Winter Outfitting

Cold weather, warm moments. Discover effortless outfitting for the season ahead, from soft flannels to versatile knits, built for comfort, travel, and time spent with the people you love.

16 Items

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Man wearing a navy blue flannel shirt with chest pockets and button front closure.
Navy blue flannel shirt with button front, collar, and two chest pockets with flaps.
Man wearing a navy blue flannel shirt with long sleeves and a collar, shown from the back.
Man wearing a navy blue flannel shirt with button front, collar, and chest pockets.
Man wearing a navy blue flannel shirt with chest pockets over a white undershirt and beige pants.
Navy twill fabric with diagonal ribbed texture and natural folds throughout the material.
Man wearing navy twill flannel shirt over white t-shirt with khaki pants in outdoor field.
Man wearing a navy button-front flannel shirt over a white t-shirt and tan pants standing in a field.

Dunewood Flannel

$148
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Man wearing khaki five-pocket pants with a patterned belt and casual sneakers.
Khaki five-pocket pants with a flat front, button closure, and straight leg silhouette.
Man wearing khaki five-pocket pants with back pockets visible and woven belt detail.
Man wearing khaki five-pocket pants with a braided leather belt and pink shirt.
Man wearing a coral polo shirt and khaki five-pocket pants with a brown belt.
Close-up of khaki cotton twill fabric showing diagonal weave pattern and soft texture.
Man wearing khaki five-pocket pants and gray shirt leaning against blue vintage truck.
Man wearing khaki five-pocket pants with a gray button-up shirt and brown leather boots.

Horizon 5-Pocket Pant

$138
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Person wearing light blue jeans from Fair Harbor and white sneakers on a white background
A pair of men's straight-fit blue denim jeans with a 5-pocket design on a white background.
Man wearing light blue denim pants with faded wash and back pockets visible from behind.
Light blue wash denim pants with a relaxed fit displayed on a model wearing casual sneakers.
Man wearing light blue stretch denim pants with hand in front pocket and gray shirt visible.
Detail image of the waist band and pocket design of pair of blue denim pants.
Man wearing a blue-gray t-shirt and light blue beach wash denim pants with white sneakers.
Man wearing light blue stretch denim pants and a striped shirt leaning against a wooden railing outdoors.
Man wearing light wash denim pants with striped shirt standing outdoors near water.

Driftwood Stretch Denim Pant

$168
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Man wearing a light oak striped oxford shirt with a button-down collar and long sleeves.
Men's long-sleeve oxford shirt with vertical oak and white stripes and button closure.
Man wearing a long-sleeved oxford shirt with vertical tan and white stripes, shown from behind.
Man wearing a light tan and white striped Oxford shirt with white button closure and collar detail.
Man wearing a cream and beige vertical striped Oxford shirt with button front and chest pocket.
Close-up of white and oak striped oxford shirt fabric showing diagonal woven texture pattern.
Man wearing a light striped oxford shirt with rolled sleeves and blue jeans in a bar setting.

Salty Oxford Shirt

$80 $128
Man wearing deep sea wash denim pants with a white shirt and beige canvas shoes.
A pair of men's straight-fit blue denim jeans in the color Deep Sea Wash with a 5-pocket design on a white background.
Man wearing dark blue denim pants with back pockets, shown from behind with white shirt and canvas shoes.
Man wearing dark blue denim pants with copper rivets and beige canvas sneakers.
Close up of person wearing driftwood denim in deep sea wash pulling on the side seam of jeans to show the stretch of the jeans.
Detail image of the waist band and pocket design of pair of blue denim pants.
Man wearing light blue stretch denim pants and a striped shirt leaning against a wooden railing outdoors.
Man wearing light wash denim pants with striped shirt standing outdoors near water.

Driftwood Stretch Denim Pant

$168
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Man wearing black wash denim pants with a gray sweater and brown suede shoes.
Black wash denim pants with a straight leg, five-pocket design, and copper-toned hardware details.
Person wearing black wash denim pants with visible back pockets and a gray sweater.
Man wearing black wash denim pants with gray ribbed sweater, hands in pockets.
Man wearing a gray long-sleeve shirt and black wash denim pants with brown shoes.
Black wash denim pants with copper button hardware and visible stitch detailing on front pockets.
Man wearing black wash denim pants with a tan shirt standing in front of an open vehicle.
Person wearing black wash denim pants with a tan shirt and brown boots by a truck.

Driftwood Stretch Denim Pant

$168
Light blue jeans from Fair Harbor worn by a person on a white background
Light wash straight fit denim pants with a 5-pocket silhouette on a white background.
Light blue jeans worn by a person on a white background
Person wearing light wash denim pants with a straight leg and cream canvas shoes.
Man wearing light wash denim pants with a gray shirt, showing front pocket and waistband detail.
Detail image of the waist band and pocket design of pair of blue denim pants.
Man wearing light wash denim pants and charcoal gray t-shirt standing against white background.
Man wearing light wash denim pants with striped shirt standing outdoors near water.
Man wearing light blue stretch denim pants and a striped shirt leaning against a wooden railing outdoors.

Driftwood Stretch Denim Pant

$168
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Man wearing a heather grey hoodie with drawstring and long sleeves over navy pants.
Heather grey hoodie with drawstring and ribbed cuffs displayed against a white background.
Man wearing a heather grey hoodie with long sleeves and a drawstring hood, shown from the back.
Man wearing a heather grey hoodie with drawstring and ribbed texture detail visible.
Man wearing heather grey hoodie with drawstring and navy blue pants standing against white background.
Close up of grey tailwind fabric
Man wearing a cream-colored hoodie with drawstrings, pulling the hood over his head outdoors.
Man wearing a cream-colored hoodie and blue jeans crouching in a harvested field.

Tailwind Hoodie

$108
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Man wearing navy five-pocket pants with a white t-shirt and tan boat shoes.
Navy five-pocket pants with a flat front and button closure displayed on a white background.
Man wearing navy blue five-pocket pants with back pockets visible from behind.
Man wearing navy five-pocket pants with white shirt, showing front pocket detail and fit.
Man wearing a white short-sleeve t-shirt and navy blue five-pocket pants with brown shoes.
Close-up of navy blue woven fabric with a diagonal twill texture and subtle sheen.
Man wearing navy five-pocket pants and light blue shirt leaning against blue pickup truck bed.
Navy five-pocket pants worn with a brown leather belt, showing front pocket and waistband detail.
Man wearing navy five-pocket jeans with brown belt and tan boots outdoors.

Horizon 5-Pocket Pant

$138
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Man wearing black five-pocket pants with white t-shirt and gray canvas sneakers.
Black five-pocket pants with a straight leg and metal button waistband closure.
Man wearing black five-pocket pants with white shirt, viewed from back.
Black five-pocket pants with a button fly and brass hardware detail on the waistband.
Man wearing a white t-shirt and black five-pocket pants styled with gray sneakers.
Black pants fabric with diagonal seams and a smooth woven texture under natural lighting.
Man wearing navy five-pocket pants and light blue shirt leaning against blue pickup truck bed.
Man wearing navy five-pocket jeans with brown belt and tan boots outdoors.
Navy five-pocket pants worn with a brown leather belt, showing front pocket and waistband detail.

Horizon 5-Pocket Pant

$138
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Man wearing black shorts with cream drawstring waist and gray canvas sneakers.
Black shorts with an elastic waistband and cream-colored drawstring closure against a light background.
Man wearing black shorts with an elastic waistband and back pocket, paired with a white tank top.
Black shorts with Fair Harbor brand label and back pocket detail visible.
Man wearing black shorts with gray liner shorts and a cream drawstring, paired with gray canvas sneakers.
Man wearing a white crew-neck t-shirt and black shorts standing against a white background.
Close-up of black fabric with diagonal folds and textured weave pattern throughout.
Man standing on patio wearing navy one short and tshirt, with drink in hand. Colorful table and chairs behind him.

One Short

$78
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Man wearing a white crew neck t-shirt with short sleeves and dark blue shorts.
White saltaire t-shirt on a white background
Man wearing a white short-sleeve t-shirt, shown from behind against a plain white background.
Man wearing a white short-sleeved crew neck t-shirt against a neutral background.
Man wearing a white short-sleeve t-shirt with a small woven label on the side seam.
Man wearing white short-sleeve crew neck t-shirt with navy shorts and tan boat shoes.
Man wearing a blue saltaire t-shirt and bayberry trunks standing in front of a colorful boat.

Saltaire Tee

$58
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Man wearing a blue-gray short-sleeved crewneck t-shirt paired with light blue jeans.
Navy blue saltaire t-shirt on a white background
Man wearing a navy blue short-sleeved crew neck t-shirt, shown from behind.
Man wearing a navy blue crewneck short-sleeve t-shirt against a white background.
Navy crew neck t-shirt worn with blue jeans, showing side seam and small brand label detail.
Man wearing a navy blue short-sleeved crewneck tee with light blue jeans and dark sneakers.
Man wearing a blue saltaire t-shirt and bayberry trunks standing in front of a colorful boat.
Close up of fabrics for person wearing a blue saltaire t-shirt and bayberry trunks standing in front of a colorful boat.

Saltaire Tee

$58
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Man wearing khaki shorts with a drawstring waistband and tan sandals.
Khaki one shorts in 8 inch inseam with a drawstring on a white background
Man wearing khaki shorts with elastic waistband and back pocket label, paired with blue shirt.
Khaki shorts with an elastic waistband and back pocket, worn with a blue shirt.
Man wearing light blue t-shirt and khaki shorts with tan sandals against white background.
Man wearing a gray t-shirt and black shorts standing outdoors on pavement.

One Short

$78
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Person wearing a pair of blue 8 inch one shorts with a drawstring on a white background. Paired with a tshirt and white sneakers.
Navy 8 inch one shorts with a drawstring on a white background
Person wearing a pair of navy 8 inch one shorts with a drawstring on a white background. Showing the liner underneath.
Person wearing a pair of navy 8 inch one shorts with a drawstring on a white background. Showing the side view.
Man standing on patio wearing navy one short and tshirt, with drink in hand. Colorful table and chairs behind him.

One Short

$78
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Person wearing gray shorts with a white drawstring on a white background
Grey shorts with an elastic waistband and white drawstring closure displayed against a plain background.
Man wearing grey shorts with an elastic waistband viewed from behind.
Gray shorts with elastic waistband and Fair Harbor brand label on back pocket.
Man wearing grey shorts with cream drawstring and white and grey undershorts visible.
Man wearing a white short-sleeve t-shirt and grey shorts with canvas sneakers.
Grey woven fabric with diagonal folds and a textured, matte surface finish.
Man standing on patio wearing navy one short and tshirt, with drink in hand. Colorful table and chairs behind him.

One Short

$78
+3 more
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