Shoes & Boots

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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 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 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 191134
$80.00
Nui Leather Thongs from OluKai®: "Nui" (NOO-EE) means "Greatest" on the Hawaiian islands. This unique sandal features high-character, premium full-grain leather uppers that are tumbled or embossed waxed nubuck, with a quick-drying jersey knit lining, and a soft nylon toe post. Compression molded EVA midsole wrapped in antiqued full-grain leather with hand-sewn stitching provides anatomically correct contour for a personlized fit and sustained comfort. Non-marking outsole with island inspired traction pods for enhanced grip and flexibility. Embroidered logos and perimeter stitching on the footbed, hand-sewn whip stitching and triangular laser detail on the straps. Imported.

NOTE: This item is excluded from promotional discounts.

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)

4.45

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Item 191133
$70.00
Kipi Water Resistant Thongs from OluKai®: "Kipi" equals "Rebel" in Hawaiian. These water-ready thongs feature water-resistant synthetic straps with quick-drying jersey knit lining and a soft, comfortable nylon toe post. Compression molded EVA midsole with brushed drop-in footbed for an anatomical fit and sustained comfort. Non-marking "Wet Grip Rubber" outsole with traction bottoms for land and wet surfaces. Tested and approved by the HLA (Hawaiian Lifeguard Association), with decorative strap stitching, welded hook logo, laser footbed detail, and a custom jacquard webbing tag, which represents the traditional colors of the HLA. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191129
$150.00
Hoe Perforated Leather Thongs from OluKai®: "Hoe" (HOY) is Hawaiian for "Paddle." High-quality, antiqued full-grain leather upper with octopus inspired strap perforations, and a soft, hand-sewn leather toe post. Compression molded EVA midsole wrapped in antiqued full-grain leather with hand-sewn stitching provides anatomically correct contour for a personlized fit and sustained comfort. Leather wrapped outsole with non-marking rubber traction pods infused with coconut fiber, and feather kappa texture for enhanced grip and flexibility. Imported.

NOTE: This item is excluded from promotional discounts.
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 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.

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Item 191101
$175.00
5.05

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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).

5.05

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Item 190849
$335.00
$300.50
Save 10%
5.05

(1)

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.
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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 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 191148
$115.00
4.05

(1)

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.
4.05

(1)

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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 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)

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Item 191200
$335.00
$199.00
Save 41%

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 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 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)

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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.

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(3)

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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.

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(1)

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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)

5.05

(1)

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 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 191102
$110.00
$69.00
Save 37%

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 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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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 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)

Item 191125
$85.00
5.05

(1)

Nohea Lole Canvas Slip Ons from OluKai®: Midweight washed cotton canvas upper with soft, moisture-wicking lining. Dual-density anatomical PU footbed with gel insert and soft microfiber cover – removable and washable. All-weather, non-marking rubber outsole pods for flexibility and traction. Patented Drop-In Heel® to wear as a sneaker or a slide. Hand-sewn seam stitching, elastic gore for a customized fit. Imported.

NOTE: This item is excluded from promotional discounts.
5.05

(1)

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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 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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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 191106
$120.00
Premium full-grain leather straps with decorative stitching inspired by traditional canoe rope lashing. Soft, microfiber lining. Compression-molded EVA midsole wrapped in full-grain leather. Anatomically correct contour for a personalized fit and sustained comfort over time. Full-grain, leather-wrapped outsole with non-marking, molded rubber traction pods. Hand-sewn leather toe post, octopus inspired laser-etched artwork on the footbed. Imported. Whole sizes: 8-13.

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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