Men's Shoes › To Boot New York › chukka boots

Burkett Cap Toe Boot

Men's To Boot New York Burkett Cap Toe Boot - Brown - Casual boots Polished calfskin leather adds sophisticated shine to a classic Italian boot with a smart arch-support insole and flexible rubber sole. Lace-up style Removable, cushioned insole with... more

Shawn Chelsea Boot

Men's To Boot New York Shawn Chelsea Boot - Brown - Casual boots Classic Chelsea style defines this handsome suede ankle boot furnished with an arch-supporting cushioned footbed for superior comfort. Pull-on style with elastic gore insets Cushioned... more

Driving Shoe - Blue - To Boot New York Slip-Ons

Men's To Boot New York Driving Shoe - Blue - Loafers Bold contrast stitching defines a charming Italian driving shoe fitted with cushioned arch support for comfort that lasts. Slip-on style Suede upper/leather lining/rubber sole Made in Italy Men's Shoes. more

Deville Leather Penny Loafer - Black - To Boot New York Slip-Ons

Men's To Boot New York Deville Leather Penny Loafer - Black - Loafers Pebbled or sleek Italian leather creates a high-quality, classy penny loafer. Apron toe Leather upper and lining, manmade sole Made in Italy. more

Largo Chelsea Boot

Men's To Boot New York Largo Chelsea Boot - Brown - Casual boots Supple calfskin elevates a handsome Italian Chelsea boot with an arch-support footbed for all-day comfort. Pull-on style with elastic gore insets Leather upper and lining/rubber sole Made... more

Bedell Chelsea Boot

Men's To Boot New York Bedell Chelsea Boot - Brown - Casual boots A handmade sole with hammered brass nails grounds a rustic Italian boot with a smart arch-support footbed. Pull-on style with elastic gore insets Leather upper, lining and sole Made in... more

Shelby Ii Chelsea Boot

Men's To Boot New York Shelby Ii Chelsea Boot - Brown - Casual boots A flexible combination sole adds rugged grounding to this Italian-made Chelsea boot crafted from sleek calfskin leather with a cushy, arch-supporting footbed. Cushioned footbed with... more

Largo Chelsea Boot

Men's To Boot New York Largo Chelsea Boot - Brown - Casual boots Supple calfskin elevates a handsome Italian Chelsea boot with an arch-support footbed for all-day comfort. Pull-on style with elastic gore insets Leather upper and lining/rubber sole Made... more

Belvedere Zip Boot

Men's To Boot New York Belvedere Zip Boot - Brown - Casual boots Burnished calfskin leather elevates a stylish Italian boot fitted with a smart side zipper and comfortable arch support. Side zip closure Arch support Leather upper, lining and sole Made... more

Largo Chelsea Boot

Men's To Boot New York Largo Chelsea Boot - Black - Casual boots Supple calfskin elevates a handsome Italian Chelsea boot with an arch-support footbed for all-day comfort. Pull-on style with elastic gore insets Leather upper and lining/rubber sole Made... more

Muller Boot

Men's To Boot New York Muller Boot - Brown - Casual boots Tonal stitching and a burnished upper add modern sophistication to an Italian-made boot grounded by a durable lug sole. Side zip closure Leather upper and lining/leather and rubber sole Made in... more

Belvedere Zip Boot

Men's To Boot New York Belvedere Zip Boot - Brown - Casual boots Burnished calfskin leather elevates a stylish Italian boot fitted with a smart side zipper and comfortable arch support. Side zip closure Arch support Leather upper, lining and sole Made... more

Burkett Cap Toe Boot

Men's To Boot New York Burkett Cap Toe Boot - Black - Casual boots Polished calfskin leather adds sophisticated shine to a classic Italian boot with a smart arch-support insole and flexible rubber sole. Lace-up style Removable, cushioned insole with... more

Addison Double Monk Strap Shoe

Men's To Boot New York Addison Double Monk Strap Shoe - Blue - Monk shoes All-leather construction means sophisticated styling in this suede shoe designed with dual monk straps and comfortable arch support. Adjustable two-buckle monk strap Removable,... more

Cassidy Moc Toe Loafer

Men's To Boot New York Cassidy Moc Toe Loafer - Brown - Loafers Step into breathable comfort with this flexible moc-toe loafer with a supple leather lining and arch support. Removable insole with arch support Leather upper and lining/rubber sole Made... more

Dickerson Penny Loafer

Men's To Boot New York Dickerson Penny Loafer - Black - Loafers A classic penny keeper and sleek leather construction lend timeless sophistication to a polished loafer perfect for any occasion. Leather upper and lining/leather and rubber sole Made in... more

Colton Sneaker

Men's To Boot New York Colton Sneaker - Blue - Low-top sneakers Buttery-soft, burnished napa leather brings a refined look to this street-smart Italian sneaker with a flexible rubber sole. Lace-up style Removable insole Leather upper and lining/rubber... more

Barbera Sneaker

Men's To Boot New York Barbera Sneaker - Brown - Low-top sneakers Full-grain tumbled leather handcrafted in Italy defines the look of this casual-cool sneaker cushioned with arch support. Lace-up style Removable, cushioned insole with arch support... more

Derrick Sneaker

Men's To Boot New York Derrick Sneaker - Blue - Low-top sneakers Burnished suede lends vintage charm to a dapper lace-up sneaker resting on a cushioned insole and grippy rubber cupsole. Removable, cushioned insole with arch support Leather upper and... more

Troye Loafer

Men's To Boot New York Troye Loafer - Blue - Loafers Ultrasoft Italian suede gives a luxe look and feel to this casual-cool loafer set atop a sneaker sole. Removable, cushioned insole with arch support Leather upper and lining/rubber sole Made in Italy. more

Sierra Lace-up Sneaker

Men's To Boot New York Sierra Lace-up Sneaker - Black - Low-top sneakers Italian calfskin leather brings a refined look to a street-smart sneaker furnished with an arch-supporting, cushioned insole for superior comfort. Removable, cushioned insole with... more

Dickerson Penny Loafer

Men's To Boot New York Dickerson Penny Loafer - Black - Loafers A classic penny keeper and sleek leather construction lend timeless sophistication to a polished loafer perfect for any occasion. Leather upper and lining/leather and rubber sole Made in... more

Declan Plain Toe Derby

Men's To Boot New York Declan Plain Toe Derby - Black - Derbies Finely textured calfskin leather defines a flexible Italian derby featuring an arch-support footbed for superior comfort. Lace-up style Leather upper, lining and sole Made in Italy. more

Bolla Sneaker

Men's To Boot New York Bolla Sneaker - White - Low-top sneakers Clean, contemporary style meets optimal comfort in this pebbled-leather sneaker set on a lightweight rubber sole. Pull-on style with elastic laces Removable, cushioned insole with arch... more

Tesoro Penny Loafer

Men's To Boot New York Tesoro Penny Loafer - Brown - Loafers Streamlined design showcases the rich leather of a timeless penny loafer built with cushioned arch support and a flexible sole for superior comfort. Cushioned insole with arch support Leather... more

Tesoro Penny Loafer

Men's To Boot New York Tesoro Penny Loafer - Brown - Loafers Streamlined design showcases the rich leather of a timeless penny loafer built with cushioned arch support and a flexible sole for superior comfort. Cushioned insole with arch support Leather... more

Perry Venetian Loafer

Men's To Boot New York Perry Venetian Loafer - Black - Loafers A fine grosgrain overlay tops a stylish Italian loafer fashioned from calfskin patent leather. Leather and textile upper/leather lining and sole Made in Italy Men's Shoes. more

Pacer Sneaker

Men's To Boot New York Pacer Sneaker - Blue - Low-top sneakers Smart suede construction defines a charming Italian sneaker with cushioned arch support for all-day comfort. Lace-up style Removable insole Leather upper and lining/rubber sole Made in... more

Palo Alto Driving Shoe

Men's To Boot New York Palo Alto Driving Shoe - Brown - Loafers Premium leather construction elevates a casually charming driving shoe featuring cushioned arch support. Leather upper and lining/rubber sole Made in Italy Men's Shoes. more

Amedeo Derby

Men's To Boot New York Amedeo Derby - Brown - Derbies Burnished leather and a plain toe lend modern sophistication to an Italian leather derby outfitted with a cushioned footbed for lasting comfort. Cushioned footbed with arch support Leather upper and... more

Jett Derby

Men's To Boot New York Jett Derby - Brown - Derbies A supple suede upper and streamlined silhouette distinguish a sophisticated derby grounded by a durable rubber cupsole for modern appeal. Lace-up style Cushioned footbed with arch support Leather... more

Solaro Sneaker

Men's To Boot New York Solaro Sneaker - White - Low-top sneakers Add a luxe element to your everyday style with a smooth suede sneaker grounded by a cushioned, arch-supporting insole. Lace-up style Removable, cushioned insole with arch support Leather... more

Beamon Loafer

Men's To Boot New York Beamon Loafer - Brown - Loafers Stylish piping outlines a flexible and supple Italian loafer set atop a plush insole with comfortable arch support. Removable, cushioned insole with arch support Leather upper, lining and sole Made... more

Cassidy Moc Toe Loafer

Men's To Boot New York Cassidy Moc Toe Loafer - Blue - Loafers Step into breathable comfort with this flexible moc-toe loafer with a supple leather lining and arch support. Removable insole with arch support Leather upper and lining/rubber sole Made in... more

Hammill Cap Toe Double Monk Strap Shoe

Men's To Boot New York Hammill Cap Toe Double Monk Strap Shoe - Brown - Monk shoes A double monk strap and smart cap toe lend sophisticated charm to a rich leather shoe grounded by a cushioned footbed for lasting comfort. Cushioned footbed with arch... more

Stone Slip-on Sneaker

Men's To Boot New York Stone Slip-on Sneaker - Black - Low-top sneakers Creamy suede construction defines a versatile Italian slip-on with an arch-support footbed. Leather upper and lining/rubber sole Made in Italy. more

Nico Oxford

Men's To Boot New York Nico Oxford - Brown - Oxfords A sueded inside heel and flexible outsole elevate the comfort of a polished leather oxford cushioned by an arch-supporting insole. Lace-up style Cushioned insole with arch support Removable insole... more

Ainsworth Sneaker

Men's To Boot New York Ainsworth Sneaker - Brown - Low-top sneakers Debossed logo lettering on the tongue elevates this napa leather sneaker cushioned by plush arch support. Removable, cushioned insole with arch support Leather upper and lining/rubber... more