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.

Sort By
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 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 191103
$110.00
Mano Mesh Lace Up Shoes from OluKai®: Versatile in water or on land, this cool-wearing shoe features a breathable open mesh upper with a lightweight, quick-drying lining. Elastic quick-lace system for easy on and off. Lightweight, anatomical, quick-drying footbed. Non-marking rubber outsole. Embossed OluKai logo. Imported.

NOTE: This item is excluded from promotional discounts.
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

(3)

5.05

(3)

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 190470
$75.00
4.35

(17)

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

(17)

4.35

(17)

Item 191102
$110.00

Dasalo Leather Slip On Shoes from Oliberté: Enjoy all-day comfort in these casual slip-ons with premium leather uppers. Leather lining. Water-based PU comfort insole with heel stabilizer. Removable footbed features a cool map print. Natural rubber outsole with wedge. Made in Ethiopia. Fair Trade Certified. European Whole Sizes: 41-46. (EU41=8, 42=9, 43=10, 44=11, 45=12, 46=13).

Item 191200
$335.00

Lewis Leather Cowboy Boots from Lucchese®: Lucchese Bootmakers have been creating iconic handmade boots since 1883. The distressed leather gets better the more you wear them, and the rounded toes and classic stitching and pull straps give them major swagger. Leather linings and fully padded footbeds provide legendary comfort. Goodyear welt construction. 12.5" shaft height; 1.75" stacked heels. Handmade in Mexico.

Item 191104
$120.00

Arrowood Waterproof Sneakers from Teva®: These cool, easy-wearing sneakers offer waterproof protection and feature the featherweight comfort of Floatlite™ technology. Foam construction is ultralight and durable with improved rebound function and excellent traction. Nylon mesh interior. Contrast cushioned insole and collar. Contrast speckled rubber sole. Imported.

NOTE: This item is excluded from promotional discounts.

Item 144039
$95.00

Finley Leather Belt from Trask™: Crafted of sturdy American steer leather with a unique grain and rugged character. It has the worn appeal of a vintage bomber jacket, and pairs effortlessly with jeans. Antiqued nickel buckle. 1 3/8" wide. U.S. made.

NOTE: This item is excluded from promotional discounts.

Item 191111
$210.00

Sawyer Leather Moccasins from Trask: Made of hand-selected American steer leather with hand-knotted, American-made genuine rawhide trim. Foam-cushioned footbed with leather-covered insole for superior all-day comfort. Sheepskin lined. Buffed leather outsole with rubber inset for flexibility. Stacked leather heel with half rubber toplift. 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 190647
$185.00
5.05

(1)

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.

5.05

(1)

5.05

(1)

Item 190648
$499.00
$449.50
Save 10%
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 features 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.

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 190716
$195.00
$174.50
Save 11%
4.35

(3)

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).
4.35

(3)

4.35

(3)

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 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 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 190293
$99.00
5.05

(1)

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.
5.05

(1)

5.05

(1)

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)

5.05

(2)

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 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 190625
$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 190947
$165.00
$115.00 - $165.00
Save up to 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

(2)

Item 190636
$115.00
$57.50 - $79.00
Save up to 50%
5.05

(1)

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.

5.05

(1)

5.05

(1)

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

(1)

Item 190619
$125.00
$62.50 - $105.00
Save up to 50%
5.05

(1)

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.

5.05

(1)

5.05

(1)

Item 191101
$175.00

San Telmo Leather Slip On Shoes from Pikolinos®: Smooth leather uppers with split toe and cool stitching details. Twin elastic gores for an ideal fit. Textile lining and rubber sole. Removable cushioned insole. 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 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 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)

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 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 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.
5.05

(1)

5.05

(1)

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)

  • Refine by:
  • Clear
    Type
    • Shoes
    • Boots
    • Sandals
    • Moccasins
    • Oxfords
    • Sneakers & Athletic
    • Slippers
  • Clear
    Style
    • Leather
    • Slip-On
    • Lace-Up
    • High-Top
    • Pull-On
    • Chukka
    • Low-Top
  • Clear
    Size
    07
    07.5
    08
    08.0
    08.5
    09
    09.0
    09.5
    10
    10.5
    11
    11.5
    12
    13
    34
    40
    41
    42
    43
    44
    45
    46
    47
    8
    8.5
    9
    9.5
  • Clear
    Size Range
    • Regular
  • Clear
    Color
    BROWN
    BLACK
    NEUTRAL
    GREY
    RED
    GREEN
    PATTERN
  • Clear
    Price
    • Under $50
    • $50 to $74.99
    • $75 to $99.99
    • $100 to $149.99
    • $150 & Above
  • Clear
    Rating
    4 Stars and Up
    3 Stars and Up
    2 Stars and Up
    1 Stars and Up
  • Clear
    Spotlight Styles
    • New Arrivals
  • Clear
    Special Offers
    • Clearance
    • Sale