Men’s
Shoes & Boots

From shearling-lined clogs and leather sandals to waterproof sneakers and cowboy boots, we have a diverse selection of men’s shoes & boots. With styles exclusive to Territory Ahead and carefully curated name-brand selections, our men’s shoes and boots are inspired by the journey. Many styles are available in men’s sizes 7.5-13.

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Item 190648
Price $499.00

Austin Cowboy Boots from Lucchese®: From Lucchese's Heritage Collection, made in Texas since 1883. A subtle yet highly intricate pattern on the quarter contains three subtle thread colors that add just the right amount of dimension to this rugged, comanche roughout suede boot. The burnished toe and heel create a casual, worn-in look for a laid-back style. Lucchese boots feature traditional leather soles, which are flexible and breathable. Lemonwood pegs complete the structure of the boot by holding the insole and outsole together, maintaining the integrity of the hand-lasted instep fit. Flex lite sole feature rubber inlays under the instep for added comfort and traction. Standard rounded toe. 1.75" stacked leather heel with durable rubber heel tip. Made in Texas.

Item 190292
Price $120.00

Coburn Waterproof Low Hikers From Ahnu®: A shoe version of Ahnu's Coburn Lace-Up Boots with waterproof leather uppers and rubber soles. Numentum® Hike technology centers and guides the foot to promote balance. Double-density compression-molded ethylene vinyl acetate with medial and lateral postings for underfoot comfort and stability. Integrated thermoplastic polyurethane shank and arch support for torsional rigidity and mid-foot support. Imported.

NOTE: This item is excluded from promotional discounts.

Item 190519
Price $375.00

Clayton Leather Cowboy Boots from Lucchese®: Lucchese Bootmakers have been creating iconic handmade boots since 1883. If cowboy boots were eligible for Lifetime Achievement Awards, these would win, feet down. The distressed, tumbled leather gets better the more you wear them, and the John Wayne toes and hand-laced braiding at the sides and pull straps give them major swagger. Leather linings and fully padded footbeds provide legendary comfort. Goodyear welt construction. 12" shaft height; 1 5/8" heels. Handmade in Mexico.

Item 190565
Price $175.00
Blundstone 550 Water Resistant Boots from Blundstone®: Versatile and comfortable with water-resistant leather or oiled nubuck uppers, leather lining, and removable footbed. They're just the right weight with just the right look, and they get better with age. Side gores and double pull straps make them easy to pull on and off. Polyurethane midsole. Thermo urethane outsole. Imported.

NOTE: This item is excluded from promotional discounts.
Item 190299
Price $130.00

Moloa Kohana Ii Leather Slip Ons From OluKai®: These slip-ons brilliantly captures the Aloha comfort of being barefoot and the excellent support of the iconic huarache style. Full-grain leather uppers feature unlined construction for a more breathable and softer feel. The uppers also have laser perforations in the forefoot and elastic gore fit panels. Removable footbeds with polyurethane gel insert and natural cork cover. Rubber outsoles with full-grain leather foxing. Versatile drop-in heels so you can wear them as shoes or slides. Handsewn whip stitching and embroidered logo detail. Imported.

NOTE: This item is excluded from promotional discounts.

Item 190470
$75.00
4.45

(11)

Leather Slip Ons from Brewshoes®: Exclusive to Territory Ahead, the rich leather uppers are hued like the popular Rogue Ales; the shoe style is an unlined slip-on cruiser with elastic gores for a good fit. Slip-resistant outsoles with beer bottle pattern. Imported.

4.45

(11)

4.45

(11)

Item 190947
Price $165.00

Jerez Leather Moccasins From Pikolinos: Lightweight, flexible and comfortable with smooth leather uppers and signature stitching details. Goring for flex at the instep. Removable leather insoles and natural rubber outsoles for flex, durability and grip. Imported. European Whole Sizes: 41-46. (EU41=8-8.5, 42=9, 43=9.5-10, 44=10.5, 45=11-11.5, 46=12).

Item 190647
Price $185.00

Oscar Chukka Boots from Josef Seibel®Discreet, comfortable rubber lug sole. Removable footbed. Brushed poly interior lining for warmth. Waxed cotton laces. Dark Brown features contrasting textured leather heel cap and tongue. Black features a dusty matte finish. Imported. European Whole Sizes: 41-47. (EU41=8-8.5, 42 = 9, 43 = 9.5-10, 44 = 10.5, 45 = 11-11.5, 46 = 12, 47 = 13).

NOTE: This item is excluded from promotional discounts.

Item 190999
$260.00
$199.00
Save 23%

Stoneman Boots From UGG®: Discover the ultimate in comfort and wearability with these rugged UGG boots. They're built to weather the elements with waterproof suede uppers and Vibram EVA rubber outsoles. Lined in genuine sheepskin. Imported.

Item 190950
$125.00
$100.00
Save 20%

Merrimac Suede Moccasins From Eastland®: A super-comfortable hybrid of your favorite slipper and a classic boat shoe, updated with a suede upper featuring heavy stitchwork. Shock-absorbing plantation crepe sole offers cushioning and traction. Leather lined. Rawhide laces. Imported.

Item 190949
Price $135.00

Arizona Sandals From Birkenstock®: These keep your feet comfortable and dry, and they require no break-in time. Soft suede straps and footbed liners. Flexible, shock-absorbing soles. Unlike previous Birkenstock® versions, these feature padded, contoured cork footbeds that conform to the shape of your feet from day one. Raised toe bars. Made in Germany.

NOTE: This item is excluded from promotional discounts.

Item 190948
Price $100.00

Nylon Web Sandals From Teva®: Super comfortable and water friendly. Nylon web uppers have adjustable Velcro® straps for the perfect fit. Durabrasion Rubber™ outsole for traction. Nylon shank for stability. Padded heel strap. Microban® zinc based anti-microbial protection. Compression molded EVA midsole. Encapsulated Shoc Pad for shock absorption. Imported.

NOTE: This item is excluded from promotional discounts.

Item 190946
$110.00
$88.00
Save 20%

Cabot Leather Fisherman Sandals From Born®: Handcrafted using Opanka® construction (the upper is handsewn to the bottom). Soft leather upper with leather lining. Leather sock liner keeps foot dry. Midsole is made of dual density foam with arch support for comfort, support and flexibility. Cork-infused rubber sole for lightness and long-lasting wear. Imported. 

Item 190945
$145.00
$101.50
Save 30%

Tarifa Leather Slides From Pikolinos: Smooth, vegetable-tanned leather is hand-burnished and hand-whipstitched. With contoured, leather-wrapped footbed and EVA midsole for comfort and shock absorption. Imported. European Whole Sizes: 41-47. (EU41 = 8-8.5, 42 = 9, 43 = 9.5-10, 44 = 10.5, 45 = 11-11.5, 46 = 12, 47 = 13).

Item 190902
$120.00
$59.00 - $99.00
Save up to 51%

Atene Moccasin from Bussola®: Lightweight, all-day comfort in a classic moccasin with ridged traction soles in contrasting colors. Imported. Sold in European whole sizes.

Product Size Conversions
EU 41 42 43 44 45 46 47
US 8-8.5 9 9.5-10 10.5 11-11.5 12 13

Item 190901
$125.00
$89.50
Save 28%
5.05

(1)

Kirkham Lace Ups From Ahnu®Styled with fine leather uppers, rugged traction soles and multi-needle stitching. Padded tongue and ankle collar for comfort. Numentum™ technology centers your foot for an efficient, stable stride. Imported.

NOTE: This item is excluded from promotional discounts.

5.05

(1)

5.05

(1)

Item 190815
$158.00
$138.00

West Driver Mocs From Frye®: Smooth nubuck leather with rustic Western detailing: contrast stitching on the vamp and heel, and a rubber-pod sole. Leather-lined with a cushioned footbed. Imported.

Item 190793
$160.00
$59.00
Save 63%
3.35

(6)

Sansome II Lace Ups from Ahnu®: Offering the comfort and support of athletic shoes and the style of fine leather, these lace ups feature rugged soles and rich, full-grain leather uppers. The weathered, tonal light and dark brown marks on the toe add to the ruggedness and lived-in character. And Numentum™ technology centers your foot for an efficient, stable stride. With padded tongue and ankle collar, and multi-needle stitch reinforcement. Imported.

NOTE: This item is excluded from promotional discounts.

3.35

(6)

3.35

(6)

Item 190721
$175.00
$119.00
Save 32%
4.15

(8)

Stanton Earthy Sneakers From Josef Seibel® Exclusively for Territory Ahead: A Euro-styled, earth-friendly quasi-sneaker built for all-day comfort. Crafted with vegetable-tanned nubuck and suede leather upper; a rubber, cork and polyurethane outsole; and a recycled footbed. Support comes via the integrated flex rolling system; and the antibacterial footbed helps eliminate unwanted odors. Imported.

NOTE: This sneaker has a wider fit.

4.15

(8)

4.15

(8)

Item 190535
Price $175.00

Po'okela Leather Sandals From Olukai®: When you're on island time, you need footwear to match the relaxed pace. These are the next best thing to going barefoot. Cool island vines are laser-etched onto the supple leather footbeds, with reinforced stitching details. Compression-molded EVA midsoles. Traction bottoms for better grip. Imported.

NOTE: This item is excluded from promotional discounts.

Item 190491
Price $134.00

Vent Hybrid Boiled Wool Slip On Shoes from Giesswein: The shoe that wears like a clog but feels like a cozy slipper. All-season, naturally breathable boiled wool upper wraps your foot in superior comfort. With removable contoured cork footbed. Reinforced stitching at the collar with adjustable bungee cord. Slip-resistant, waterproof crepe outsole. Imported. European Whole Sizes: 41-46. (EU41 = 8-8.5, 42 = 9, 43 = 9.5-10, 44 = 10.5, 45 = 11-11.5, 46 = 12-12.5).

Item 190484
$150.00
5.05

(1)

Nolan Lace Ups from Josef Seibel®A new take on casual lace-up oxfords with smooth leather uppers and great stitching details. With anatomical footbeds and rubber insoles. Best of all, these comfort shoes require no break-in time. Imported. European Whole Sizes: 41-47. (EU41 = 8-8.5, 42 = 9, 43 = 9.5-10, 44 = 10.5, 45 = 11-11.5, 46 = 12, 47 =13).

NOTE: This item is excluded from promotional discounts.

5.05

(1)

5.05

(1)

Item 190477
$110.00
$95.00
4.55

(2)

Asten Unconstructed Chukka Boots From Børn®: A casual chukka boot style with the comfort and flexibility of your favorite sneakers. Opanka® handsewn construction. Suede uppers, fabric linings and tucker board shanks. Rubber outsoles. 1.25" heels. Imported.

4.55

(2)

4.55

(2)

Item 190471
$95.00
$85.00

Sawyer Lightweight Leather Slip Ons From Børn®: Ideal travel shoes with laid-back comfort and gussets for easy on/off. Featuring full-grain leather uppers, suede linings and EVON outsoles. Steel shanks. Opanka® handcrafted construction. 1" heels. Imported.

Item 190220
Price $130.00

Moloa Kohana Leather Slip Ons From Olukai®: An easy, lightweight shoe with smooth leather upper, rubber sole and cork footbed lining. Long lasting footbed is removable. Versatile Drop-In Heel™ to wear it as a shoe or slide. Imported.

NOTE: This item is excluded from promotional discounts.

Item 190219
$85.00
5.05

(2)

Nohea Mesh Slip Ons From Olukai®: "Nohea" is Hawaiian for "handsome," and you'll feel just that when you wear these feet-friendly, water-friendly slip-ons. Best of all, the collapsible heels let you wear them around town as traditional shoes or to the beach as easy slip-ons. Breathable mesh uppers, removable sole inserts, faux suede lining and contrast gore at the sides. Imported.

NOTE: This item is excluded from promotional discounts.

5.05

(2)

5.05

(2)

Item 190214
$175.00
$140.00
Save 20%

Jerez Micro-Perforated Driving Moccasins From Pikolinos: Slip into these super soft mocs, hit the gas and never look back. Flexible microperforated leather uppers and handstitched trim detail combine to create a unique, handcrafted look. Goring for flex at the instep. Removable leather insoles and natural rubber outsoles with driver heels for flex and grip. Weight: 9 oz.  Imported. European Whole Sizes: 41-47. (EU41 = 8-8.5, 42 = 9, 43 = 9.5-10, 44 = 10.5, 45 = 11-11.5, 46 = 12, 47 = 13).

Item 190211
$140.00
$110.00
Save 21%

Perforated Suede Comfort Sneakers from Josef Seibel®Perforated suede and leather uppers for a great look and breathable comfort. With anatomical footbeds. Rubber insoles. Imported. European Whole Sizes: 41-47. (EU41 = 8-8.5, 42 = 9, 43 = 9.5-10, 44 = 10.5, 45 = 11-11.5, 46 = 12, 47 = 13).

NOTE: This shoe features a wider European toe box for added comfort and fits true-to-size on the rest of the foot.

Item 190201
$125.00
$99.50
Save 20%
5.05

(1)

Mac Pull-on Boots From Børn®Handsomely shaped from natural full-grain leather with leather lining, rubber outsole and steel shank. Opanka hand-sewn construction. Heel height: 1¼". Imported.

5.05

(1)

5.05

(1)

Item 190640
$115.00
$99.00

Galen Leather Slip Ons from Børn®: These casual slip-ons are ready for full-time relaxation. Soft, premium leather uppers with hidden gore stretch panels at the instep. Cushioned microsuede insoles for moisture-free comfort. Shock-absorbing rubber outsoles. Reinforced leather heels. 1.25" heel height. Imported.

Item 190636
$115.00
$99.00

Galen Leather & Suede Slip Ons from Børn®: These casual slip-ons are ready for full-time relaxation. Soft, premium leather or suede uppers with hidden gore stretch panels at the instep. Cushioned microsuede insoles for moisture-free comfort. Shock-absorbing rubber outsoles. Reinforced leather heels. 1.25" heel. Imported.

Item 190625
Price $130.00

Fulton Waterproof Sneakers from Ahnu®: These have the look of a hiking boot and the comfort of a sneaker. Waterproof oiled nubuck uppers with suede panels at the back. Padded tongue, cotton twill lining and removable footbed. Sporty speed laces (change to a tone-on-tone look with the complimentary twilight-colored laces). Contrast rubber bottoms. Imported.

NOTE: This item is excluded from promotional discounts.

Item 190622
Price $125.00

Balboa Waterproof Suede Sneakers from Ahnu®These rugged lace-ups feature durable, waterproof suede uppers with contrast leather trim. Removable, sculpted EVA footbeds and EVA midsoles for cushioning and shock absorption. Lugged outsoles with non-marking rubber for traction and wear. Moisture-wicking synthetic mesh lining. Imported.

NOTE: This item is excluded from promotional discounts.

Item 190608
$110.00
$99.00

Sandor Lace Up Oxford Shoes from Børn®You'll be so glad you wore these, especially if you're at the airport. The flexible gores at the sides of the heels make them easy to put on and take off. Full-grain leather uppers with great stitching details. Hand-sewn Opanka® construction with leather lining and cushioned footbed. EVON soles. Approx. 1" heel height. Imported. 

Item 190518
Price $110.00

Nohea Leather & Canvas Sneakers from OluKai®: They have the look of a shoe with the comfort of a sneaker, and the uppers are a mix of antiqued leather with nylon canvas. Removable sole inserts. Rubber outsoles. Versatile Drop-In Heel to wear as a shoe or a slide. Waxed cotton laces. Imported.

NOTE: This item is excluded from promotional discounts.

Item 190516
Price $140.00

Kupono Nubuck Chukka Sneakers from OluKai®When you can't decide between chukka boots or sneakers, get both with the Kupono! The oiled nubuck uppers are naturally weather-resistant, and the EverFit contoured footbeds are removable and washable. Rubber outsoles. Woven two-tone nylon laces. Imported.

NOTE: This item is excluded from promotional discounts.

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