List: $199.95
as of 11/03/2026 23:32 PST - DetailsProduct details
About this product
Men, Boots, Western
+Western boot style for riding and ranch wear
+Men's sizing for a classic cowboy fit
$195.56-5%List: $199.95
as of 11/04/2026 11:43 PST - DetailsProduct details
Pros
+Western boot style for riding and ranch wear
+Men's sizing for a classic cowboy fit
How pros and cons are picked (About: Disclaimer)About this product
Men, Boots, Work
+Water resistant upper
+Soft toe design
+6-inch boot height
−Uninsulated for cold conditions
$169.95
as of 11/03/2026 23:37 PST - DetailsProduct details
Irish Setter Ashby 6" Mens Soft Toe Work Boot, Brown, 11 M | Water Resistant, Uninsulated, D (Medium)
$169.95as of 11/03/2026 23:37 PST - Details
View on AmazonPros
+Water resistant upper
+Soft toe design
+6-inch boot height
+Medium width fit
Cons−Uninsulated for cold conditions
Compared with the 365 shoes on this page+Waterproof: only 34 of 365 here have one
How pros and cons are picked (About: Disclaimer)About this product
Men, Boots, Work
+Waterproof construction for wet conditions
+Slip and oil resistant outsole
+Six-inch shaft for added ankle coverage
−Soft toe offers less impact protection than steel toe
$154.99
as of 11/04/2026 14:37 PST - DetailsProduct details
BRUNT Marin (Soft Toe) - Men's Size 12, Black | 6" Waterproof Moc Toe Wedge Work Boot - EH Rated - Slip + Oil Resistant
$154.99as of 11/04/2026 14:37 PST - Details
View on AmazonPros
+Waterproof construction for wet conditions
+Slip and oil resistant outsole
+Six-inch shaft for added ankle coverage
+Soft toe for a lighter, more flexible toe box
Cons−Soft toe offers less impact protection than steel toe
Compared with the 365 shoes on this page+Waterproof: only 34 of 365 here have one
How pros and cons are picked (About: Disclaimer)About this product
Men, Boots, Work
+Waterproof construction keeps feet dry in wet conditions
+Insulated for cold-weather work
+Soft toe design with no metal in the toe box
−No safety toe protection for impact hazards
$174.95
as of 11/04/2026 05:40 PST - DetailsProduct details
Timberland PRO Men's Direct Attach 6 Inch Soft Toe Insulated Waterproof Industrial Work Boot, Wheat-2024 NEW, 10.5 M
$174.95as of 11/04/2026 05:40 PST - Details
View on AmazonPros
+Waterproof construction keeps feet dry in wet conditions
+Insulated for cold-weather work
+Soft toe design with no metal in the toe box
Cons−No safety toe protection for impact hazards
Compared with the 365 shoes on this page+Waterproof: only 34 of 365 here have one
How pros and cons are picked (About: Disclaimer)About this product
Men, Boots, Work
+Composite safety toe protects toes from impact and compression
+Waterproof construction keeps feet dry in wet conditions
+6 inch boot shaft for ankle coverage
−Composite toe is a less common choice for heavy metal impact
$179.95
as of 11/04/2026 05:40 PST - DetailsProduct details
Timberland PRO Men's TiTAN EV 6 Inch Composite Safety Toe Waterproof Industrial Work Boot, Teak Trailblazer Brown-2024
$179.95as of 11/04/2026 05:40 PST - Details
View on AmazonPros
+Composite safety toe protects toes from impact and compression
+Waterproof construction keeps feet dry in wet conditions
+6 inch boot shaft for ankle coverage
Cons−Composite toe is a less common choice for heavy metal impact
Compared with the 365 shoes on this page+Waterproof: only 34 of 365 here have one
How pros and cons are picked (About: Disclaimer)About this product
Men, Boat shoes
+Handsewn boat shoe construction from the Timberland Authentic line
+Lug sole designed for traction on wet decks
+Men's sizing in 11 M US
−Boat shoe style offers less ankle support than boots
$170.00
as of 11/04/2026 05:40 PST - DetailsProduct details
Timberland Men's Authentic 3-Eye Lug Handsewn Boat Shoe, Brown, 11 M US
$170.00as of 11/04/2026 05:40 PST - Details
View on AmazonPros
+Handsewn boat shoe construction from the Timberland Authentic line
+Lug sole designed for traction on wet decks
+Men's sizing in 11 M US
+Boat shoe style suited to casual and water wear
Cons−Boat shoe style offers less ankle support than boots
How pros and cons are picked (About: Disclaimer)About this product
Men, Boots, Work
+Steel safety toe protects toes from impact and compression
+Waterproof construction keeps feet dry in wet conditions
+Leather upper for durable everyday wear
−Steel toe adds weight compared with soft toe boots
$179.95
as of 11/04/2026 05:40 PST - DetailsProduct details
Timberland PRO Men's Direct Attach 6 Inch Steel Safety Toe Insulated Waterproof Industrial Work Boot, Wheat Nubuck, 13 M
$179.95as of 11/04/2026 05:40 PST - Details
View on AmazonPros
+Steel safety toe protects toes from impact and compression
+Waterproof construction keeps feet dry in wet conditions
+Leather upper for durable everyday wear
+6 inch boot shaft for ankle coverage
+Insulated for cold-weather work
Cons−Steel toe adds weight compared with soft toe boots
Compared with the 365 shoes on this page+Waterproof: only 34 of 365 here have one
How pros and cons are picked (About: Disclaimer)About this product
Men, Boots, Work
+Leather upper for durable wear
+Mid-top height offers more coverage than low work shoes
+Athletic traction outsole for footing on varied surfaces
−Soft toe offers no impact protection
$165.00
as of 11/03/2026 23:43 PST - DetailsProduct details
KEEN Utility Men's Gibson Hiker Mid Top Soft Toe Athletic Traction Durable Leather Work Boots, Belgian/Gum, 15 D
$165.00as of 11/03/2026 23:43 PST - Details
View on AmazonPros
+Leather upper for durable wear
+Mid-top height offers more coverage than low work shoes
+Athletic traction outsole for footing on varied surfaces
Cons−Soft toe offers no impact protection
How pros and cons are picked (About: Disclaimer)About this product
Men, Boots, Work
+Composite safety toe for impact protection on job sites
+Waterproof construction keeps feet dry in wet conditions
+Full-grain leather upper for durable wear
−Composite toe can make the boot heavier than soft toe styles
$169.95
as of 11/03/2026 23:43 PST - DetailsProduct details
KEEN Utility Men's Evanston 8" Composite Toe Waterproof Leather Durable Construction Work Boots, Bison/Black, 12 D
$169.95as of 11/03/2026 23:43 PST - Details
View on AmazonPros
+Composite safety toe for impact protection on job sites
+Waterproof construction keeps feet dry in wet conditions
+Full-grain leather upper for durable wear
+8-inch shaft adds ankle support
Cons−Composite toe can make the boot heavier than soft toe styles
Compared with the 365 shoes on this page+Waterproof: only 34 of 365 here have one
How pros and cons are picked (About: Disclaimer)About this product
Women, Loafers
+Made from leather for a durable upper
+Lug sole adds traction underfoot
+Croc print leather adds texture
−Lug sole adds bulk compared with a flat loafer
$160.00
as of 11/04/2026 15:41 PST - DetailsProduct details
Cole Haan Women's Treena Lug Loafer, Black Croc Print Leather, 7.5-C US
$160.00as of 11/04/2026 15:41 PST - Details
View on AmazonPros
+Made from leather for a durable upper
+Lug sole adds traction underfoot
+Croc print leather adds texture
Cons−Lug sole adds bulk compared with a flat loafer
How pros and cons are picked (About: Disclaimer)About this product
Women, Clogs and mules
+Narrow width fits narrow feet
+Suede upper with a leather material
+Wrapped clog design with a closed back
−Narrow width may not suit wider feet
$164.95
as of 11/04/2026 13:38 PST - DetailsProduct details
Birkenstock Womens Naples Wrapped Clog- Suede Midnight Women 11-11.5 Narrow
$164.95as of 11/04/2026 13:38 PST - Details
View on AmazonPros
+Narrow width fits narrow feet
+Suede upper with a leather material
+Wrapped clog design with a closed back
Cons−Narrow width may not suit wider feet
How pros and cons are picked (About: Disclaimer)About this product
Men, Oxfords and dress shoes
+Waterproof construction for wet conditions
+Calfskin leather upper
+Cap toe dress shoe style
−Calfskin upper shows scuffs more readily
$188.95
as of 11/03/2026 23:40 PST - DetailsProduct details
Johnston & Murphy Men's XC4 Branning Cap Toe Dress Shoe, Black Waterproof Calfskin, 9.5
$188.95as of 11/03/2026 23:40 PST - Details
View on AmazonPros
+Waterproof construction for wet conditions
+Calfskin leather upper
+Cap toe dress shoe style
Cons−Calfskin upper shows scuffs more readily
Compared with the 365 shoes on this page+Waterproof: only 34 of 365 here have one
How pros and cons are picked (About: Disclaimer)About this product
Men, Boots, Ankle or chukka
+Leather upper for a durable, classic boot
+Removable insole allows custom or replacement insoles
+Ankle or chukka boot style for everyday wear
−Leather upper needs regular conditioning to stay supported
$239.95
as of 11/04/2026 00:39 PST - DetailsProduct details
PIKOLINOS York Men’s Ankle Boots | Leather | Removable Insole | Black
$239.95as of 11/04/2026 00:39 PST - Details
View on AmazonPros
+Leather upper for a durable, classic boot
+Removable insole allows custom or replacement insoles
+Ankle or chukka boot style for everyday wear
Cons−Leather upper needs regular conditioning to stay supported
How pros and cons are picked (About: Disclaimer)About this product
Men, Boots
+Waterproof construction for wet conditions
+Full grain bomber leather upper
+Cap toe boot style
−Heavier build than a standard dress shoe
$228.95
as of 11/03/2026 23:40 PST - DetailsProduct details
Johnston & Murphy Men's XC+ Durham Cap Toe Boot, Dark Brown Waterproof Bomber Leather, 11.5 M
$228.95as of 11/03/2026 23:40 PST - Details
View on AmazonPros
+Waterproof construction for wet conditions
+Full grain bomber leather upper
+Cap toe boot style
Cons−Heavier build than a standard dress shoe
Compared with the 365 shoes on this page+Waterproof: only 34 of 365 here have one
How pros and cons are picked (About: Disclaimer)About this product
Men, Oxfords and dress shoes
+Full grain leather upper for durability
+Lace-up closure for a secure fit
+Cap toe dress shoe style
−Leather upper needs conditioning to hold shape
$178.95
as of 11/03/2026 23:40 PST - DetailsProduct details
Johnston & Murphy Men's Richland Cap Toe Lace-Up Dress Shoe, Tan Full Grain, 9.5
$178.95as of 11/03/2026 23:40 PST - Details
View on AmazonPros
+Full grain leather upper for durability
+Lace-up closure for a secure fit
+Cap toe dress shoe style
Cons−Leather upper needs conditioning to hold shape
How pros and cons are picked (About: Disclaimer)About this product
Women, Slippers
+Soft fur lining for warmth at home
+Genuine leather upper with slip-on design
+Fluffy fur styling suits casual indoor wear
−Backless slipper design offers limited support for outdoor walking
$239.99
as of 11/04/2026 00:19 PST - DetailsProduct details
Mules Shoes Women Real Fur Mules for Women Slip-on Fluffy Slippers with Soft Fur Lining, Genuine Leather Comfortable
$239.99as of 11/04/2026 00:19 PST - Details
View on AmazonPros
+Soft fur lining for warmth at home
+Genuine leather upper with slip-on design
+Fluffy fur styling suits casual indoor wear
Cons−Backless slipper design offers limited support for outdoor walking
How pros and cons are picked (About: Disclaimer)About this product
Men, Sandals and slides
+Suede leather upper for a soft, textured look
+Men's sandal with a closed-back Boston style
+Size 40 option in the N width
−Suede upper is less suited to wet conditions
$165.25
as of 11/04/2026 13:37 PST - DetailsProduct details
Birkenstock Men´s Boston Mocha Suede Sandals 40 N EU N 660463
$165.25as of 11/04/2026 13:37 PST - Details
View on AmazonPros
+Suede leather upper for a soft, textured look
+Men's sandal with a closed-back Boston style
+Size 40 option in the N width
Cons−Suede upper is less suited to wet conditions
How pros and cons are picked (About: Disclaimer)About this product
Women, Sandals and slides
+Oiled leather upper in black
+Genuine leather construction
+Listed in EU size 39 with US size conversions
−Leather upper needs more care than synthetic materials
$198.63
as of 11/04/2026 13:37 PST - DetailsProduct details
Birkenstock Women´s Boston Black Oiled Leather Sandals 39 EU (M6/L8 US) N 059463
$198.63as of 11/04/2026 13:37 PST - Details
View on AmazonPros
+Oiled leather upper in black
+Genuine leather construction
+Listed in EU size 39 with US size conversions
Cons−Leather upper needs more care than synthetic materials
How pros and cons are picked (About: Disclaimer)About this product
Unisex, Clogs and mules
+Clog and mule style with an enclosed heel for daily wear
+Unisex design suits a wide range of wearers
+Sized in UK measurements for a clear fit reference
−Clog style offers less support for long walks than sneakers
$155.00
as of 11/04/2026 13:37 PST - DetailsProduct details
Birkenstock Boston, Unisex Adults' Clogs, Brown,2.5 UK
$155.00as of 11/04/2026 13:37 PST - Details
View on AmazonPros
+Clog and mule style with an enclosed heel for daily wear
+Unisex design suits a wide range of wearers
+Sized in UK measurements for a clear fit reference
Cons−Clog style offers less support for long walks than sneakers
How pros and cons are picked (About: Disclaimer)About this product
Women, Clogs and mules
+Narrow width fits narrow feet
+Shearling lining for added warmth
+Chunky sole adds height
−Narrow width may not suit wider feet
$185.00
as of 11/04/2026 13:38 PST - DetailsProduct details
Birkenstock Womens Boston Chunky Shearling Clog Taupe 5-5.5 Narrow
$185.00as of 11/04/2026 13:38 PST - Details
View on AmazonPros
+Narrow width fits narrow feet
+Shearling lining for added warmth
+Chunky sole adds height
Cons−Narrow width may not suit wider feet
How pros and cons are picked (About: Disclaimer)About this product
Women, Flats
+Pointed toe flat shape for a sleek look
+Genuine leather upper material
+Women's sizing in size 9.5 medium
−Flat design offers no heel lift
$164.00
as of 11/04/2026 15:37 PST - DetailsProduct details
Chocolat Blu Women Shoes Abbe Pointy Toe Flat Shoe Brown Suede 9.5 M US
$164.00as of 11/04/2026 15:37 PST - Details
View on AmazonPros
+Pointed toe flat shape for a sleek look
+Genuine leather upper material
+Women's sizing in size 9.5 medium
Cons−Flat design offers no heel lift
How pros and cons are picked (About: Disclaimer)About this product
Compare specs
| pair of shoes | Gender | Type | Spec score | Price |
|---|---|---|---|---|
| Women | Boots | n/a | $228.48 as of 11/04/2026 00:21 PST - Details | |
| Men | Boots | n/a | $154.15 as of 11/04/2026 15:41 PST - Details | |
| Women | Boots | n/a | $249.98 as of 11/04/2026 11:44 PST - Details | |
| n/a | $169.00 as of 11/03/2026 23:10 PST - Details | |||
| Women | Boots | n/a | $229.95 as of 11/04/2026 05:38 PST - Details | |
| Men | Boots | n/a | $165.00 as of 11/04/2026 11:43 PST - Details | |
| Women | n/a | $187.99 as of 11/03/2026 23:32 PST - Details | ||
| Men | Boots | n/a | $195.56 as of 11/04/2026 11:43 PST - Details | |
| Men | Boots | n/a | $169.95 as of 11/03/2026 23:37 PST - Details | |
| Men | Boots | n/a | $154.99 as of 11/04/2026 14:37 PST - Details |



























