Casual Shirts For Older Men

Casual shirts for older men are thoughtfully designed to bring together comfort, timeless style, and everyday versatility. Whether relaxing at home, meeting friends for coffee, or heading out for a weekend adventure, these shirts make it easy to look and feel your best. With classic details and a range of easy-to-wear options, finding the right casual shirt is simple—so you can focus on enjoying every moment.

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264 Items

Men's BeanFlex® Twill Shirt, Traditional Untucked Fit, Long-Sleeve
Price was from: $64.95 now: $44.99

A rugged pale khaki twill shirt with built-in stretch, perfect for untucked wear and all-day comfort.

Pros: High quality Wrinkle-free Good color options Durable material Comfortable fit
Men's Scotch Plaid Flannel Shirt, Traditional Fit

A soft, traditional fit flannel shirt in blue Mackellar plaid, made from high-quality Portuguese cotton.

Pros: Perfect fit Well-made Warmth Versatile Soft and comfortable material
Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve

A navy blue, long-sleeve tee made of 100% cotton that resists shrinking, fading, and pilling.

Pros: Durable and well-made Variety of colors Maintains shape and color High-quality fabric Comfortable fit
Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth

A deep sapphire multi houndstooth flannel shirt offering superior softness, warmth, and resistance to shrinking.

Pros: Great quality Warmth Excellent fit Comfortable Superior softness
Men's Chamois Shirt, Traditional Fit

A deep green, heavy-weight Portuguese cotton flannel shirt, perfect as a shirt, light jacket, or essential layer.

Pros: Nice colors Great quality Warmth Versatile use Comfortable fit
Men's Sunwashed Canvas Shirt, Traditional Fit

A mist blue, 100% cotton canvas shirt with a relaxed fit and durable double-needle stitching.

Pros: Versatile for seasons High quality Durable construction Great color options Comfortable fit
Men's Premium Double L® Polo, Long-Sleeve Without Pocket

A green long-sleeve polo made from supersoft cotton that resists wrinkling, fading, shrinking, and pilling.

Pros: Warmth and insulation True to size Durable material Soft fabric Comfortable fit
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check

A red check button-down shirt made from wrinkle-free, moisture-wicking cotton poplin for lasting comfort.

Pros: Excellent fit and comfortable High quality and durable fabric Wrinkle-free and easy care Classic style and versatile design Attractive color and pattern options
Men's Fleece-Lined Flannel Shirt, Traditional Fit

A supersoft, fleece-lined flannel shirt in coal plaid, offering a relaxed fit and cozy warmth.

Pros: Quality Comfort Warmth Softness Versatility
Men's Carefree Unshrinkable Mockneck Shirt

A soft, white cotton mockneck shirt that resists shrinking, fading, wrinkling, and pilling.

Pros: Perfect fit Excellent quality Durability Versatile Comfortable
Men's Wicked Good Flannel Shirt, Slightly Fitted, Houndstooth

A slightly fitted charcoal heather flannel shirt offering superior softness, wrinkle resistance, and a single chest pocket.

Pros: High quality Perfect fit Comfortable wear Stylish design Superior softness
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve

A green cotton blend shirt with moisture-wicking stretch, perfect for untucked casual wear.

Pros: Great fit High quality Attractive color Versatile design Excellent comfort
Men's Carefree Unshrinkable Tee, Traditional Fit Short-Sleeve

A yellow, wrinkle-resistant cotton tee that maintains its shape and softness through countless washes.

Pros: Versatile and stylish Great color options High-quality construction Comfortable fit Softness and durability
Men's Chamois Shirt, Traditional Fit, Plaid

A heavyweight blue plaid flannel shirt crafted from ultra-soft, durable Portuguese cotton chamois fabric.

Pros: Attractive colors and patterns Exceptionally soft and comfortable Durable and high quality construction Warm and substantial fabric True to size with a good fit
Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit

A soft red cotton tee with a chest pocket, resisting wrinkles, shrinking, fading, and pilling.

Pros: Great fit and true to size Very comfortable Does not shrink or fade Durable and well made Soft and substantial fabric
Men's Premium Double L® Polo, Hemmed Short-Sleeve with Pocket

A deep wine, supersoft cotton polo that resists wrinkles, fading, shrinking, and pilling, with a no-roll collar.

Pros: Great fit High quality Good color selection Durable Comfortable
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check

A wrinkle-free blue check cotton shirt with moisture-wicking TrueCool® fabric and a relaxed traditional fit.

Pros: Great fit High quality Wrinkle-free Comfortable Nice color
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit

A wrinkle-free white cotton shirt with a traditional fit, offering a freshly pressed look without ironing.

Pros: High quality Perfect fit Wrinkle-free Professional look Versatile
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall

A wrinkle-free, 100% cotton shirt in crystal blue tattersall with a traditional, relaxed fit.

Pros: High quality Perfect fit Wrinkle-free Comfort Durability
Men's Tropics Shirt, Short-Sleeve Print
Price was from: $49.95 now: $39.99

A breathable, extra-soft brown cotton shirt with a relaxed fit and casual, weathered print.

Pros: Durable quality Versatile style Great for summer Soft fabric Comfortable fit
Men's Sunwashed Canvas Shirt, Traditional Fit Short-Sleeve

A soft, blue cotton canvas short-sleeve shirt with a relaxed fit and durable double-needle stitching.

Pros: Perfect fit Durable and sturdy Versatile style Comfortable to wear Soft fabric
Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
Price was from: $69.95 now: $44.99

A red check button-down shirt made from wrinkle-free, moisture-wicking cotton poplin for lasting comfort.

Pros: No ironing required Attractive color and style High-quality construction Wrinkle-free fabric Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print

A breathable blue cotton-blend chambray shirt with built-in stretch and a relaxed, untucked fit.

Pros: Soft and stretchy fabric True to size fit Versatile style Comfortable material High quality construction
Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $44.99

An arctic blue, wrinkle-free, ultrasoft brushed cotton shirt designed for a slightly fitted untucked look.

Pros: Great fit Attractive appearance Wrinkle-free Comfortable brushed cotton Beautiful color

Casual Shirts For Older Men

When it comes to building a versatile wardrobe, casual shirts for older men are a true cornerstone. Whether you’re heading out for a relaxed lunch with friends, enjoying a crisp autumn stroll, or simply unwinding at home, the right shirt can make all the difference in comfort and confidence. Many men over 50 find themselves reaching for shirts that blend timeless style with practical features—think soft, breathable fabrics like cotton or linen, subtle patterns, and classic solid colors such as navy, gray, or white. These shirts are designed to be easy to wear, with details like button-down collars, gentle tailoring, and relaxed fits that move with you throughout the day. The best shirts for older men often feature thoughtful touches: a chest pocket for reading glasses, a durable yet comfortable weave, and finishes that resist wrinkles so you can look put-together with minimal effort. For those who appreciate a little extra polish, options that can be worn tucked or untucked provide flexibility for any occasion, while polos and henleys add variety without sacrificing ease.

Older men casual wear is about more than just function—it’s about feeling at home in your clothes, no matter where the day takes you. Gifting an old man shirt is a thoughtful gesture, especially for birthdays, holidays, or just to show you care. A well-made casual shirt can become a favorite piece, offering lasting value and versatility season after season. As the weather cools in October, layering becomes key; casual shirts pair effortlessly with sweaters, vests, or light jackets, making them a smart choice for transitional weather. Subtle checks, gentle plaids, and understated stripes add a touch of personality without overwhelming the look. Many men appreciate age shirt styles that respect their need for comfort, easy care, and timeless appeal—qualities that never go out of style. Whether you’re shopping for yourself or searching for a gift, focusing on quality and durability ensures that these shirts will hold up to years of wear, making them a reliable part of any wardrobe.

When selecting shirts for men over 50, it’s helpful to consider how each piece will fit into daily routines and special moments alike. From casual get-togethers to family gatherings or even a relaxed weekend away, a good shirt should always feel right. Look for those with soft finishes, easy button closures, and ample room to move—features that make dressing simple and enjoyable. For more inspiration on timeless style and wardrobe essentials, explore our collection of Classic Clothing For Older Men, where you’ll find even more options designed to keep you comfortable and confident, whatever the season brings.

FAQs

The best fabrics for casual shirts for older men are typically soft, breathable materials like cotton, linen, and cotton-blend performance fabrics. These materials offer comfort, durability, and easy care, making them well-suited for everyday wear.

Solid colors such as navy, white, gray, and olive are especially versatile and easy to pair with other wardrobe staples. Subtle patterns like checks, stripes, or gentle plaids also add interest without overwhelming the look, making them great choices for men over 50.

Casual shirts can be dressed up with chinos or layered under a sweater for gatherings, or worn untucked with jeans for a relaxed weekend look. Rolling up the sleeves or pairing with a light jacket can also help transition your style through changing seasons.

Comfort features include soft, non-restrictive fabrics, easy-to-use button closures, relaxed tailoring, and thoughtful details like chest pockets. Shirts designed for easy movement and minimal maintenance are especially popular for older men.

Yes, casual shirts make excellent gifts for older men. Their practicality, lasting value, and timeless style mean they’re appreciated for a variety of occasions, from birthdays to holidays or simply as a thoughtful gesture.

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Casual Shirts For Older Men