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Shirts for Grandfathers

Find shirts for grandfathers with classic style, whether you’re picking out a gift for Grandpa or helping him refresh his wardrobe. Start with the looks he already enjoys, then compare available styles, fit descriptions and sizing details to help narrow your choice.

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Men's Scotch Plaid Flannel Shirt, Traditional Fit
L.L.Bean Men's Scotch Plaid Flannel Shirt, Traditional Fit
A soft, traditional-fit flannel shirt in authentic grey Stewart tartan, made from high-quality Portuguese cotton.
(20,377)
$59.95 $59.95
SALE
What customers like:
Well-made
Versatile style
Softness
Warmth
Comfortable fit
$59.95 $59.95
SALE
Men's Carefree Unshrinkable Tee, Traditional Fit Short Sleeve
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit Short Sleeve
A gray heather, traditional fit, short-sleeve tee made from soft, wrinkle-resistant, 100% jersey-knit cotton.
(12,867)
$26.95 $26.95
SALE
What customers like:
Washes well
High quality
Wrinkle-free
Durable fabric
Comfortable fit
$26.95 $26.95
SALE
Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve
A resilient charcoal heather long-sleeve tee made of 100% cotton that resists wrinkles and shrinking.
(10,664)
$36.95 $36.95
SALE
What customers like:
No shrinkage
Durable
High-quality fabric
Good color accuracy
Comfortable fit
$36.95 $36.95
SALE
Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth
L.L.Bean Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth
A charcoal heather flannel shirt with sheepskin shearling lining, offering softness, warmth, and wrinkle resistance.
(8,393)
$79.95 $79.95
SALE
What customers like:
Great fit
High quality
Softness
Warmth
Comfortable
$79.95 $79.95
SALE
Men's Premium Double L® Polo, Banded Short-Sleeve Without Pocket
L.L.Bean Men's Premium Double L® Polo, Banded Short-Sleeve Without Pocket
A super-soft, all-cotton white polo that resists wrinkles, fading, shrinking, and pilling.
(8,093)
$44.95 $44.95
SALE
What customers like:
High quality
Perfect fit
Durable fabric
Softness
Comfortable fit
$44.95 $44.95
SALE
Men's Chamois Shirt, Traditional Fit, Plaid
L.L.Bean Men's Chamois Shirt, Traditional Fit, Plaid
A gray plaid flannel shirt crafted from heavyweight Portuguese cotton for exceptional warmth and softness.
(7,285)
$84.95 $84.95
SALE
What customers like:
Warm and substantial heavyweight fabric
High quality and durable construction
Attractive colors and patterns
Exceptionally soft and comfortable
True to size with a good fit
$84.95 $84.95
SALE
Men's Chamois Shirt, Traditional Fit
L.L.Bean Men's Chamois Shirt, Traditional Fit
A heavy-weight charcoal gray heather flannel shirt made from 7.5 oz. Portuguese cotton for exceptional softness.
(7,136)
$79.95 $79.95
SALE
What customers like:
Exceptional softness
High quality
Perfect fit
Comfortable wear
Great warmth
$79.95 $79.95
SALE
Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit
L.L.Bean Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit
A resilient gray heather tee made of 100% cotton that resists wrinkles, shrinking, fading, and pilling.
(7,068)
$26.95 $26.95
SALE
What customers like:
Good quality
True to size fit
Durable
Color retention
Comfortable
$26.95 $26.95
SALE
Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve Henley
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve Henley
A gray heather long-sleeve henley made of 100% cotton that resists shrinking, fading, and pilling.
(6,468)
$44.95 $44.95
SALE
What customers like:
Great fit
High quality
Versatile
Comfortable
Soft fabric
$44.95 $44.95
SALE
Men's Scotch Plaid Flannel Shirt, Slightly Fitted
L.L.Bean Men's Scotch Plaid Flannel Shirt, Slightly Fitted
A slightly fitted, 100% Portuguese cotton flannel shirt in authentic grey Stewart tartan with a button-down collar.
(6,433)
$59.95 $59.95
SALE
What customers like:
Quality construction
Perfect fit
Softness
Warmth
Vibrant colors
$59.95 $59.95
SALE
Men's Two-Layer River Driver's Shirt®, Traditional Fit Henley
L.L.Bean Men's Two-Layer River Driver's Shirt®, Traditional Fit Henley
A classic bright navy heather Henley with a wool blend outer layer and soft cotton inner layer.
(6,147)
$79.95 $79.95
SALE
What customers like:
Versatile and stylish
Beautiful color options
High quality and durability
Warmth and coziness
Comfortable fit
$79.95 $79.95
SALE
Men's Sunwashed Canvas Shirt, Traditional Fit
L.L.Bean Men's Sunwashed Canvas Shirt, Traditional Fit
A prewashed, 100% cotton canvas shirt in bay leaf with a relaxed fit and durable double-needle stitching.
(5,386)
$69.95 $69.95
SALE
What customers like:
Durable
Comfortable
Good fit
Nice color
Well made
$69.95 $69.95
SALE
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
L.L.Bean Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
A wrinkle-free, 100% cotton poplin shirt in nautical blue check, featuring moisture-wicking TrueCool® fabric.
(4,814)
$69.95 $69.95
SALE
What customers like:
Perfect fit
Wrinkle-free
Durable
Comfortable
Beautiful colors
$69.95 $69.95
SALE
Men's Unshrinkable Mini-Waffle Henley, Long-Sleeve Traditional Fit
L.L.Bean Men's Unshrinkable Mini-Waffle Henley, Long-Sleeve Traditional Fit
A 100% cotton, shale gray heather henley that resists shrinking, fading, and pilling.
(4,807)
$69.95 $69.95
SALE
What customers like:
Fits well
Good quality
Warmth
Comfortable
Soft fabric
$69.95 $69.95
SALE
Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit, Long-Sleeve
L.L.Bean Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit, Long-Sleeve
A gray heather long-sleeve tee made of soft, wrinkle-resistant cotton with a comfortable traditional fit.
(3,527)
$36.95 $36.95
SALE
What customers like:
Easy care
Perfect fit
Durable
Good quality material
Comfortable
$36.95 $36.95
SALE
Men's Carefree Unshrinkable Tee, Traditional Fit, Henley
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit, Henley
A soft, gray heather henley that resists shrinking, fading, and pilling, made from 100% jersey-knit cotton.
(3,027)
$32.95 $32.95
SALE
What customers like:
Soft material
Good quality
True to size
Durable
Comfortable
$32.95 $32.95
SALE
Men's Premium Double L® Polo, Hemmed Short-Sleeve with Pocket
L.L.Bean Men's Premium Double L® Polo, Hemmed Short-Sleeve with Pocket
A supersoft, juniper cotton polo that resists wrinkles, fading, shrinking, and pilling with a no-roll collar.
(2,956)
$44.95 $44.95
SALE
What customers like:
Great fit
High quality
Good color options
Durable
Comfortable
$44.95 $44.95
SALE
Men's Carefree Unshrinkable Mockneck Shirt
L.L.Bean Men's Carefree Unshrinkable Mockneck Shirt
A charcoal heather mockneck shirt made of 100% cotton that resists shrinking, fading, and wrinkling.
(2,952)
$44.95 $44.95
SALE
What customers like:
Perfect fit
Excellent quality
Durability
Comfortable
Good style
$44.95 $44.95
SALE
Men's Sherpa-Lined Scotch Plaid Shirt, Slightly Fitted
L.L.Bean Men's Sherpa-Lined Scotch Plaid Shirt, Slightly Fitted
A slightly fitted, ultrawarm grey Stewart plaid shirt with soft Sherpa fleece lining and taffeta-lined sleeves.
(2,758)
$130 $130
SALE
What customers like:
Attractive design
Exceptional warmth
Soft and cozy feel
High quality construction
Comfortable fit
$130 $130
SALE
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check
L.L.Bean 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.
(2,628)
$59.95 $49.99
SALE
What customers like:
Great fit and true to size
Attractive colors and stylish appearance
Wrinkle-free and easy care
Comfortable and soft fabric
Durable and well constructed
$59.95 $49.99
SALE
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit
L.L.Bean Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit
A wrinkle-free, 100% cotton oxford shirt in white, offering a relaxed traditional fit and durable buttons.
(2,511)
$79.95 $79.95
SALE
What customers like:
High quality
Perfect fit
Wrinkle-free
Durable
Versatile
$79.95 $79.95
SALE
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
L.L.Bean Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
A bright blue, wrinkle-free cotton shirt with a traditional fit and ultrasmooth finish for all-day comfort.
(2,091)
$79.95 $67.99
SALE
What customers like:
Consistent sizing
Durable construction
Wrinkle-free quality
High-quality materials
Comfortable fit
$79.95 $67.99
SALE
Men's Tropics Shirt, Short-Sleeve Print
L.L.Bean Men's Tropics Shirt, Short-Sleeve Print
A breathable green cotton shirt with a relaxed fit and weathered print for hot days.
(2,027)
$54.95 $54.95
SALE
What customers like:
Great color and pattern
Durable quality
Versatile style
Cool and lightweight
Comfortable fit
$54.95 $54.95
SALE
Men's Scotch Plaid Flannel Shirt, Slim Fit
L.L.Bean Men's Scotch Plaid Flannel Shirt, Slim Fit
A slim-fit grey Stewart flannel shirt made from high-quality Portuguese cotton, featuring authentic Scottish tartans.
(1,791)
$59.95 $59.95
SALE
What customers like:
Perfect fit
Soft and comfortable
Stylish design
High-quality cotton
Warm and durable
$59.95 $59.95
SALE

Shirts for Grandfathers

Finding a shirt for your grandfather starts with knowing his style, not dressing him for his age. Our Shirts for Grandfathers selection is a place to explore choices with his individual tastes in mind, whether he gravitates toward familiar checks, understated solids or a little more color. Think of the details you recognize from years of family photographs: the collar he always leaves open, the sleeves he prefers long or short, the shade he reaches for again and again. Those familiar preferences can tell you more than a passing trend ever could. A shirt doesn’t have to be a departure from his usual wardrobe to feel like a thoughtful addition. Sometimes the best choice is close to an old favorite, with a different pattern or a color that works alongside what he already owns.

When comparing shirts, give size and shape as much attention as color. A size label is a starting point, but the measurements and fit descriptions on each item offer a clearer picture of how it will fit. If you’re buying a gift, checking the size of a shirt he currently wears is helpful; comparing its measurements with the listed size information is better still. Notice whether he prefers a closer or roomier silhouette, a button-down collar or a simpler neckline, and a hem he can tuck in or leave out according to the item’s design. Small details deserve a look, too. A chest pocket may be part of his usual style, while another grandfather might prefer a cleaner front. Read the individual care instructions before choosing, especially if he has an established laundry routine he likes to keep simple.

Shirts can make personal gifts for birthdays, Father’s Day or a family celebration without requiring a grand gesture. From grandchildren choosing their first gift to adult children who know his wardrobe well, the thought comes through in the particulars. Perhaps the color recalls the shirt he wore in a favorite family portrait, or the pattern resembles one he has enjoyed for years. Let that connection guide the choice without assuming every grandfather shares the same taste. Some welcome something different; others know exactly what they like. If you’re shopping for yourself, that same approach holds true: start with your own preferences and choose something that feels like you. Timeless style leaves plenty of room for personality, and the right shirt should reflect the person rather than the occasion on the gift tag.

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