Winter Dress Shirts

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185 Products
Product Image of Comfort Stretch Non-iron Novelty Dress Shirt With Contrast Trim-Red/GreenAlternate Image of Comfort Stretch Non-iron Novelty Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Novelty Dress Shirt With Contrast Trim - Red/green Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Red/Green
Product Image of Comfort Stretch Non-iron Windowpane Dress Shirt With Contrast Trim-GreenAlternate Image of Comfort Stretch Non-iron Windowpane Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Windowpane Dress Shirt With Contrast Trim - Green Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Green
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-White MultiAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White Multi Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

White Multi
Product Image of Comfort Stretch Non-iron Dot Dress Shirt-MultiAlternate Image of Comfort Stretch Non-iron Dot Dress Shirt-1
Comfort Stretch Non-Iron Dot Dress Shirt - Multi Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Multi
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-Red/GreenAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - Red/green Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Red/Green
Product Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-Green/BlueAlternate Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Plaid Dress Shirt With Contrast Trim - Green/blue Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Green/Blue
Product Image of Comfort Stretch Non-iron Plaid Dress Shirt-RedAlternate Image of Comfort Stretch Non-iron Plaid Dress Shirt-1
Comfort Stretch Non-Iron Plaid Dress Shirt - Red Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Red
Product Image of Comfort Stretch Non-iron Novelty Dress Shirt With Contrast Trim-BlackAlternate Image of Comfort Stretch Non-iron Novelty Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Novelty Dress Shirt With Contrast Trim - Black Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Black
Product Image of Comfort Stretch Non-iron Novelty Dress Shirt With Contrast Trim-RedAlternate Image of Comfort Stretch Non-iron Novelty Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Novelty Dress Shirt With Contrast Trim - Red Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Red
Product Image of Comfort Stretch Non-iron Novelty Dress Shirt With Contrast Trim-Red/GreenAlternate Image of Comfort Stretch Non-iron Novelty Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Novelty Dress Shirt With Contrast Trim - Red/green Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Red/Green
Product Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-White MultiAlternate Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Plaid Dress Shirt With Contrast Trim - White Multi Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

White Multi
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-BlackAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - Black Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Black
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-WhiteAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

White
Product Image of Comfort Stretch Non-iron Novelty Dress Shirt With Contrast Trim-GreenAlternate Image of Comfort Stretch Non-iron Novelty Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Novelty Dress Shirt With Contrast Trim - Green Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Green
3 for $199
Product Image of Non-iron Cotton Solid Dress Shirt With Contrast Trim-CobaltAlternate Image of Non-iron Cotton Solid Dress Shirt With Contrast Trim-1
Non-Iron Cotton Solid Dress Shirt With Contrast Trim - Cobalt Sale price$119.00

3 for $199 Essential Shirts | Special Bundle Offer

Cobalt
Product Image of Comfort Stretch Non-iron Dot Dress Shirt With Contrast Trim-BurgundyAlternate Image of Comfort Stretch Non-iron Dot Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Dot Dress Shirt With Contrast Trim - Burgundy Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Burgundy
Product Image of Comfort Stretch Non-iron Plaid Dress Shirt-BlackAlternate Image of Comfort Stretch Non-iron Plaid Dress Shirt-1
Comfort Stretch Non-Iron Plaid Dress Shirt - Black Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Black
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-BlueAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - Blue Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Blue
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-Blue/RedAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - Blue/red Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Blue/Red
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-Navy/RedAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - Navy/red Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Navy/Red
Product Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-Green/RustAlternate Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Check Dress Shirt With Contrast Trim - Green/rust Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Green/Rust
Product Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-Red/GreenAlternate Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Plaid Dress Shirt With Contrast Trim - Red/green Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Red/Green
Product Image of Comfort Stretch Non-iron Botanical Dress Shirt With Contrast Trim-CharcoalAlternate Image of Comfort Stretch Non-iron Botanical Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Botanical Dress Shirt With Contrast Trim - Charcoal Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Charcoal
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-MultiAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - Multi Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Multi
Product Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-Navy/RedAlternate Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Plaid Dress Shirt With Contrast Trim - Navy/red Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Navy/Red
Product Image of Comfort Stretch Non-iron Paisley Dress Shirt With Contrast Trim-BurgundyAlternate Image of Comfort Stretch Non-iron Paisley Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Paisley Dress Shirt With Contrast Trim - Burgundy Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Burgundy
Product Image of Comfort Stretch Non-iron Check Dress Shirt-BurgundyAlternate Image of Comfort Stretch Non-iron Check Dress Shirt-1
Comfort Stretch Non-Iron Check Dress Shirt - Burgundy Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Burgundy
Product Image of Comfort Stretch Non-iron Check Dress Shirt-NavyAlternate Image of Comfort Stretch Non-iron Check Dress Shirt-1
Comfort Stretch Non-Iron Check Dress Shirt - Navy Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Navy
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-BlackAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - Black Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Black
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-GreenAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - Green Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Green
Product Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-GreenAlternate Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Plaid Dress Shirt With Contrast Trim - Green Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Green
Product Image of Comfort Stretch Non-iron Plaid Dress Shirt-Navy/GreenAlternate Image of Comfort Stretch Non-iron Plaid Dress Shirt-1
Comfort Stretch Non-Iron Plaid Dress Shirt - Navy/green Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Navy/Green
Product Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-1Alternate Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Plaid Dress Shirt With Contrast Trim - Green/red Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Green/red
Product Image of Comfort Stretch Non-iron Novelty Dress Shirt With Contrast Trim-RedAlternate Image of Comfort Stretch Non-iron Novelty Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Novelty Dress Shirt With Contrast Trim - Red Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Red
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-Black MultiAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - Black Multi Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Black Multi
Product Image of Comfort Stretch Non-iron Check Dress Shirt-BlackAlternate Image of Comfort Stretch Non-iron Check Dress Shirt-1
Comfort Stretch Non-Iron Check Dress Shirt - Black Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Black
Product Image of Comfort Stretch Non-iron Geometric Dress Shirt With Contrast Trim-Black/RedAlternate Image of Comfort Stretch Non-iron Geometric Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Geometric Dress Shirt With Contrast Trim - Black/red Sale price$149.00

Buy One, Get One 50% Off | Ends 10/23

Black/Red
Product Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-Black/RedAlternate Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Check Dress Shirt With Contrast Trim - Black/red Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Black/Red
Product Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-Navy MultiAlternate Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Check Dress Shirt With Contrast Trim - Navy Multi Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Navy Multi
Product Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-MultiAlternate Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Plaid Dress Shirt With Contrast Trim - Multi Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Multi
Product Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-Navy/GoldAlternate Image of Comfort Stretch Non-iron Plaid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Plaid Dress Shirt With Contrast Trim - Navy/gold Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Navy/Gold
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-Navy/GoldAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - Navy/gold Sale price$129.00

Buy One, Get One 50% Off | Ends 10/23

Navy/Gold

Stay sharp and warm with our Winter Dress Shirt Collection—perfect for any occasion. Men's winter dress shirts are a staple in any man's wardrobe during the colder months. These dress shirts are designed to keep you warm while maintaining a sharp and sophisticated appearance. Made from thicker fabrics such as wool or cotton blends, they offer additional insulation against the cold. Some of our winter dress shirts feature patterns or prints that are reminiscent of the season, such as plaid or checkered designs. We even have winter shirts designed specifically for the Holidays. No matter the season, Paul Fredrick has you covered. Plus, our men's winter dress shirts are a versatile garment that can be dressed up or down, making them perfect for any formal occasion during the winter season. Pair a winter dress shirt with dark jeans or chinos for a more casual look. Add a pair of sneakers or loafers to complete the outfit. Pair the winter dress shirt with a black suit and a solid white or black tie for a formal and elegant look. At Paul Fredrick we pride ourselves by paying attention to the detail in our dress shirts, including collar styles and cuff designs, resulting in a high-quality and stylish shirt. Shop a fashionable winter dress shirts at Paul Fredrick—perfect fit guaranteed.