Winter Dress Shirts

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134 Products
2 for $59 Each
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-Blue/PinkAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - Blue/pink Sale price$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

Blue/Pink
2 for $59 Each
Product Image of 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$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

Blue/Yellow
2 for $59 Each
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$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

White/Black
2 for $59 Each
Product Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-YellowAlternate Image of Comfort Stretch Non-iron Check Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Check Dress Shirt With Contrast Trim - Yellow Sale price$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

Yellow
2 for $59 Each
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-PinkAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - Pink Sale price$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

Pink
2 for $59 Each
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$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

White/Cobalt
2 for $59 Each
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$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

White/Pink
2 for $59 Each
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$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

Green
2 for $59 Each
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$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

White/Blue
2 for $59 Each
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$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

White
2 for $59 Each
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1Alternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White/gold Sale price$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

White/gold
2 for $59 Each
Product Image of Comfort Stretch Non-iron Herringbone Dress Shirt-YellowAlternate Image of Comfort Stretch Non-iron Herringbone Dress Shirt-1
Comfort Stretch Non-Iron Herringbone Dress Shirt - Yellow Sale price$79.00 Regular price$169.00

$59 Each When You Buy 2 *Excludes other offers

Yellow
2 for $59 Each
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

$59 Each When You Buy 2 *Excludes other offers

Light Blue
2 for $59 Each
Product Image of Comfort Stretch Non-iron Check Dress Shirt-MultiAlternate Image of Comfort Stretch Non-iron Check Dress Shirt-1
Comfort Stretch Non-Iron Check Dress Shirt - Multi Sale price$79.00 Regular price$169.00

$59 Each When You Buy 2 *Excludes other offers

Multi
2 for $59 Each
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-White/PurpleAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White/purple Sale price$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

White/Purple
2 for $59 Each
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$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

White/Grey
2 for $59 Each
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-White/PurpleAlternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White/purple Sale price$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

White/Purple
2 for $59 Each
Product Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1Alternate Image of Comfort Stretch Non-iron Solid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Solid Dress Shirt With Contrast Trim - White/gold Sale price$79.00 Regular price$129.00

$59 Each When You Buy 2 *Excludes other offers

White/gold
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

BOGO 50% Off | Ends 6/30

White
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$129.00

BOGO 50% Off | Ends 6/30

Melon
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$129.00

BOGO 50% Off | Ends 6/30

Blue/Pink
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$129.00

BOGO 50% Off | Ends 6/30

Blue
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$129.00

BOGO 50% Off | Ends 6/30

Melon/Blue
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$129.00

BOGO 50% Off | Ends 6/30

Purple
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

BOGO 50% Off | Ends 6/30

White
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$129.00

BOGO 50% Off | Ends 6/30

Blue/Green
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$129.00

BOGO 50% Off | Ends 6/30

Melon/Green
3 for $199
Product Image of Non-iron Cotton Pinpoint Solid Point Collar Dress Shirt-WhiteAlternate Image of Non-iron Cotton Pinpoint Solid Point Collar Dress Shirt-1
Non-Iron Cotton Pinpoint Solid Point Collar Dress Shirt - White Sale price$119.00

3 for $199 Bundle *Excludes other offers

Blue
White
Pink
Black
3 for $199
Product Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-WhiteAlternate Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-1
Non-Iron Cotton Pinpoint Solid Button Down Collar Dress Shirt - White Sale price$119.00

3 for $199 Bundle *Excludes other offers

White
French Blue
Blue
Blue Stripe
3 for $199
Product Image of Non-iron Cotton Pinpoint Solid Point Collar French Cuff Dress Shirt-WhiteAlternate Image of Non-iron Cotton Pinpoint Solid Point Collar French Cuff Dress Shirt-1
Non-Iron Cotton Pinpoint Solid Point Collar French Cuff Dress Shirt - White Sale price$119.00

3 for $199 Bundle *Excludes other offers

White
Grey
Black
Blue
3 for $199
Product Image of Non-iron Cotton Pinpoint Solid Point Collar Dress Shirt-BlueAlternate Image of Non-iron Cotton Pinpoint Solid Point Collar Dress Shirt-1
Non-Iron Cotton Pinpoint Solid Point Collar Dress Shirt - Blue Sale price$119.00

3 for $199 Bundle *Excludes other offers

Blue
White
Pink
Black
3 for $199
Product Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-BlueAlternate Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-1
Non-Iron Cotton Pinpoint Solid Button Down Collar Dress Shirt - Blue Sale price$119.00

3 for $199 Bundle *Excludes other offers

White
French Blue
Blue
Blue Stripe
3 for $199
Product Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-French BlueAlternate Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-1
Non-Iron Cotton Pinpoint Solid Button Down Collar Dress Shirt - French Blue Sale price$119.00

3 for $199 Bundle *Excludes other offers

White
French Blue
Blue
Blue Stripe
3 for $199
Product Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-Blue StripeAlternate Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-1
Non-Iron Cotton Pinpoint Solid Button Down Collar Dress Shirt - Blue Stripe Sale price$119.00

3 for $199 Bundle *Excludes other offers

White
French Blue
Blue
Blue Stripe
Save 31%
Product Image of Comfort Stretch Non-iron Gingham Dress Shirt With Contrast Trim-Blue/PurpleAlternate Image of Comfort Stretch Non-iron Gingham Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Gingham Dress Shirt With Contrast Trim - Blue/purple Sale price$89.00 Regular price$129.00

BOGO 50% Off | Ends 6/30

Blue/Purple
Save 31%
Product Image of Comfort Stretch Non-iron Glen Plaid Dress Shirt With Contrast Trim-BlueAlternate Image of Comfort Stretch Non-iron Glen Plaid Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Glen Plaid Dress Shirt With Contrast Trim - Blue Sale price$89.00 Regular price$129.00

BOGO 50% Off | Ends 6/30

Blue
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$129.00

BOGO 50% Off | Ends 6/30

White/Cobalt
3 for $199
Product Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-YellowAlternate Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-1
Non-Iron Cotton Pinpoint Solid Button Down Collar Dress Shirt - Yellow Sale price$119.00

3 for $199 Bundle *Excludes other offers

White
French Blue
Blue
Blue Stripe
3 for $199
Product Image of Non-iron Cotton Pinpoint Solid Spread Collar Dress Shirt-WhiteAlternate Image of Non-iron Cotton Pinpoint Solid Spread Collar Dress Shirt-1
Non-Iron Cotton Pinpoint Solid Spread Collar Dress Shirt - White Sale price$119.00

3 for $199 Bundle *Excludes other offers

White
Blue
Save 8%
Product Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-YellowAlternate Image of Comfort Stretch Non-iron Stripe Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Stripe Dress Shirt With Contrast Trim - Yellow Sale price$119.00 Regular price$129.00

BOGO 50% Off | Ends 6/30

Yellow
3 for $199
Product Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-PinkAlternate Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-1
Non-Iron Cotton Pinpoint Solid Button Down Collar Dress Shirt - Pink Sale price$119.00

3 for $199 Bundle *Excludes other offers

White
French Blue
Blue
Blue Stripe
3 for $199
Product Image of Non-iron Cotton Pinpoint Solid Point Collar Dress Shirt-EcruAlternate Image of Non-iron Cotton Pinpoint Solid Point Collar Dress Shirt-1
Non-Iron Cotton Pinpoint Solid Point Collar Dress Shirt - Ecru Sale price$119.00

3 for $199 Bundle *Excludes other offers

Blue
White
Pink
Black
3 for $199
Product Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-LavenderAlternate Image of Non-iron Cotton Pinpoint Solid Button Down Collar Dress Shirt-1
Non-Iron Cotton Pinpoint Solid Button Down Collar Dress Shirt - Lavender Sale price$119.00

3 for $199 Bundle *Excludes other offers

White
French Blue
Blue
Blue Stripe
Save 23%
Product Image of Comfort Stretch Non-iron Tattersall Dress Shirt With Contrast Trim-Blue/PinkAlternate Image of Comfort Stretch Non-iron Tattersall Dress Shirt With Contrast Trim-1
Comfort Stretch Non-Iron Tattersall Dress Shirt With Contrast Trim - Blue/pink Sale price$99.00 Regular price$129.00

BOGO 50% Off | Ends 6/30

Blue/Pink

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.