Shoes & Boots

Sort By
Item 191135
$150.00
Teva's iconic modern outdoor sneaker is updated to deliver more versatility and improved performance. Waterproof leather upper keeps your feet dry. Lightweight, breathable mesh lining keeps your feet cool and comfortable. EVA foam footbed for cushioned support. FloatLite® midsole is super durable and feather light. Rubber outsole pods for superior traction. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191116
$75.00
4.75

(3)

Ember Moc Shoes from Teva®: Make your feet three times happier with this shoe that's also a sneaker and slipper as well. The adventure-ready ripstop upper features quilting details with polyester and suede overlays. Ribbed knit collar makes them extra cozy and the contrast webbing detail gives them a sportier look. The heels collapse so you can wear them as slides, too. Responsive PU footbed cushions the foot and puts a spring in your step. EVA-foam midsole for lightweight cushioning. Rubber outsole. Imported.

NOTE: This item is excluded from promotional discounts.

4.75

(3)

4.75

(3)

Item 191142
$195.00
Alex Shearling Lined Leather Sneakers from Trask™: Distressed leather uppers feature a rich, lived-in patina right out of the box. Fully lined in plush, top grade shearling. Slip-on styling with side gores for easy on and off. Rubber traction soles. Imported.

NOTE: This item is excluded from promotional discounts.

Item 191140
$95.00
High quality Italian distressed suede upper accented with handsome tonal stitching. Microfiber lining. Handmade Opanka construction: midsole is handsewn to the suede upper, giving the clog great flexibility and comfort. Removable footbed. Rubber outsole. 1.25” heel height. Wipe with a damp cloth to clean. Imported.
Item 191136
$130.00
5.05

(1)

Waterproof leather upper with knit-style, super light engineered mesh lining to keep your feet comfortable and dry. EVA foam footbed cushions your foot and softly supports it for all-day comfort. Float-Lite™ midsole is durable and feather light. Individual rubber outsole pods are strategically placed for superior traction. Responsive PU sockliner cushions the foot and puts a spring in your step. Imported.

NOTE: This item is excluded from promotional discounts.
5.05

(1)

5.05

(1)

Item 191138
$120.00
The perfect sneaker for criss-crossing your favorite island, named Kahu ’Eono, which means “Honored Guest.” With smooth, premium, full-grain leather upper, lined with a cooling and moisture-wicking fabric. Dual-density anatomical PU footbed with gel insert and a soft microfiber footbed printed with a sea life motif – footbed is removable and washable. Non-marking all-weather rubber outsole with decorative sidewall stitching. Patented Drop-In Heel® so you can wear it as a sneaker or a slide. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191216
$298.00
Burnished leather uppers give these boots a lived-in, rugged appearance. Leather lining. Leather outsoles. Made in Mexico.

NOTE: This item is excluded from promotional discounts.
Item 191215
$98.00
The California Special was originally a limited edition Mustang offered exclusively to California residents. The SeaVees California Special is a lace-to-toe mid-cut in tribute to the classic car – equally timeless and effortlessly cool. With suede uppers, custom contoured comfort footbeds, long-lasting calendar outsoles, soft, breathable cotton canvas linings, and signature flat eyelets. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191202
$165.00
Kualono Waterproof Leather Boots from OluKai®: 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, wrapped in high-abrasion TecTuff® synthetic leather. Heel pull loop for easy on and off. Imported.

NOTE: This item is excluded from promotional discounts.

Item 191210
$250.00
Fugitive GTX Water Resistant Boots from Asolo®: Enjoy all-day comfort and support on your next adventure with these amazing hiking boots. Water-resistant split-grain leather and Cordura® nylon uppers are lightweight, breathable and durable. GORE-TEX® liners are waterproof, yet breathable, for comfort in a variety of conditions. Reinforced rubber heels and toe boxes provide durable protection. DuoAsoflex midsoles mix a shock-absorbing soft layer with a stiffer shank for torsion control. Outsoles are a combination of polyurethane midsoles over a bi-density rubber bottom for cushioning and traction. Imported.
Item 191217
$495.00
This amazing burnished leather boot boasts a unique stitch design spanning the front and back quarter, while keeping the vamp unadorned to allow the beautiful, marbled goat leather to shine. Single stitch welt construction. Leather sole. Handmade in Texas.
Item 191214
$320.00
The all-terrain vehicle of hiking boots. One-piece water-resistant full-grain leather uppers. GORE-TEX® liners are waterproof, yet breathable, for comfort in a variety of conditions. Asolo/Vibram® highly technical soles. The outsole incorporates three shock absorbers that correspond with the areas of the foot that receive highest impact during activity. These shock absorbers can be identified by their different colors on the sole, and are created by combining two polyurethane layers – one of high and one of low density. Vibram molded rubber outsole, with the balance of the outsole featuring self-cleaning lugs designed for optimum performance on varying types of terrain. Imported.
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 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 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)

4.05

(1)

Item 191114
$95.00
$69.00 - $76.00
Save up to 27%
4.05

(2)

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.
4.05

(2)

4.05

(2)

Item 666502
$130.00
Makia Ulana Slip-On Shoe by Olukai®: Lightweight, breathable and ultra-comfortable mesh slip-on shoe features full-grain leather accents, a cushioned footbed and non-slip EVA outsole. Olukai's versatile Drop-In Heel® allows you to convert from a shoe to a slide instantly. Mesh upper. Full-grain leather accents. Rubber outsole. Imported.
NOTE: This item is excluded from promotional discounts.

Item 191132
$125.00
Terra Float Active Lace Up Sneakers from Teva®: This ultralight hybrid sneaker-sandal features a supportive laced upper in waterproof nubuck leather and neoprene, and Teva's innovative FloatLite™ foam construction that's both super light and supremely comfortable. Easy-cleaning Quick-lace for easy adjustability on the fly. Floatlite™ topsole and midsole supplies exceptional cushioned comfort. Durable Vibram® MegaGrip rubber outsole. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191118
$150.00
Arrowood Waterproof Hiker Shoes from Teva®: These cool, easy-wearing hikers feature the eVent premium waterproof-breathable membrane to keep your feet cool and dry. Rubberized toe cap provides rugged durability and toe protection. Responsive PU footbed cushions the foot and puts a spring in your step. Floatlite™ EVA-foam midsole with PU high-rebound heel pad for lightweight cushioning. Durable Vibram® rubber outsole stands up to the demands of rugged terrain. Nylon shank stabilizes and supports your foot on uneven terrain. Imported.

NOTE: This item is excluded from promotional discounts.
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 191126
$80.00
Original Universal Premier River Sandals from Teva®: Super comfortable and durable for outdoor activities, especially in hot weather. Polyester webbing upper dries quickly after getting wet. Universal Strapping System with easy hook-and-loop closure ensures a perfect fit. Responsive FloatLite® footbed cushions the foot and puts a spring in your step. Rubber outsole. Traction bottom. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191209
$295.00
Ike Tall Waxed Suede Boots from Trask™: Waxed suede uppers feature burnished leather trim at the cap toe and heel for a rugged appearance. Leather lining. Vibram® rubber outsole. 1" heel. Use buffalo butter to clean. 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 191207
$200.00
$150.00
Save 25%
Caceres Leather Captoe Boots from Pikolinos®: A handsome lace-up boot with a side zipper for easier on and off. 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 191146
$78.00
SeaVees pioneered the coastal California lifestyle with the introduction of this style in June 1964. Cordies are Inspired by the nostalgia of college campuses during the autumn and summer days spent in old-school corduroy board shorts. Featuring soft and durable, garment-dyed cotton corduroy uppers. Perforated custom contoured footbeds provide cooling comfort, and signature herringbone rubber outsoles offer maximum slip resistance. Imported.

NOTE: This item is excluded from promotional discounts.
Item 191120
$180.00
$135.00
Save 25%
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 191101
$175.00
$140.00
Save 20%
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).

5.05

(1)

5.05

(1)

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 191213
$225.00
Slade Basketweave Leather Loafers from Trask™: These handsome loafers feature a woven, dip-dyed buffalo calfskin upper with genuine handsewn construction. Leather lining and sock. Foam-cushioned insole. Buffed leather outsole with rubber insets for traction. Stacked leather heel with half rubber toplift. Imported.

NOTE: This item is excluded from promotional discounts.
Item 190470
$75.00
$60.00
Save 20%
4.45

(19)

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

(19)

4.45

(19)

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 190519
$375.00
$300.00
Save 20%
5.05

(5)

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

(5)

5.05

(5)

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 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 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 191200
$335.00
$251.50 - $268.00
Save up to 25%

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.

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.

  • Refine by:
  • Clear
    Type
    • Shoes
    • Boots
    • Sandals
    • Moccasins
    • Oxfords
    • Sneakers & Athletic
    • Slippers
    • Loafers
  • Clear
    Style
    • Lace-Up
    • Slip-On
    • Leather
    • High-Top
    • Low-Top
    • Chukka
    • Pull-On
  • Clear
    Size
    07
    07.5
    08
    08.5
    09
    09.5
    10
    10.5
    11
    11.5
    12
    13
    41
    42
    43
    44
    45
    46
    7
    7.5
    8
    8.5
    9
    9.5
  • Clear
    Size Range
    • Regular
  • Clear
    Color
    BROWN
    BLACK
    RED
    GREY
    GREEN
    NEUTRAL
    WHITE
    BLUE
  • 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