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 190519
$375.00
5.05

(3)

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.

5.05

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Item 190833
$120.00
Akahai Nubuck Slip Ons from OluKai®: Highly crafted, but fully laid back, the Akahai is built for the comfort of island time, all the time. Premium, soft nubuck leather uppers are oiled and waxed with a minimal lining. Drop-In Heel™ for wearing as a shoe or slide. Removable and washable, dual-density anatomical PU footbed. Rubber outsole for flexibility and traction. Imported.

NOTE: This item is excluded from promotional discounts.
Item 190648
$499.00
5.05

(1)

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.

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(1)

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Item 190647
$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 190848
$185.00
Nubuck leather uppers feature Topdry Tex membrane for 100% waterproof protection. Removable memory foam leather insoles. Leather linings. Polyurethane flexible outsoles. Heel height: 1.25". 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 190849
$335.00
Cole Leather Cowboy Boots from Lucchese®: Full-grain leather uppers boast a dramatic corded design and stitching on the shaft. With a leather lining, leather cushioned insole and leather outsole with rubber cap stacked heel. Narrow rounded toe. Imported.
Item 190611
$170.00
5.05

(2)

Tamarack Waterproof Boots from Ahnu®: A great cold-weather boot that offers warmth without bulk. Waterproof leather upper with cozy, faux shearling lining. Removable footbed with a wool top layer and 200-gram Thinsulate® inside layer for extra insulation. Wide side gores for easy on and off. Slip-resistant lug sole. Rubber toe protector. Imported.

NOTE: This item is excluded from promotional discounts.
5.05

(2)

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Item 190625
$130.00
$65.00 - $130.00
Save up to 50%

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 190843
$200.00
OluKai's take on the classic chelsea boot features full-grain leather uppers with elastic gore panels for easy on and off. Leather and microfiber lining. Removable, dual-density anatomical PU footbed. Durable TR outsole with leather welt and forefoot traction pods. Hand-brushed heel with logo. Shaft height: 7.25". Imported. Sizes: 8-12 (including half sizes), 13.
Item 190845
$150.00
Inspired by the bold landscape of Hawaii's Big Island, featuring high-character, heavily waxed, smooth and tumbled nubuck leather uppers with suede collar accents. Moisture-wicking microfiber lining. Removable, dual-density anatomical PU footbed with polyurethane gel insert. All-weather, non-marking rubber outsole with full-grain leather wrap. Wide ankle opening and roomy toe box. Hand-sewn moc stitching. Shaft height: 4.5". Imported. Sizes: 8-12 (including half sizes), 13.
Item 190716
$195.00
4.05

(2)

Pikolinos Chile Pebble Grain Lace Up Boots:A versatile hiking-style boot featuring pebble-grain leather uppers with a buff finish and waterproof stain protector. Leather and fabric lining. Padded suede collar for extra comfort and support. Synthetic outsole. Removable insole. Imported. European Whole Sizes: 41-46. (EU41 = 8-8.5, 42 = 9, 4 3= 9.5-10, 44 = 10.5, 45 = 11-11.5, 46 = 12-12.5).
4.05

(2)

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Item 190622
$125.00
$62.50 - $125.00
Save up to 50%

Ahnu®Balboa Waterproof Suede SneakersThese 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 190470
$75.00
4.35

(16)

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.

4.35

(16)

4.35

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Item 190627
$170.00
5.05

(1)

Willow Comfort Sneakers from Josef Seibel®: Nubuck leather upper features exemplary stitching with a padded collar for all-day comfort. Textile lining with removable footbed. Lightweight, flexible, hard-wearing outsole. Rubber traction sole. 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)

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Item 190565
$175.00
5.05

(1)

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.
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Item 190465
$165.00

Coburn Waterproof Boots from Ahnu®: The boot equivalent of an all-terrain vehicle... these rugged hikers are designed to stand up to wet and dry conditions. Durable, full-grain, waterproof leather uppers with rubber toe protectors, lined with breathable eVent® bootie and moisture wicking mesh. Numentum® Hike technology centers and guides the foot to promote balance. Gusseted tongue helps keep water and debris out. Non-marking rubber outsoles for superior grip and traction. Imported.

NOTE: This item is excluded from promotional discounts.

Item 190837
$170.00
Badajoz Leather Slip Ons from Pikolinos®: A great comfortable slip-on that dresses up or down. Oiled leather uppers with suede accents. Split toe with reinforced stitching. Leather lining. Flex rubber soles. Elastic goring for easy on and off. Imported. 
Item 190628
$165.00
Boston Shearling Lined Clogs from Birkenstock®: So cozy you'll live in them all day and night! Designed for indoor/outdoor wear with supple suede uppers. Soft footbed features a foam layer inserted between the cork layer and suede liner for durable comfort. Shearling lining for extra warmth. Flexible EVA soles are lightweight, durable and shock absorbing. Imported. European Whole Sizes: 41-42. (EU41 = 7.5-8, 42 = 8.5-9).

NOTE: This item is excluded from promotional discounts.
Item 190835
$125.00
Jacques Low Top Leather Sneakers from Børn®: These have the look of a chukka boot with the comfort of a sneaker. Soft, handsewn Italian leather uppers. Lining made of sueded, moisture-wicking tech fabric and leather. Multi-density foam footbed covered in a tech fabric – it offers arch support as well. Imported.
Item 190851
$120.00
Adibo Suede Chukka Boots from Oliberté®: Go anywhere in these incredibly comfortable chukkas featuring suede uppers that will look and feel better with age. Lightly padded collar, stitch-down design around the base, water-based PU comfort insole features a map design (you'll have the world at your feet!) with heel stabilizer. Natural crepe rubber outsole and wedge. Imported. 
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 190830
$110.00
Joel Lace Up Oxford Shoes from Børn®: Oiled full-grain leather uppers with Opanka® hand-crafted construction. Suede and leather lining for soft comfort. Rubber sole for lightness and long-lasting wear. Heel height: 1". Imported.
Item 190948
$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 190608
$110.00
$55.00
Save 50%
4.05

(1)

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. 

4.05

(1)

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(1)

Item 190815
$158.00
$79.00
Save 50%

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 190298
$229.00
Keith Runner Perforated Suede Sneakers from Frye®: These vintage-inspired running shoes feature buttery soft uppers that are perforated for breathability on hot days. Contrast padded leather tongue and back heel. Traction rubber soles. Leather lining. Rawhide leather laces. Imported.

Note: This item is excluded from promotional discounts.
Item 190214
$175.00
$87.50
Save 50%
5.05

(1)

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).

5.05

(1)

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Item 190947
$165.00
$115.00
Save 30%
3.05

(2)

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).

3.05

(2)

3.05

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Item 190610
$125.00
$62.50
Save 50%
Lumber Up Fleece Lined Boots from Eastland®: Workman-style boots provide warmth without being heavy. Pebbled leather uppers with durable nylon corded laces. Fleece-lined for extra warmth and comfort. Triple reinforced hand stitching for extended durability. Cushioned insoles. Lightweight rubber soles. 1" heels. Imported.
Item 190640
$115.00
$57.50
Save 50%
4.05

(3)

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.

4.05

(3)

4.05

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Item 190211
$140.00
$70.00
Save 50%

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 190493
$92.00
$46.00
Save 50%

Andau Boiled Wool Slippers From Giesswein: The most comfortable slippers you'll ever wear! Super soft boiled wool is densely woven for natural warmth and odor resistance. Flexible, removable footbeds ensure a personalized fit. Side elastic gores for easy on and off and rubber bottoms for traction. Imported. European Whole Sizes: 41-46. (EU41 = 8, 42 = 9, 43 = 10, 44 = 11, 45 = 12, 46 = 13).

Item 190636
$115.00
$57.50
Save 50%

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 190312
$140.00
Boston Suede Clogs from Birkenstock®: Classic-styled, open-back clog offers all-day comfort with an adjustable strap for a more personalized fit. Suede/leather upper with suede-lined cork footbed and shock-absorbing EVA outsole for better-than-barefoot comfort. Raised toe bar, footbed form, arch support and deep-heel cup with footbed liner combine to align your foot naturally for even weight distribution and proper support. Made in Germany.

NOTE: This item is excluded from promotional discounts.
Item 190949
$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 190307
$175.00
$135.00
Save 23%
Friction Hiker Sneakers from Millet®: This rugged-looking, alpine-style lace-up sneaker is comfortable, durable and versatile for hiking or wearing around town. Reinforced leather upper with waterproof Gore-Tex® membrane, and rubber at the toe and heel. Dual-density, shock-absorbing midsole. Removable insole with shock-absorbing footbed. Vibram® multigrip outsole adapts perfectly to mixed or unstable terrains. Imported. 
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