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 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 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 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)

5.05

(1)

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 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 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 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)

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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 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 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 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 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 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 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 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 190214
$175.00
$140.00
Save 20%
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)

5.05

(1)

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 190608
$110.00
$74.00 - $74.50
Save up to 33%

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 190520
$200.00
$190.00
Save 5%

Pikolinos Mackenzie Moc High Tops: A cool, rugged-looking high-top moccasin with burnished leather upper and suede accent trim. Rubber traction sole. Padded collar. Fully leather lined. 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 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 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. 
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 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 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

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Item 190475
$158.00
$109.00
Save 31%

Innsbruck Boiled Wool Slip On Shoes From Glesswein: Enjoy all-day comfort and support with naturally breathable boiled wool uppers, removable contoured cork footbeds and elastic side gores. Flexible, durable crepe soles. Imported.

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 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 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
Save 14%
3.55

(2)

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.

3.55

(2)

3.55

(2)

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 190636
$115.00
$79.00
Save 31%

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 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 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 190621
$120.00

Moloa Shearling Slippers from OluKai®: Super cozy slippers feature a warm, soft shearling lining with a removable insert, and the collapsible heel lets you wear them as a slipper or a slide. Nubuck leather uppers. Rubber outsoles with laser-etched logo. Side gores for easy on and off. Great stitching details. Imported.

NOTE: This item is excluded from promotional discounts.

Item 190518
$110.00
5.05

(1)

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.

5.05

(1)

5.05

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Item 190311
$120.00
$105.00
Save 13%
5.05

(1)

Hugh Leather Fisherman Sandals from Børn®: Full-grain leather uppers feature wide, open-weave straps for supreme breathability and comfort. Leather lining. Midsole is made of dual density foam with arch support for comfort, support and flexibility. Adjustable buckle at ankle. Rubber sole for lightness and long-lasting wear. Imported. 
5.05

(1)

5.05

(1)

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