Relaxed Winter Shirts
Relaxed winter shirts are a go-to choice for keeping comfortable and enjoying the season to its fullest. Perfect for layering or wearing on their own, these shirts offer a timeless look and an easygoing feel that suits everything from outdoor adventures to cozy days indoors. With versatile styles designed to keep up with winter’s demands, it’s simple to find options that fit right into your cold-weather wardrobe. Whether you’re heading out for a walk or settling in by the fire, relaxed winter shirts make it easy to stay warm and comfortable all season long.
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Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
A deep green, 100% cotton, wrinkle-free sport shirt with moisture-wicking TrueCool® fabric and a relaxed fit.
Pros: High quality Wrinkle-free Lightweight Good fit Comfortable
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Men's Chamois Shirt, Slightly Fitted, Plaid
A slightly fitted, forest shade chamois shirt made from 7.5 oz. Portuguese cotton flannel for exceptional warmth.
Pros: Perfect fit Exceptional warmth Comfortable wear Excellent quality Versatile use
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Men's Chamois Shirt, Slightly Fitted
A brown, slightly fitted shirt crafted from thick Portuguese cotton flannel for exceptional warmth and softness.
Pros: Flattering fitted shape Soft and comfortable Warm and heavy weight Rich color and nice fabric Durable and well constructed
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Men's Maine Guide Shirt with PrimaLoft
A warm PrimaLoft wool blend shirt in cream and black check, ideal for layering and outdoor activities.
Pros: Great fit Excellent quality Warm and comfortable Durable material Stylish appearance
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Men's Maine Guide Shirt
A durable, 85% wool and 15% nylon plaid shirt, perfect for layering, in cream and black.
Pros: Great fit High quality Good quality Cushioning Warm
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Men's Katahdin Performance Flannel Shirt-Jacket, Hi-Pile Fleece-Lined Plaid
A multi-color wool blend flannel shirt-jacket featuring ultrasoft hi-pile fleece lining and insulated sleeves.
Pros: Soft and comfortable Fits as expected High quality and durable Attractive colors and appearance Warmth stands out
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Men's Maine Guide Zip-Front Jac-Shirt
A versatile wool/nylon jac-shirt with a relaxed fit, ideal for layering or wearing solo year-round.
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Women's Wrinkle-Free Pinpoint Oxford Shirt, Relaxed Fit Long-Sleeve Print
A relaxed-fit green cotton shirt featuring fun prints and a wrinkle-free, easy-care finish.
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Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check
A red check short-sleeve shirt made from wrinkle-free, moisture-wicking cotton poplin for lasting comfort.
Pros: Great fit and true to size Attractive colors and stylish appearance Wrinkle-free and easy care Comfortable and soft fabric Durable and well constructed
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Women's Wrinkle-Free Pinpoint Oxford Shirt, Long-Sleeve Relaxed Fit
A relaxed fit, wrinkle-free white oxford shirt made from 100% cotton with pearlized buttons.
Pros: Crisp appearance High quality Perfect fit Wrinkle-free Versatile
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Women's Vacationland Seersucker Shirt, Long-Sleeve
A relaxed-fit, white cotton seersucker shirt with chest pockets and a slightly longer length for great coverage.
Pros: Lightweight and breathable Easy to care for Versatile style Attractive design and colors Comfortable fit
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Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
A deep green, slightly fitted check shirt made from 100% wrinkle-free cotton poplin with moisture-wicking TrueCool® fabric.
Pros: Attractive color High-quality construction Wrinkle-free fabric Comfortable fit No ironing needed
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Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
A vintage indigo, wrinkle-free, 100% brushed cotton shirt with a slightly fitted untucked fit.
Pros: Great fit Attractive appearance Wrinkle-free Comfortable brushed cotton Beautiful color
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Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
A breathable blue plaid chambray shirt in a cotton blend with stretch and moisture-wicking comfort.
Pros: Wrinkle-free material High quality construction Durable and sturdy fabric Attractive untucked style Comfortable fit
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Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve
A green cotton-blend chambray shirt with built-in stretch and a relaxed untucked fit.
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Men's Bean's Heritage Soft Cotton Fisherman Sweater, Button-Mock
A richly textured, cream cable-knit sweater with a three-button mock neck, made from 100% organic cotton.
Pros: Provides warmth Receives compliments Versatile with different outfits Stylish appearance Comfortable fit
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Women's Comfort Corduroy Relaxed Shirt, Zip Hoodie
A relaxed-fit, larkspur corduroy zip-hoodie with side pockets and adjustable drawstring hood.
Pros: Great fit High-quality material Stylish design Warm and cozy Beautiful color
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Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit
A white cotton blend oxford shirt with moisture-wicking and stretch, designed for untucked wear.
Pros: Quality fabric Versatile Good fit Dressy yet comfortable Casual style
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Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit
A light cobalt, slightly fitted oxford shirt with moisture-wicking cotton blend and stretch for comfort.
Pros: High material quality Well-made Cute print Great appearance Comfortable
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Men's Comfort Stretch® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
A green plaid chambray shirt in a breathable cotton blend with stretch and a modern untucked fit.
Pros: Attractive colors Perfect fit Receives compliments Great looking style
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Men's Tropicwear Shirt, Plaid Long-Sleeve
A dark amber plaid long-sleeve shirt with UPF 50+ protection, built-in stretch, and excellent venting.
Pros: High quality Effective sunblock Well-made Cool and comfortable fabric Good fit
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Men's Organic Cotton Waffle Sweater, Rollneck Crew, Stripe
A rugged green crewneck sweater crafted from 100% organic cotton with a thick waffle-knit texture.
Pros: Great fit Handsome appearance Ideal for cool weather Warm and cozy Comfortable to wear
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Men's Double L Field Shirt, Hunter Orange
A rugged, hunter orange field shirt made of durable cotton acrylic with reinforced forearms and bi-swing articulation.
Pros: Great fit Durable quality Warmth Perfect sleeve length Excellent cuff design
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Women's Maine Guide Zip Front Jac-Shirt with Primaloft
A loden wool-blend jac-shirt with PrimaLoft insulation, perfect for layering in cold weather.
Pros: Great fit High quality Non-itchy material Excellent warmth
