Winter Dress Shirts

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160 Products
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Product Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-Blue/PinkAlternate Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Check Dress Shirt With Contrast Trim - Blue/pink Sale price$75.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

Blue/Pink
Save 47%
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-White/BlackAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White/black Sale price$69.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White/Black
Save 42%
Product Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-Blue/GreenAlternate Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Check Dress Shirt With Contrast Trim - Blue/green Sale price$75.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

Blue/Green
Save 47%
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-White/CobaltAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White/cobalt Sale price$69.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White/Cobalt
Save 42%
Product Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-Melon/BlueAlternate Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Check Dress Shirt With Contrast Trim - Melon/blue Sale price$75.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

Melon/Blue
Save 31%
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-White/CobaltAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White/cobalt Sale price$89.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White/Cobalt
Save 42%
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$75.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White
Save 42%
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-Melon/GreenAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - Melon/green Sale price$75.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

Melon/Green
Save 42%
Product Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-MelonAlternate Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Check Dress Shirt With Contrast Trim - Melon Sale price$75.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

Melon
3 for $199
Non-Iron Cotton Gingham Dress Shirt With Contrast Trim - Blue/redNon-Iron Cotton Gingham Dress Shirt With Contrast Trim - Blue/red
Non-Iron Cotton Gingham Dress Shirt With Contrast Trim - Blue/red Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Blue/Red
Save 42%
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-PurpleAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - Purple Sale price$75.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

Purple
3 for $199
Non-Iron Cotton Stripe Dress Shirt With Contrast Trim - RedNon-Iron Cotton Stripe Dress Shirt With Contrast Trim - Red
Non-Iron Cotton Stripe Dress Shirt With Contrast Trim - Red Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Red
Save 40%
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-WhiteComfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White Sale price$83.00 Regular price$139.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White
Save 31%
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-White/BlueComfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - White/blue
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - White/blue Sale price$89.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White/Blue
3 for $199
Product Image of Non-iron Cotton Windowpane Dress Shirt With Contrast Trim-PurpleNon-Iron Cotton Windowpane Dress Shirt With Contrast Trim - Purple
Non-Iron Cotton Windowpane Dress Shirt With Contrast Trim - Purple Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Purple
Save 47%
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-White/BlueAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White/blue Sale price$69.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White/Blue
Save 47%
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$69.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

Green
Save 31%
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-White/BlackAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White/black Sale price$89.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White/Black
Save 42%
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$75.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

Blue
3 for $199
Product Image of Non-iron Cotton Plaid Dress Shirt With Contrast Trim-BlueNon-Iron Cotton Plaid Dress Shirt With Contrast Trim - Blue
Non-Iron Cotton Plaid Dress Shirt With Contrast Trim - Blue Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Blue
Save 42%
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - WhiteComfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White Sale price$75.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White
3 for $199
Non-Iron Cotton Stripe Dress Shirt With Contrast Trim - CobaltAlternate Image of Non-iron Cotton Stripe Dress Shirt With Contrast Trim-1
Non-Iron Cotton Stripe Dress Shirt With Contrast Trim - Cobalt Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Cobalt
3 for $199
Non-Iron Cotton Stripe Dress Shirt With Contrast Trim - BlueAlternate Image of Non-iron Cotton Stripe Dress Shirt With Contrast Trim-1
Non-Iron Cotton Stripe Dress Shirt With Contrast Trim - Blue Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Blue
3 for $199
Product Image of Non-iron Cotton Gingham Dress Shirt With Contrast Trim-Blue/BrownAlternate Image of Non-iron Cotton Gingham Dress Shirt With Contrast Trim-1
Non-Iron Cotton Gingham Dress Shirt With Contrast Trim - Blue/brown Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Blue/Brown
3 for $199
Product Image of Non-iron Cotton Houndstooth Dress Shirt With Contrast Trim-Black/GreenNon-Iron Cotton Houndstooth Dress Shirt With Contrast Trim - Black/green
Non-Iron Cotton Houndstooth Dress Shirt With Contrast Trim - Black/green Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Black/Green
3 for $199
Product Image of Non-iron Cotton Check Dress Shirt With Contrast Trim-Purple/WhiteNon-Iron Cotton Check Dress Shirt With Contrast Trim - Purple/white
Non-Iron Cotton Check Dress Shirt With Contrast Trim - Purple/white Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Purple/White
3 for $199
Product Image of Non-iron Cotton Windowpane Dress Shirt With Contrast Trim-BlackAlternate Image of Non-iron Cotton Windowpane Dress Shirt With Contrast Trim-1
Non-Iron Cotton Windowpane Dress Shirt With Contrast Trim - Black Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Black
Save 31%
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-White/BlueAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White/blue Sale price$89.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White/Blue
Save 53%
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt-Light BlueAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt-1
Comfort Stretch Non-Iron Stripe Dress Shirt - Light Blue Sale price$79.00 Regular price$169.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

Light Blue
3 for $199
Product Image of Non-iron Cotton Stripe Dress Shirt With Contrast Trim-PurpleAlternate Image of Non-iron Cotton Stripe Dress Shirt With Contrast Trim-1
Non-Iron Cotton Stripe Dress Shirt With Contrast Trim - Purple Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Purple
3 for $199
Product Image of Non-iron Cotton Check Dress Shirt With Contrast Trim-Green/WhiteNon-Iron Cotton Check Dress Shirt With Contrast Trim - Green/white
Non-Iron Cotton Check Dress Shirt With Contrast Trim - Green/white Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Green/White
Save 42%
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$75.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White
Save 47%
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-White/PinkAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White/pink Sale price$69.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White/Pink
Save 53%
Product Image of Comfort Stretch Non-iron Check Dress Shirt-MultiComfort Stretch Non-Iron Check Dress Shirt - Multi
Comfort Stretch Non-Iron Check Dress Shirt - Multi Sale price$79.00 Regular price$169.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

Multi
3 for $199
Product Image of Non-iron Cotton Gingham Dress Shirt With Contrast Trim-Blue/BlackAlternate Image of Non-iron Cotton Gingham Dress Shirt With Contrast Trim-1
Non-Iron Cotton Gingham Dress Shirt With Contrast Trim - Blue/black Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Blue/Black
Save 47%
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-White/GreyAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White/grey Sale price$69.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White/Grey
3 for $199
Product Image of Non-iron Cotton Stripe Dress Shirt With Contrast Trim-GreenNon-Iron Cotton Stripe Dress Shirt With Contrast Trim - Green
Non-Iron Cotton Stripe Dress Shirt With Contrast Trim - Green Sale price$59.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Green
3 for $199
Product Image of Non-iron Cotton Check Dress Shirt With Contrast Trim-Blue/RedNon-Iron Cotton Check Dress Shirt With Contrast Trim - Blue/red
Non-Iron Cotton Check Dress Shirt With Contrast Trim - Blue/red Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Blue/Red
3 for $199
Product Image of Non-iron Cotton Check Dress Shirt With Contrast Trim-Brown/WhiteNon-Iron Cotton Check Dress Shirt With Contrast Trim - Brown/white
Non-Iron Cotton Check Dress Shirt With Contrast Trim - Brown/white Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Brown/White
3 for $199
Product Image of Non-iron Cotton Stripe Dress Shirt With Contrast Trim-GreenAlternate Image of Non-iron Cotton Stripe Dress Shirt With Contrast Trim-1
Non-Iron Cotton Stripe Dress Shirt With Contrast Trim - Green Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Green
3 for $199
Product Image of Non-iron Cotton Plaid Dress Shirt With Contrast Trim-Blue/PurpleNon-Iron Cotton Plaid Dress Shirt With Contrast Trim - Blue/purple
Non-Iron Cotton Plaid Dress Shirt With Contrast Trim - Blue/purple Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Blue/Purple
Save 42%
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$75.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

White
Save 42%
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - Blue/yellowAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - Blue/yellow Sale price$75.00 Regular price$129.00

Labor Day Sale: Extra $25 off $125+ | Ends 9/1

Blue/Yellow
3 for $199
Product Image of Non-iron Cotton Solid Dress Shirt With Contrast Trim-GreenAlternate Image of Non-iron Cotton Solid Dress Shirt With Contrast Trim-1
Non-Iron Cotton Solid Dress Shirt With Contrast Trim - Green Sale price$69.00 Regular price$119.00

3 for $199 Bundle *Excludes other offers

Green

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.