Shoes & Boots

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Item 191121
$245.00
Landry Leather Oxford Shoes from Trask™: American bison leather uppers have a suede-like matte finish for a handsome shoe that dresses up or down. With a leather lining and contrast stitching. Vibram® rubber outsole for extra comfort and traction. Approx. 1" heel. Imported.

 NOTE: This item is excluded from promotional discounts.
Item 191211
$358.00
Bowery Distressed Leather Boots from Frye®: These sturdy, rugged leather boots have a vintage distressed look with a lace-up front and zipper at the side for easy on and off. Leather insole. Rubber outsole with traction bottom. Heel height: 1". Made in Mexico.

NOTE: This item is excluded from promotional discounts.
Item 191143
$225.00
Enjoy the comfort and style of this relaxed loafer, artisan-crafted of hand-selected premium leathers, prized for their unique character and supple feel. The American steer leather has a rugged, vintage character that gains richness with wear. Side-stretch gores for easy on and off. Stitch-out construction. Leather lining. Ortholite®-cushioned footbed with leather/microsuede-covered insole. Vibram® rubber outsole. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191104
$120.00
5.05

(1)

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.

5.05

(1)

5.05

(1)

Item 190470
$75.00
$40.00
Save 47%
4.45

(21)

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.

4.45

(21)

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Item 191101
$175.00
5.05

(1)

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).

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(1)

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(1)

Item 191212
$60.00
Katavi 2 Suede Slides from Teva®: Soft suede uppers with contoured EVA footbeds to support your arches and keep your feet happy. Nylon shanks stabilize and support your feet on uneven terrain. Rugged Durabrasion Rubber outsole stands up to the elements and offers great traction. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191205
$285.00
Larkin Side Zip Waxed Suede Boots from Trask™: Handsome waxed suede uppers give these boots a rugged look, with unique leather trim at the back heel, and cool contrast stitching. Leather lining. Leather insole. Vibram® rubber outsole with traction bottom. Pull-on loop at back. 1.25" heel height. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191120
$180.00
Caceres Leather Oxford Shoes from Pikolinos®: A handsome lace-up shoe that expertly combines city-country and casual-dressy style. Semi-vegetable tanned leather upper from the Pikolinos tannery in Elche, Spain. Hand burnished, hand finished and water resistant. Contrast leather padded collar. Molded synthetic outsole. Leather and textile lining. Removable insole. Heel height: 1". 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 191114
$95.00
$49.00 - $76.00
Save up to 48%
4.35

(3)

Bayne Leather & Suede Sneakers from Børn®: Italian leather and suede are combined to create a casual, yet luxurious, sneaker. Leather lining with leather and cushioned, breathable mesh. Rubber compound outsole. Removable insole in leather and mesh-covered Latex foam. Midsole is handsewn to the leather upper, giving the shoe great flexibility and comfort. Wipe with a damp cloth to clean. Imported.
4.35

(3)

4.35

(3)

Item 191200
$335.00
$170.00
Save 49%

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 191203
$190.00
Caceres Leather Chukka Boots from Pikolinos®: A handsome lace-up boot that expertly combines city-country and casual-dressy style. Semi-vegetable tanned leather upper from the Pikolinos tannery in Elche, Spain. Hand burnished, hand finished and water resistant. Contrast leather padded collar. Molded synthetic outsole. Leather and textile lining. Removable insole. Heel height: 1". 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 191137
$110.00
This is an update to a classic OluKai style, with an upper that’s part natural and durable wool and part premium full-grain leather. Stretch air mesh tongue and gusset. Elastic lacing system for easy on/off and lined with a lightweight, quick-drying single-layer mesh for comfort and breathability. Dual-density anatomical PU footbed with gel insert and a soft, quick-drying single layer textile footbed cover – footbed is removable and washable. Non-marking all-weather rubber outsole. Patented Drop-In Heel® so you can wear it as a sneaker or a slide. Stretch bootie construction for barefoot wear. Imported.

NOTE: This item is excluded from promotional discounts.
Item 190647
$185.00
$139.00
Save 25%
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)

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(1)

Item 190622
$125.00
5.05

(1)

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.

5.05

(1)

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Item 191128
$225.00
$180.00 - $225.00
Save up to 20%
Bradley Perforated Suede Slip Ons from Trask™: Kick back in this more relaxed version of a casual loafer, with perforated suede upper and side-stretch gores for easy on and off. Stitch-out construction. Leather lining. Ortholite®-cushioned footbed with leather/microsuede-covered insole. Vibram® rubber outsole. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191100
$195.00
$150.00
Save 23%
Dalton Leather Slip On Shoes from Trask™: A modern hybrid that combines the sporty feel of a driving moccasin with the laid-back comfort of a sneaker. Supple, Italian sheepskin is washed to enhance softness and create subtle shading. Perforated leather upper and jute braided rope trim for added texture. Double side stretch gores for easy on and off. Leather lining. Leather-covered, EVA-cushioned insole. Nubby rubber outsole. Imported.

NOTE: This item is excluded from promotional discounts.
Item 190518
$110.00
5.05

(3)

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

(3)

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Item 190519
$375.00
$300.00
Save 20%
5.05

(6)

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

(6)

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Item 190565
$175.00
$131.00 - $175.00
Save up to 25%
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)

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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 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 190312
$140.00
$112.00
Save 20%
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 191105
$45.00
$35.00 - $45.00
Save up to 22%
5.05

(1)

Azure Water Friendly Thongs from Teva®: Pool resources... water-ready poly webbing uppers are extremely durable and dry quickly. Molded top sole and midsole for all-day comfort. Rubber outsole. Imported.

NOTE: This item is excluded from promotional discounts.
5.05

(1)

5.05

(1)

Item 191103
$110.00
$100.00
Save 9%
5.05

(1)

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.
5.05

(1)

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(1)

Item 191131
$90.00
Kahu Canvas Sneakers from OluKai®: Breathable and durable nylon upper with rich, full-grain leather accents, lined with a cooling moisture-wicking textile lining. Removable and washable dual-density anatomical PU footbed with polyurethane gel insert and a soft microfiber footbed cover. All-weather, non-marking rubber outsole. Patented Drop-In Heel® lets you wear it as a shoe or a slide. Imported.

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 191119
$170.00
5.05

(1)

Chile Leather Slip On Shoes from Pikolinos®: This super-comfortable slip-on is designed to mold perfectly to your foot's contours, with classic Pikolinos stitching to improve flexibility. Made of semi-vegetable tanned leather with non-slip rubber soles to ensure a confident stride. Synthetic outsole. Removable insole. Gel and foam padded collar. Heel height: 1". 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).
5.05

(1)

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(1)

Item 191201
$180.00
Arrowood Utility Side Zip Boots from Teva®: Waterproof leather upper seals out the elements to keep your feet dry. Neoprene upper tongue and collar for extra comfort. Poly laces and metal D-rings let you adjust for a perfect fit. Dual-color, breathable mesh lining is cool wearing and comfortable. Responsive PU footbed cushions the foot and puts a spring in your step. Float-Lite™ midsole is super durable and feather light. Vibram® molded rubber outsole. Imported.
Item 190621
$120.00
$90.00
Save 25%
5.05

(2)

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.

5.05

(2)

5.05

(2)

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 191147
$95.00
3.05

(2)

Perforated Italian leather upper with canvas side gores for easy on/off. Suede lining. Handmade Opanka construction: midsole is handsewn to the leather upper, giving the shoe great flexibility and comfort. Moisture-wicking footbed. EVON outsole. Wipe with a damp cloth to clean. Imported.
3.05

(2)

3.05

(2)

Item 191148
$115.00
4.55

(2)

This rugged yet refined chukka boot features a smooth Italian suede upper with tonal stitching details. Microfiber lining. Handmade Opanka construction: midsole is handsewn to the suede upper, giving the boot great flexibility and comfort. Removable footbed. Rubber outsole. 1.25” heel height. Wipe with a damp cloth to clean. Imported.
4.55

(2)

4.55

(2)

Item 191117
$110.00
Noho Kai Winter Slippers from OluKai®: "Noho Kai" is Hawaiian for "To live by the sea." Say aloha to your new favorite slippers, designed for indoor or moderate outdoor use. The upper is made of heavily waxed nubuck or soft nubuck leather with a warm and cozy, genuine sheepskin shearling lining. With an anatomical, compression-molded EVA footbed wrapped with soft microfiber. Non-marking rubber outsole with traction pods for flexibility and traction. Use nubuck cleaner and conditioner to clean. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191115
$140.00
Na'i Waterproof Leather Shoes from OluKai®: Enjoy the protection of a boot with the relaxed ease of a slip-on. Premium, waterproof full-grain or waxed nubuck leather and textile upper. Waterproof, breathable membrane, gasket and seam sealing. Dual-density anatomical PU footbed with a polyurethane gel insert. Soft, jersey knit footbed cover features an island-inspired topographical artwork, and is removable and washable. Lightweight, "wet grip rubber" outsole for superior traction and versatility. Heel pull loop for easy on and off. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191130
$60.00
5.05

(1)

Flip Premier Thongs from Teva®: Water-friendly poly webbing upper is extremely durable and dries quickly. Featuring sturdy, three-point thong construction. Responsive Floatlite® footbed cushions the foot and puts a spring in your step. Rubber outsole. Imported.

NOTE: This item is excluded from promotional discounts.

5.05

(1)

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(1)

Stay well grounded, every step of the way, in Territory Ahead’s unique collection of men’s shoes and boots. From cowboy boots and leather sandals to waterproof sneakers and chukka 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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