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 190313
Price $39.50
5.05

(1)

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.
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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 190300
Price $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 190311
Price $120.00
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. 
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Item 190293
Price $99.00
Rocky Leather Sandals from Jambu®: Premium, tumbled nubuck leather uppers are anchored by two sliding grosgrain tabs for extra comfort and easy adjustment. The feel is open and the look is minimal, but the security of fit and movement is substantial. Contoured EVA cushioned footbeds. Partially recycled rubber All-Terra outsoles. Imported.

NOTE: This item is excluded from promotional discounts.
Item 190305
Price $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 190307
Price $175.00
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 190302
Price $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 190294
Price $110.00
5.05

(2)

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).

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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.

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Item 190296
Price $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 190306
Price $170.00
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).

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Item 190304
Price $150.00

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 190303
Price $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 190947
Price $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).

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Item 190519
Price $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.

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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.

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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 190565
Price $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 190301
Price $195.00

Beck Leather Sneakers From Trask™: Luxuriously supple Norwegian elk uppers with burnished full-grain cap toes are channel-stitched to rubber outsoles for high-wear durability, even at flex points. Leather lining and sock. Shock-absorbing EVA insole for cushioned comfort. Round rawhide leather laces. Imported.

NOTE: This item is excluded from promotional discounts.

Item 190292
Price $120.00

Ahnu® Coburn Waterproof Low Hikers: 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 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 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 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 190516
Price $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.

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Item 190298
Price $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 190718
$75.00
$22.50
Save 70%
Hookset Canvas Slip On From Timberland: The perfect vacation shoe to keep you in a relaxed frame of mind. Crafted using 100% organic washed cotton canvas for lightweight comfort and durability. With an eco-conscious, natural latex footbed and outsole for traction. Elastic gore for easy on/off. Imported. 
Item 190312
Price $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 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 190946
$110.00
$88.00
Save 20%
5.05

(1)

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. 

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Item 190200
$99.00 - $110.00
$32.50 - $99.00
Save up to 70%

Harmon Leather Slip On From Børn®Enjoy superior comfort in a casual, moccasin-style slip-on. Crafted with full-grain leather upper, leather lining, rubber outsole and steel shank. Imported.  

Item 190906
$125.00
4.55

(4)

Atene Lace-up Sneakers from Bussola®Leather upper with suede detailing at the toe. Leather lining keeps feet cool and dry. With rubber outsole and traction at bottom. Cushioning at ankle for extra comfort and support. Imported. European Whole Sizes: 41-46. (EU41=8-8.5, 42=9-9.5, 43=10-10.5, 44=11-11.5, 45=12-12.5, 46=13-13.5).
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Item 190716
Price $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).
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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 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 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).

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