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

(2)

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

(2)

5.05

(2)

Item 190294
$110.00
4.35

(3)

Dakugo Leather Sneakers from Oliberté: Designed for all-day comfort with premium leather uppers detailed with woven strips and perforations. Featuring a leather lining and comfort insole with heel stabilizer. Natural rubber sole with reinforced sidewall stitching. Made in Ethiopia. Fair Trade certified. European Whole Sizes: 41-46. (EU41=8, 42=9, 43=10, 44=11, 45=12, 46=13).

4.35

(3)

4.35

(3)

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 190716
$195.00
$145.00 - $195.00
Save up to 26%
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)

4.05

(2)

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

(16)

Item 190627
$170.00

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.

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 190622
$125.00
$89.00 - $125.00
Save up to 29%

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 190625
$130.00
$90.00 - $130.00
Save up to 31%

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 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 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 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 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 190299
$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 190947
$165.00
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

(2)

Item 190302
$295.00

Riddick Leather Driving Moccasins from Trask™: The classic moccasin gets an upgrade with dip-dyed woven calfskin, a process that imparts intensely rich color and enhanced softness. A sturdy Vibram® rubber outsole ensures walking comfort and durability. Leather lining and sock. Foam-cushioned insole. Made in Italy.

NOTE: This item is excluded from promotional discounts.

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 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 190303
$245.00

Blaine Perforated Suede Slip-Ons from Trask™: A versatile shoe with water-resistant suede upper and dual gore insets for easy on and off. Partially leather lined with leather sock liner for breathability. EVA cushioned footbed for added comfort. Shock-absorbing natural Latex® rubber outsole sourced from sustainably harvested trees. 1" stacked heel. Imported.

NOTE: This item is excluded from promotional discounts.

Item 190313
$39.50
5.05

(2)

Beach Arizona Sandals from Birkenstock®: The Birkenstock sandals you can get wet! Super-lightweight EVA plastic keeps your feet comfortable and dry. Featuring padded contoured footbeds that conform to the shape of your feet. Two adjustable buckles. Raised toe bars. Made in Germany. European Whole Sizes: 41-46, (EU41 = 7.5-8, 42 = 8.5-9, 43 = 9.5-10, 44 = 10.5-11, 45 =11.5-12, 46 = 13).

NOTE: This item is excluded from promotional discounts.
5.05

(2)

5.05

(2)

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 190632
$150.00
$105.00
Save 30%

Ridgecrest Waterproof Trail Sneakers from Ahnu®: Rock the trail and stay balanced with Numentum® Hike technology that centers and guides your foot, whether or not you have a pack. High density EVA plugs at the heel mean Ahnu boots feel like athletic shoes while offering the heel stability you’ll find in the most rugged hikers. With a removable footbed. Waterproof.

NOTE: This item is excluded from promotional discounts.

Item 190306
$170.00
$165.00
3.05

(1)

Leather Chukka Boots from El Naturalista: Full grain leather uppers are supersoft, and rubber outsoles ensure all-day comfort. Anatomically designed insoles fit the contour of your foot and the rubber offers the flexibility required to absorb footsteps. Fully leather lined. With waxed cotton laces and blanket stitch details. Imported. European Whole Sizes: 40-46. (EU40 = 7-7.5, 41 = 8-8.5, 42 = 9, 43 = 9.5-10, 44 = 10.5, 45 = 11-11.5, 46 =12).

3.05

(1)

3.05

(1)

Item 190305
$145.00
Ensenada Leather Huarache Sandals from BedStu®: Vegetable-dyed leather is expertly hand woven at the uppers and back with an adjustable buckle at the ankle. Cushioned insoles and sturdy Goodyear® welts. Handcrafted in Mexico.
Item 190304
$150.00
$145.00

Whipstitch Suede Shoes from El Naturalista: Full grain suede uppers are supersoft and unlined for flexibility, and rubber outsoles ensure all-day comfort. Anatomically designed insoles fit the contour of the foot and the rubber offers the flexibility required to absorb footsteps. With waxed cotton laces and blanket stitch details. Imported. European Whole Sizes: 40-46. (EU40 = 7-7.5, 41 = 8-8.5, 42 = 9, 43 = 9.5-10, 44 = 10.5, 45 = 11-11.5, 46 =12).

Item 190516
$140.00
4.05

(2)

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.

4.05

(2)

4.05

(2)

Item 190815
$158.00
$138.00
Save 13%

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 190300
$130.00
Mea Ola Leather Sandals from OluKai®: "Mea Ola" (May-Ah Oh-La) is Hawaiian for "Creature," and you'll love the creature comforts of these amazingly cool sandals. Full-grain antiqued leather straps feature handsewn canoe lash whipstitch details. Moko laser artwork on the footbeds with embroidered logo. Compression-molded EVA midsoles wrapped in premium full-grain leather. Leather outsoles with non-marking rubber traction pods. Imported.

NOTE: This item is excluded from promotional discounts.
Item 190220
$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 190473
$130.00
$110.00
Save 15%
5.05

(1)

Ohana Nubuck Lace-up Shoes From Olukai®The perfect casual shoes that offer superior comfort and durability. Features Drop-In Heel™ to wear as a shoe or a slide. Antiqued, waxed nubuck uppers, lined with moisture-wicking Dri-Lex® microfiber. EverFit, removable and washable contoured footbeds. Rubber outsoles with full-grain leather foxing. Imported.

5.05

(1)

5.05

(1)

Item 190296
$105.00

Sogal Leather Slip On Sneakers from Oliberté: A cool hybrid of a sneaker and slip-on shoe with premium leather upper. Featuring a leather lining and comfort insole with heel stabilizer. Natural rubber sole with reinforced sidewall stitching. Made in Ethiopia. Fair Trade certified. European Whole Sizes: 41-46. (EU41=8, 42=9, 43=10, 44=11, 45=12, 46=13).

Item 190619
$125.00
$105.00
Save 16%

Karl Leather Clogs from Dansko®: Legendary Dansko stapled clogs launched a comfort generation. Leather uppers and rubber soles. Contoured midsoles keep your feet comfortable, supported and secure with firm foot and arch support. Exceptional shock absorption that's comparable to athletic footwear. Approx. 2.25" heel height; approx. .75" platform. Imported. European Whole Sizes: 42-47. (EU42 = 8.5-9, 43 = 9.5-10, 44 = 10.5-11, 45 = 11.5-12, 46 = 12.5-13, 47 = 13.5-14).

NOTE: This item is excluded from promotional discounts.

Item 190605
$115.00
$105.00
Save 9%
4.55

(2)

Jax Chukka Boots from Børn®Full-grain leather uppers feature burnished toes and waxed cotton laces. Hand-sewn Opanka® construction with leather lining and rubber traction sole. Cushioned insole. Approx. 1" heel height. Imported. 

4.55

(2)

4.55

(2)

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 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 190524
$99.50

Open Heel Shoes From Glerups®: Designed for men and women, these clog-style slip-ons form to your feet for luxurious next-to-skin comfort. Handmade from 100% natural Merino and Gotland wool. Soft enough to wear with bare feet for year 'round indoor comfort and breathability. The distinctively Scandinavian design utilizes eco-friendly dyes and a soft, vegetable-tanned leather sole. Made in Denmark. European Whole Sizes 42-47. (EU42 = 9, 43 = 9.5-10, 44 = 10.5, 45 = 11, 46 = 12-12.5, 47 = 13).

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