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

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

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

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

Aalborg Plain Toe Derby - Black - To Boot New York Lace-Ups

Men's To Boot New York Aalborg Plain Toe Derby - Black - Derbies Bright patent leather elevates a charming Italian derby with formal appeal. Smart arch support ensures exceptional comfort. Lace-up closure Leather upper, lining and sole Made in Italy... 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

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

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

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

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

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

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

Ravello Penny Loafer - Brown - To Boot New York Slip-Ons

Men's To Boot New York Ravello Penny Loafer - Brown - Loafers A classic penny keeper and moc toe lend sophisticated charm to a burnished leather loafer that will complement your work-to-weekend style. Cushioned footbed with arch support Leather upper,... 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

Aalborg Plain Toe Derby

Men's To Boot New York Aalborg Plain Toe Derby - Black - Derbies Bright patent leather elevates a charming Italian derby with formal appeal. Smart arch support ensures exceptional comfort. Lace-up closure Leather upper, lining and sole Made in Italy... 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

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

Chambers Apron Toe Suede Loafer

Men's To Boot New York Chambers Apron Toe Suede Loafer - Blue - Loafers A deconstructed penny strap and squared apron toe distinguish a loafer made of Italian suede with a rubber sole to smartly ground any favorite look. Cushioned insole Leather upper... 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

Chambers Apron Toe Suede Loafer

Men's To Boot New York Chambers Apron Toe Suede Loafer - Brown - Loafers A deconstructed penny strap and squared apron toe distinguish a loafer made of Italian suede with a rubber sole to smartly ground any favorite look. Cushioned insole Leather upper... more

Magnus Driving Shoe

Men's To Boot New York Magnus Driving Shoe - Brown - Loafers Woven calfskin leather adds rich texture to a classic Italian driving shoe with smart arch support. Leather upper and lining/rubber sole Made in Italy. 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

Zenith Penny Loafer

Men's To Boot New York Zenith Penny Loafer - Brown - Loafers A woven upper and classic penny keeper create modern dimension on an Italian leather loafer grounded by a cushioned footbed for comfortable wear. Cushioned footbed with arch support Leather... more

Carlin Sneaker

Men's To Boot New York Carlin Sneaker - White - Low-top sneakers A touch of rich color elevates a stylish Italian sneaker crafted from supple leather with smart arch support. Lace-up closure Removable insole 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 - Black - 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

Pescara Sneaker

Men's To Boot New York Pescara Sneaker - Brown - Low-top sneakers A burnished leather upper adds modern sophistication to a low-profile sneaker grounded by a cushioned insole and classic cupsole for street-savvy appeal. Removable, cushioned insole with... more

Bower Monk Strap Shoe

Men's To Boot New York Bower Monk Strap Shoe - Brown - Monk shoes Supple Italian suede lends undeniable style to a handsome monk-strap shoe cushioned by a plush insole with arch support. more

Stone Slip-on Sneaker

Men's To Boot New York Stone Slip-on Sneaker - Brown - 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

Key Largo Driving Shoe

Men's To Boot New York Key Largo Driving Shoe - Black - Loafers Richly textured deerskin leather elevates a handsome Italian driving shoe with an arch-support footbed for exceptional ease. Leather upper and lining/rubber sole Made in Italy Men's Shoes. more

Chance Derby

Men's To Boot New York Chance Derby - Black - Derbies A glossy leather upper lends timeless sophistication to a luxe derby that will complement your polished looks. Lace-up style Leather upper and lining/synthetic sole Made in Italy. more

Ravello Penny Loafer

Men's To Boot New York Ravello Penny Loafer - Black - Loafers A classic penny keeper and moc toe lend sophisticated charm to a burnished leather loafer that will complement your work-to-weekend style. Cushioned footbed with arch support Leather upper,... 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

Troye Loafer

Men's To Boot New York Troye Loafer - Brown - 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

Thorpe Leather Loafer

Men's To Boot New York Thorpe Leather Loafer - Brown - Loafers A sleek, minimalist silhouette lends sophisticated style to an Italian loafer fashioned from soft calfskin leather. Removable insole Leather upper, lining and 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

Vieques Driving Shoe

Men's To Boot New York Vieques Driving Shoe - Brown - Loafers Richly textured deerskin leather elevates a smart Italian driving shoe with a comfortable arch-support footbed. Removable insole Leather upper and lining/rubber sole Made in Italy Men's Shoes. more

Jaydon Penny Driving Loafer

Men's To Boot New York Jaydon Penny Driving Loafer - Gray - Loafers A classic penny keeper and moc toe add timeless appeal to a leather loafer grounded by a cushioned footbed and segmented driver sole that wraps up the heel. Cushioned footbed with arch... more