Dressy Shirts

Elevate your wardrobe with our collection of dressy shirts, perfect for any occasion where a touch of refinement is needed. These versatile shirts are designed to seamlessly transition from a day at the office to an evening out, offering both comfort and style. Crafted with attention to detail and quality materials, our dressy shirts provide lasting value and timeless appeal. Whether paired with tailored trousers or your favorite jeans, these shirts add a polished touch to any ensemble, ensuring you always look your best. Explore a variety of colors and styles that suit every taste and occasion, making it easy to find the perfect shirt for your needs.

Sort by:

Filter & Sort

298 Items

Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check

A wrinkle-free blue check shirt made from 100% cotton poplin with moisture-wicking TrueCool® fabric.

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

A wrinkle-free pinpoint oxford shirt in blue cotton with a traditional fit and durable stitching.

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

A wrinkle-free, bright blue tattersall oxford shirt with a traditional fit and ultrasmooth 100% cotton fabric.

Pros: High quality Perfect fit Wrinkle-free Durable Comfortable
Women's Wrinkle-Free Pinpoint Oxford Shirt, Long-Sleeve Relaxed Fit

A wrinkle-free, 100% cotton pinpoint oxford shirt with a relaxed fit and pearlized buttons.

Pros: High quality Wrinkle-free Crisp and professional look Versatile Comfortable fit
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit

A white cotton blend oxford shirt with moisture-wicking stretch fabric, perfect for untucked wear.

Pros: Good appearance Material quality Well-made Comfortable
Women's Wrinkle-Free Pinpoint Oxford Shirt, Relaxed Fit Long-Sleeve Print

A relaxed-fit, multi-color print shirt made from wrinkle-free pinpoint cotton for all-day smoothness.

Pros: Comfortable and lightweight Versatile and well-fitting Attractive color and pattern High quality and durable Wrinkle-free fabric
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check

A deep green, wrinkle-free cotton shirt with moisture-wicking TrueCool® fabric and a relaxed traditional fit.

Pros: Generous fit High quality Wrinkle-free Easy to wear Comfortable fabric
Women's Wrinkle-Free Pinpoint Oxford Shirt, Long-Sleeve Relaxed Fit Plaid
Price was from: $79.95 now: $54.99

A versatile multi-color plaid shirt in wrinkle-free cotton with a relaxed fit and pearlized buttons.

Pros: High-quality material Wrinkle-free Easy to care for Versatile and classic look Comfortable fit
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
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
Price was from: $89 now: $49.99

A slim-fit plaid shirt in golden cider, made from 100% cotton flannel for vintage softness.

Pros: Beautiful design High quality Warmth Soft fabric Comfortable fit
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid

A bayside blue plaid oxford shirt with moisture-wicking cotton blend and stretch for comfort.

Pros: Lovely color High quality material Stylish Comfortable Good fit
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit

A slim-fit chamois flannel shirt in barley, made from 100% cotton and brushed for softness.

Pros: Perfect fit Great quality Softness Warmth Durability
Men's Organic Cotton Seersucker Shirt, Short-Sleeve, Slightly Fitted, Plaid
Price was from: $49.95 now: $39.99

A breathable yellow plaid shirt in 100% organic cotton seersucker with a slightly fitted design.

Pros: High quality Breathable fabric Stylish design Versatile look Comfortable fit
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $44.99

A goldenrod plaid oxford shirt with moisture-wicking cotton blend and stretch for comfort and ease of movement.

Pros: High quality fabric Perfect fit Comfort Wrinkle-free after washing Untucked design
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit

A light cobalt cotton blend shirt with moisture-wicking and stretch, designed for untucked wear.

Pros: Quality fabric Versatile Good fit Dressy yet comfortable Casual style
Women's Signature Linen-Blend Button-Front Shirt, Sleeveless
Price was from: $79 now: $54.99

A sleeveless blue shirt with a linen-rayon blend, offering a cool, comfortable drape and tulip hem.
Men's Comfort Stretch Performance® Shirt, Short-Sleeve, Slightly Fitted Untucked Fit
Price was from: $59.95 now: $44.99

A green short-sleeve shirt with moisture-wicking stretch fabric, perfect for untucked wear.
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $74.95 now: $49.99

A green chambray shirt offering moisture-wicking comfort with a slightly fitted untucked fit and hidden features.
Women's Premium Washable Linen Shirt, Splitneck Stripe
Price was from: $64.95 now: $54.99

A cool and breathable 100% linen shirt with bracelet-length sleeves and a curved high-low hem.
Men's Stonecoast Hemp Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $49.99

A deep blue, slightly fitted shirt made from a breathable hemp/cotton blend with a touch of spandex.
Men's Stonecoast Hemp Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Stripe

A slightly fitted, untucked cotton blend shirt in silver birch with a stylish stripe pattern.
Men's Signature Stretch Poplin Shirt, Short-Sleeve, Slim Fit
Price was from: $69.95 now: $44.99

A slim-fit brown short-sleeve shirt in soft cotton blend, perfect for casual, untucked wear.
Women's Premium Washable Linen Shirt, Splitneck
Price was from: $59.95 now: $44.99

A cool, breathable pink linen shirt with a splitneck and bracelet-length sleeves, machine washable.
Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
Price was from: $79 now: $54.99

An indigo ink slim-fit shirt made from a soft, stretchy cotton blend, perfect for casual wear.

Dressy Shirts

When it comes to dressing for occasions that call for a little extra polish, the right shirt can make all the difference. Dressy shirts are a wardrobe essential for anyone who appreciates versatile style and lasting comfort, whether you're heading to the office, gathering with friends, or celebrating family milestones. As the days grow shorter and September brings a crispness to the air, it's a great time to refresh your closet with shirts that feel just as comfortable layered under a sweater as they do on their own. The best dressy shirts are thoughtfully crafted with details that stand out—think smooth, durable fabrics that hold their shape, button-down collars that stay neat, and subtle patterns or classic solids that never go out of style. These shirts are designed to move with you throughout your day, offering a reliable option for everything from important meetings to dinner out. They’re also easy to care for, so you can spend less time worrying about wrinkles and more time focusing on what matters most.

Dressy shirts also make a thoughtful gift for loved ones who appreciate quality and versatility. They’re a welcome addition to any wardrobe, suitable for teachers, colleagues, friends, or family members who value clothing that transitions seamlessly from work to weekend. Many people find themselves reaching for their favorite dressy shirt for special occasions—holiday gatherings, milestone birthdays, or even casual weddings—knowing it will help them look and feel their best. A well-made shirt can be paired with everything from tailored pants to comfortable jeans, making it a go-to piece season after season. When selecting the right shirt, it’s worth considering details like breathability, softness, and ease of layering. Classic features such as button cuffs, chest pockets, and flattering silhouettes ensure these shirts remain timeless, while subtle updates in color and pattern keep your look fresh year after year. For women looking to update their wardrobe with practical yet stylish options, our collection of Women's Dress Shirts offers a range of choices designed with comfort, durability, and timeless appeal in mind.

As autumn settles in, dressy shirts become especially handy for navigating the changing temperatures and shifting social calendars. Imagine a crisp September morning, slipping into a shirt that feels soft against your skin and looks just right under a favorite cardigan or blazer. Later, as the day warms up, you can roll up the sleeves and stay comfortable at a backyard barbecue or a weekend outing. These shirts are designed to be easy to wear and even easier to love, offering the kind of lasting value that comes from quality materials and expert craftsmanship. Whether you’re shopping for yourself or looking for a gift that’s sure to be appreciated, dressy shirts are a reliable choice that blends classic style with everyday practicality. With so many options to choose from, you’re sure to find the perfect fit for any occasion, making it simple to step out with confidence and enjoy everything the season has to offer.

FAQs

Dressy shirts are often made from high-quality materials such as cotton, linen, and blends that include polyester or spandex for added comfort and durability. These fabrics are chosen for their smooth texture, breathability, and ability to drape well, ensuring a polished look that feels great all day.

Dressy shirts are incredibly versatile and can be styled in a variety of ways. For a casual look, pair your shirt with jeans or chinos and roll up the sleeves. For more formal settings, tuck your shirt into tailored pants or a skirt, and add a blazer or cardigan. Accessories like belts and subtle jewelry can further elevate your outfit.

Absolutely. Dressy shirts are ideal for layering during fall and winter. Their streamlined silhouettes make them easy to wear under sweaters, vests, or blazers, providing extra warmth without bulk. Look for shirts with comfortable, breathable fabrics to ensure you stay cozy and stylish as the temperatures drop.

Key features to consider include durable stitching, reinforced seams, quality buttons, and collars that retain their shape. Details such as button cuffs, chest pockets, and timeless patterns or colors also add to a shirt’s overall appeal and versatility.

Dressy shirts make thoughtful gifts for friends, family, or colleagues, especially for those who appreciate classic style and lasting value. Their versatility means they can be worn for a variety of occasions, making them a practical and appreciated addition to any wardrobe.

It's time to upgrade your browser

Dressy Shirts

Dressy Shirts

Popular Items

FAQs

Recommended

It's time to upgrade your browser

Dressy Shirts

Dressy Shirts

Popular Items

Related Pages

FAQs

Top Collections