To Boot Men's Casual Shoes on Sale

Showing 25 Men's Casual Shoes filtered to 1 brand and 1 discount

Free Shipping $100+

To Boot Thorne Penny Loafer
To Boot Thorne Penny Loafer 

Details Sizing: True to size. Leather upper, manmade sole Round moc toe Penny slot strap Slip-on Cushioned insole Made in Italy

Get Sale Alert

Free Shipping: FREESHIP

To Boot Clifton Suede Penny Loafers
To Boot Clifton Suede Penny Loafers 

A pair of timeless penny loafers lend a dapper look. Moc toe. Suede leather upper. Penny slider details. Slip-on style. Leather lining. Rubber sole. Leather insole. Made in Italy.

Get Sale Alert

Free Shipping $100+

To Boot Oscar Slip-On Sneaker
To Boot Oscar Slip-On Sneaker 

Details Sizing: True to size. Suede or leather upper, rubber sole Round toe Topstitched bumper Perforated vamp Dual gored vamp insets Slip-on Lightly padded footbed Grip sole Made in Italy

Get Sale Alert

Free Shipping $100+

To Boot Ringer Slip-On Sneaker
To Boot Ringer Slip-On Sneaker 

Suede upper, manmade sole Round toe Suede construction Dual elastic side panels Slip-on Cushioned insole and cuff Made in Italy

Get Sale Alert

Free Ship $99+: SHIP99

To Boot Pieter Leather Loafers
To Boot Pieter Leather Loafers 

Polished loafers crafted from Italian leather Block heel, 1" leather upper Slip-on style Leather lining and sole Made in Italy

Get Sale Alert

Free Shipping $99+: SHIP99

To Boot Men's Charles Leather Slip-On Shoes
To Boot Men's Charles Leather Slip-On Shoes 

Square toe slip-on shoes crafted from leather Leather upper Slip-on style Leather lining Synthetic sole Made in Italy

Get Sale Alert

Free Shipping $99+: SHIP99

To Boot Men's Forest Leather Penny Loafers
To Boot Men's Forest Leather Penny Loafers 

Smart leather loafers cut from polished leather Heel, 1" Leather upper Slip-on style Leather lining Synthetic sole Made in Italy

Get Sale Alert

Free Shipping $99+: SHIP99

To Boot Men's Slip-On Leather Sneakers
To Boot Men's Slip-On Leather Sneakers 

Slip-on sneakers in smooth leather Leather upper Platform, 1.25" (30mm) Leather and textile lining Man-made sole Made in Italy

Get Sale Alert

Free Ship $99+: SHIP99

To Boot Charles Leather Slip-On Shoes
To Boot Charles Leather Slip-On Shoes 

Square toe slip-on shoes crafted from leather Leather upper Slip-on style Leather lining Synthetic sole Made in Italy

Get Sale Alert

Free Ship $99+: SHIP99

To Boot Turin Leather Penny Drivers
To Boot Turin Leather Penny Drivers 

Versatile penny drivers crafted from smooth leather Leather upper Square toe Slip-on style Leather lining Man-made sole Made in Italy

Get Sale Alert

Free Ship + Free Returns

To Boot Alek Penny Loafer
To Boot Alek Penny Loafer 

A classic penny strap bridges an Italian-made loafer crafted from soft polished leather with a squared toe and a slightly exaggerated profile. Style Name:To Boot New York Alek Penny Loafer (Men). Style Number: 5255317_4. Available in stores.

Get Sale Alert

$25 Off $100: PRIVATE

To Boot Colman Slip-On Sneakers
To Boot Colman Slip-On Sneakers 

Fits true to size, order your normal size Elastic goring at sides and across instep for a flexible fit Slip on Logo at heel Nubuck leather upper, leather lining, rubber sole Made in Italy

Get Sale Alert

$25 Off $100: PRIVATE

To Boot Stewart Perforated Slip On Sneakers
To Boot Stewart Perforated Slip On Sneakers 

Fits true to size, order your normal size Elastic goring at sides for a flexible fit Slip on Padded ankle Suede upper, leather lining, rubber sole Made in Italy

Get Sale Alert

$25 Off $100: PRIVATE

To Boot Lloyd Suede Drivers
To Boot Lloyd Suede Drivers 

Crafted in rich blue Italian suede, the Lloyd driver blends comfort and style for an anytime look that's easy to dress up and down. Moc toe with contrast topstitching Lace detail at the tongue Leather/rubber Hand wash Made in Italy

Get Sale Alert

$25 Off $100: PRIVATE

To Boot Men's Cliff Leather Slip-On Sneakers
To Boot Men's Cliff Leather Slip-On Sneakers 

Fits true to size, order your normal size Crisscross elastic straps at vamp for a flexible fit Pebbled leather detailing Logo at heel Leather upper, leather lining, rubber sole Made in Italy

Get Sale Alert

Free Ship $99+: SHIP99

To Boot Slip-On Leather Sneakers
To Boot Slip-On Leather Sneakers 

Slip-on sneakers in smooth leather Leather upper Platform, 1.25" (30mm) Leather and textile lining Man-made sole Made in Italy

Get Sale Alert

Free Ship $99+: SHIP99

To Boot Contrast Suede Drivers
To Boot Contrast Suede Drivers 

Contrast stitching accents this soft, suede driver style for the ultimate in contemporary appeal. Suede upper Leather lining Rubber sole Padded insole Made in Italy

Get Sale Alert

Free Ship $99+: SHIP99

To Boot Forest Leather Penny Loafers
To Boot Forest Leather Penny Loafers 

Smart leather loafers cut from polished leather Heel, 1" Leather upper Slip-on style Leather lining Synthetic sole Made in Italy

Get Sale Alert

To Boot Men's Grant Oxford
To Boot Men's Grant Oxford 

Double buckle monk strap

Get Sale Alert

Free Ship + Free Returns

To Boot Glendale Penny Driver
To Boot Glendale Penny Driver 

A classic penny strap bridges a squared-toe loafer cut from richly pebbled leather and set on a segmented driving sole that wraps neatly up the heel. Style Name:To Boot New York Glendale Penny Driver (Men). Style Number: 5355305. Available in stores.

Get Sale Alert

Free Ship + Free Returns

To Boot Norse Penny Loafer with Genuine Shearling
To Boot Norse Penny Loafer with Genuine Shearling 

Plush genuine shearling lining provides a refined and comfortable update for a timeless penny loafer. Style Name:To Boot New York Norse Penny Loafer With Genuine Shearling (Men). Style Number: 5385951. Available in stores.

Get Sale Alert

To Boot Men's Harper Penny Loafer
To Boot Men's Harper Penny Loafer 

Penney drivers

Get Sale Alert

Free Shipping any 2+ items

To Boot Barton
To Boot Barton 

Cool- casual and versatile- the Barton sneaker is the ideal go-to sneaker for any outfit. ; Smooth- genuine leather upper. ; Flat lace-up construction. ; Topstitching detail. ; Padded tongue and collar. ; Leather sock lining and padded leather insole. ; Durable rubber midsole and sole. ; Made in Italy. Measurements: ; Weight: 1 lb 3 oz ; Product measurements were taken using size 11.5- width M. Please note that measurements may vary by size. ; Weight of footwear is based on a single item- not a pair.

Get Sale Alert

Free Shipping any 2+ items

To Boot Franklin
To Boot Franklin 

Create a refined look with the To Boot New York Franklin chukka. ; Textured leather upper features a burnished finish. ; Lace-up front. ; Rounded toe. ; Leather lining and insole. ; Flexible synthetic sole. ; Made in Italy. Measurements: ; Weight: 1 lb 6 oz ; Shaft: 4 in ; Product measurements were taken using size 11- width M. Please note that measurements may vary by size. ; Weight of footwear is based on a single item- not a pair.

Get Sale Alert

Free 3-day Shipping + FR

To Boot Baldwin Suede Shoes with Monk Strap & Crepe Sole
To Boot Baldwin Suede Shoes with Monk Strap & Crepe Sole 

Leather: Calfskin Single-strap style Buckle at side Rubber sole Dust bag included Made in Italy This item cannot be gift-boxed

Get Sale Alert
Top