Shop Tailored Shirts Chicago

Sponsored
$19.99
Men's Jos. A. Bank Tailored Fit Button-Down Collar Bengal Stripe Dress Shirt Clearance At Jos. A. Bank, Blue, Size 17 X 34/35
Jos. A. Bank Clothiers, Inc.
$19.99
Men's Jos. A. Bank Tailored Fit Button-Down Collar Bengal Stripe Dress Shirt Clearance At Jos. A. Bank, Blue, Size 17 X 34/35
Jos. A. Bank Clothiers, Inc.
$25.98
Lion Nardo Mens Dress Shirts Long Sleeve Dress Shirts For Men Wrinkle Free Button Down Shirts Big Linen Shirts For Men
Amazon.com
37
$25.98
Lion Nardo Mens Dress Shirts Long Sleeve Dress Shirts For Men Wrinkle Free Button Down Shirts Big Linen Shirts For Men
Amazon.com
$41.97
$69.95
Men's Tailored Fit No Iron Solid Supima Cotton Oxford Dress Shirt - Lands' End - Blue - 16 32
Lands' End
39% off
$41.97
$69.95
Men's Tailored Fit No Iron Solid Supima Cotton Oxford Dress Shirt - Lands' End - Blue - 16 32
Lands' End
$42.50
Tommy Hilfiger Men's Dress Shirt Regular Fit Essentials
Amazon.com
Free shipping
$42.50
Tommy Hilfiger Men's Dress Shirt Regular Fit Essentials
Amazon.com
$35.95
Men's Long Sleeve Tailored Straight Collar Broadcloth Dress Shirt - Lands' End - Blue - 15H35
Lands' End
$35.95
Men's Long Sleeve Tailored Straight Collar Broadcloth Dress Shirt - Lands' End - Blue - 15H35
Lands' End
$44.97
$74.95
Men's Tailored Fit No Iron Solid Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Blue - 15 34
Lands' End
39% off
$44.97
$74.95
Men's Tailored Fit No Iron Solid Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Blue - 15 34
Lands' End
$30.27
Van Heusen Men's Pinpoint Regular Fit Solid Button Down Collar Dress Shirt
Amazon.com
2K+
$30.27
Van Heusen Men's Pinpoint Regular Fit Solid Button Down Collar Dress Shirt
Amazon.com
$19.99
Men's Traveler Collection Tailored Fit Spread Collar Check Dress Shirt Clearance At Jos. A. Bank, Blue/Cream/White, Size 17 X 34/35
Jos. A. Bank Clothiers, Inc.
$19.99
Men's Traveler Collection Tailored Fit Spread Collar Check Dress Shirt Clearance At Jos. A. Bank, Blue/Cream/White, Size 17 X 34/35
Jos. A. Bank Clothiers, Inc.
$44.97
$74.95
Men's Tailored Fit No Iron Solid Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Blue - 17 33
Lands' End
39% off
$44.97
$74.95
Men's Tailored Fit No Iron Solid Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Blue - 17 33
Lands' End
$26.07
Van Heusen Men's Dress Shirts Short Sleeve Oxford Solid
Amazon.com
3K+
$26.07
Van Heusen Men's Dress Shirts Short Sleeve Oxford Solid
Amazon.com
$41.97
$69.95
Men's Tall Tailored Fit No Iron Solid Supima Cotton Oxford Dress Shirt - Lands' End - Blue - 16H37
Lands' End
39% off
$41.97
$69.95
Men's Tall Tailored Fit No Iron Solid Supima Cotton Oxford Dress Shirt - Lands' End - Blue - 16H37
Lands' End
$38.31
STACY ADAMS Men's Regular Fit Big & Tall Solid Dress Shirt
Amazon.com
1K+
Free shipping
$38.31
STACY ADAMS Men's Regular Fit Big & Tall Solid Dress Shirt
Amazon.com
$47.99
Neil Allyn Tuxedo Shirt 100% Cotton With Laydown Collar And French Cuffs
Amazon.com
693
Free shipping
$47.99
Neil Allyn Tuxedo Shirt 100% Cotton With Laydown Collar And French Cuffs
Amazon.com
$25.19
Alimens & Gentle French Cuff Regular Fit Dress Shirts (Cufflink Included) White New 17.5" Neck 36" Sleeve
Amazon.com
11K+
$25.19
Alimens & Gentle French Cuff Regular Fit Dress Shirts (Cufflink Included) White New 17.5" Neck 36" Sleeve
Amazon.com
$41.97
$69.95
Men's Tall Tailored Fit No Iron Twill Long Sleeve Shirt - Lands' End - White - XL
Lands' End
39% off
$41.97
$69.95
Men's Tall Tailored Fit No Iron Twill Long Sleeve Shirt - Lands' End - White - XL
Lands' End
$19.99
Van Heusen Men's Dress Shirt Fitted Poplin Solid White 18.5" Neck 36"-37" Sleeve
Amazon.com
21K+
$19.99
Van Heusen Men's Dress Shirt Fitted Poplin Solid White 18.5" Neck 36"-37" Sleeve
Amazon.com
$19.99
Men's Jos. A. Bank Tailored Fit Spread Collar Mini Gingham Dress Shirt Clearance At Jos. A. Bank, Blue/Navy, Size 14 1 /2 X 32/33
Jos. A. Bank Clothiers, Inc.
$19.99
Men's Jos. A. Bank Tailored Fit Spread Collar Mini Gingham Dress Shirt Clearance At Jos. A. Bank, Blue/Navy, Size 14 1 /2 X 32/33
Jos. A. Bank Clothiers, Inc.
$44.97
$74.95
Men's Tailored Fit No Iron Pattern Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Orange - 16 33
Lands' End
39% off
$44.97
$74.95
Men's Tailored Fit No Iron Pattern Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Orange - 16 33
Lands' End
$44.97
$74.95
Men's Tailored Fit No Iron Pattern Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Blue - 16 33
Lands' End
39% off
$44.97
$74.95
Men's Tailored Fit No Iron Pattern Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Blue - 16 33
Lands' End
$44.97
$74.95
Men's Tailored Fit No Iron Pattern Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Gray - 16 35
Lands' End
39% off
$44.97
$74.95
Men's Tailored Fit No Iron Pattern Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Gray - 16 35
Lands' End
$41.97
$69.95
Men's Tailored Fit No Iron Solid Supima Cotton Oxford Dress Shirt - Lands' End - White - 15 32
Lands' End
39% off
$41.97
$69.95
Men's Tailored Fit No Iron Solid Supima Cotton Oxford Dress Shirt - Lands' End - White - 15 32
Lands' End
$14.89
Beninos Mens Slim Fit Solid Point Collar Button Down Dress Shirt
Amazon.com
3K+
$14.89
Beninos Mens Slim Fit Solid Point Collar Button Down Dress Shirt
Amazon.com
$74.95
Men's Tailored Fit No Iron Solid Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - White - 17 34
Lands' End
$74.95
Men's Tailored Fit No Iron Solid Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - White - 17 34
Lands' End
$35.97
$59.95
Men's Tailored Fit Long Sleeve Sail Rigger Oxford Shirt - Lands' End - Blue - L
Lands' End
39% off
$35.97
$59.95
Men's Tailored Fit Long Sleeve Sail Rigger Oxford Shirt - Lands' End - Blue - L
Lands' End
$27.39
Van Heusen Mens Dress Shirt Oxford Solid Regular Fit White 17.5" Neck 34"-35" Sleeve
Amazon.com
9K+
$27.39
Van Heusen Mens Dress Shirt Oxford Solid Regular Fit White 17.5" Neck 34"-35" Sleeve
Amazon.com
$44.97
$74.95
Men's Tailored Fit No Iron Pattern Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Tan - 16 32
Lands' End
39% off
$44.97
$74.95
Men's Tailored Fit No Iron Pattern Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Tan - 16 32
Lands' End
$44.97
$74.95
Men's Tailored Fit No Iron Pattern Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Blue - 16 32
Lands' End
39% off
$44.97
$74.95
Men's Tailored Fit No Iron Pattern Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Blue - 16 32
Lands' End
$35.97
$59.95
Men's Tailored Fit Long Sleeve Sail Rigger Oxford Shirt - Lands' End - White - L
Lands' End
39% off
$35.97
$59.95
Men's Tailored Fit Long Sleeve Sail Rigger Oxford Shirt - Lands' End - White - L
Lands' End
$19.99
Van Heusen Men's Dress Shirt Regular Fit Poplin Solid White 18.5" Neck 32"-33" Sleeve
Amazon.com
36K+
$19.99
Van Heusen Men's Dress Shirt Regular Fit Poplin Solid White 18.5" Neck 32"-33" Sleeve
Amazon.com
$35.95
Men's Long Sleeve Tailored Straight Collar Broadcloth Dress Shirt - Lands' End - Black - 14H33
Lands' End
$35.95
Men's Long Sleeve Tailored Straight Collar Broadcloth Dress Shirt - Lands' End - Black - 14H33
Lands' End
$35.00
$70.00
Women's Tailored Easy-Care Shirt Black Petite Size 0
Banana Republic Factory
50% off
$35.00
$70.00
Women's Tailored Easy-Care Shirt Black Petite Size 0
Banana Republic Factory
$133.00
Beige 100% Cotton Tailored Shirt With Contrast Collar
Hockerty.com
$133.00
Beige 100% Cotton Tailored Shirt With Contrast Collar
Hockerty.com
$358.37
$756.86
Dolce & Gabbana Classic Tailored-Cut Shirt For - White - Casual Shirts Size 40cm
Cettire
52% off
$358.37
$756.86
Dolce & Gabbana Classic Tailored-Cut Shirt For - White - Casual Shirts Size 40cm
Cettire
$14.99
Long Sleeve Dress Shirts For Men - Regular-Fit Casual Button-Down Shirt With Pockets Black Medium
Amazon.com
976
$14.99
Long Sleeve Dress Shirts For Men - Regular-Fit Casual Button-Down Shirt With Pockets Black Medium
Amazon.com
$91.00
Black 100% Cotton Tailored Shirt With Contrast Collar At Hockerty
Hockerty.com
$91.00
Black 100% Cotton Tailored Shirt With Contrast Collar At Hockerty
Hockerty.com
$35.00
$70.00
Women's Tailored Easy-Care Shirt White Regular Size 16
Banana Republic Factory
50% off
$35.00
$70.00
Women's Tailored Easy-Care Shirt White Regular Size 16
Banana Republic Factory
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    Shop Tailored Shirts Chicago

    Sponsored
    $19.99
    Men's Jos. A. Bank Tailored Fit Button-Down Collar Bengal Stripe Dress Shirt Clearance At Jos. A. Bank, Blue, Size 17 X 34/35
    Jos. A. Bank Clothiers, Inc.
    $19.99
    Men's Jos. A. Bank Tailored Fit Button-Down Collar Bengal Stripe Dress Shirt Clearance At Jos. A. Bank, Blue, Size 17 X 34/35
    Jos. A. Bank Clothiers, Inc.
    $25.98
    Lion Nardo Mens Dress Shirts Long Sleeve Dress Shirts For Men Wrinkle Free Button Down Shirts Big Linen Shirts For Men
    Amazon.com
    37
    $25.98
    Lion Nardo Mens Dress Shirts Long Sleeve Dress Shirts For Men Wrinkle Free Button Down Shirts Big Linen Shirts For Men
    Amazon.com
    $41.97
    $69.95
    Men's Tailored Fit No Iron Solid Supima Cotton Oxford Dress Shirt - Lands' End - Blue - 16 32
    Lands' End
    39% off
    $41.97
    $69.95
    Men's Tailored Fit No Iron Solid Supima Cotton Oxford Dress Shirt - Lands' End - Blue - 16 32
    Lands' End
    $42.50
    Tommy Hilfiger Men's Dress Shirt Regular Fit Essentials
    Amazon.com
    Free shipping
    $42.50
    Tommy Hilfiger Men's Dress Shirt Regular Fit Essentials
    Amazon.com
    $35.95
    Men's Long Sleeve Tailored Straight Collar Broadcloth Dress Shirt - Lands' End - Blue - 15H35
    Lands' End
    $35.95
    Men's Long Sleeve Tailored Straight Collar Broadcloth Dress Shirt - Lands' End - Blue - 15H35
    Lands' End
    $44.97
    $74.95
    Men's Tailored Fit No Iron Solid Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Blue - 15 34
    Lands' End
    39% off
    $44.97
    $74.95
    Men's Tailored Fit No Iron Solid Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Blue - 15 34
    Lands' End
    $30.27
    Van Heusen Men's Pinpoint Regular Fit Solid Button Down Collar Dress Shirt
    Amazon.com
    2K+
    $30.27
    Van Heusen Men's Pinpoint Regular Fit Solid Button Down Collar Dress Shirt
    Amazon.com
    $19.99
    Men's Traveler Collection Tailored Fit Spread Collar Check Dress Shirt Clearance At Jos. A. Bank, Blue/Cream/White, Size 17 X 34/35
    Jos. A. Bank Clothiers, Inc.
    $19.99
    Men's Traveler Collection Tailored Fit Spread Collar Check Dress Shirt Clearance At Jos. A. Bank, Blue/Cream/White, Size 17 X 34/35
    Jos. A. Bank Clothiers, Inc.
    $44.97
    $74.95
    Men's Tailored Fit No Iron Solid Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Blue - 17 33
    Lands' End
    39% off
    $44.97
    $74.95
    Men's Tailored Fit No Iron Solid Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Blue - 17 33
    Lands' End
    $26.07
    Van Heusen Men's Dress Shirts Short Sleeve Oxford Solid
    Amazon.com
    3K+
    $26.07
    Van Heusen Men's Dress Shirts Short Sleeve Oxford Solid
    Amazon.com
    $41.97
    $69.95
    Men's Tall Tailored Fit No Iron Solid Supima Cotton Oxford Dress Shirt - Lands' End - Blue - 16H37
    Lands' End
    39% off
    $41.97
    $69.95
    Men's Tall Tailored Fit No Iron Solid Supima Cotton Oxford Dress Shirt - Lands' End - Blue - 16H37
    Lands' End
    $38.31
    STACY ADAMS Men's Regular Fit Big & Tall Solid Dress Shirt
    Amazon.com
    1K+
    Free shipping
    $38.31
    STACY ADAMS Men's Regular Fit Big & Tall Solid Dress Shirt
    Amazon.com
    $47.99
    Neil Allyn Tuxedo Shirt 100% Cotton With Laydown Collar And French Cuffs
    Amazon.com
    693
    Free shipping
    $47.99
    Neil Allyn Tuxedo Shirt 100% Cotton With Laydown Collar And French Cuffs
    Amazon.com
    $25.19
    Alimens & Gentle French Cuff Regular Fit Dress Shirts (Cufflink Included) White New 17.5" Neck 36" Sleeve
    Amazon.com
    11K+
    $25.19
    Alimens & Gentle French Cuff Regular Fit Dress Shirts (Cufflink Included) White New 17.5" Neck 36" Sleeve
    Amazon.com
    $41.97
    $69.95
    Men's Tall Tailored Fit No Iron Twill Long Sleeve Shirt - Lands' End - White - XL
    Lands' End
    39% off
    $41.97
    $69.95
    Men's Tall Tailored Fit No Iron Twill Long Sleeve Shirt - Lands' End - White - XL
    Lands' End
    $19.99
    Van Heusen Men's Dress Shirt Fitted Poplin Solid White 18.5" Neck 36"-37" Sleeve
    Amazon.com
    21K+
    $19.99
    Van Heusen Men's Dress Shirt Fitted Poplin Solid White 18.5" Neck 36"-37" Sleeve
    Amazon.com
    $19.99
    Men's Jos. A. Bank Tailored Fit Spread Collar Mini Gingham Dress Shirt Clearance At Jos. A. Bank, Blue/Navy, Size 14 1 /2 X 32/33
    Jos. A. Bank Clothiers, Inc.
    $19.99
    Men's Jos. A. Bank Tailored Fit Spread Collar Mini Gingham Dress Shirt Clearance At Jos. A. Bank, Blue/Navy, Size 14 1 /2 X 32/33
    Jos. A. Bank Clothiers, Inc.
    $44.97
    $74.95
    Men's Tailored Fit No Iron Pattern Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Orange - 16 33
    Lands' End
    39% off
    $44.97
    $74.95
    Men's Tailored Fit No Iron Pattern Supima Cotton Pinpoint Buttondown Collar Dress Shirt - Lands' End - Orange - 16 33
    Lands' End

    • Tailored Shirts - Men's Dress & Formal Shirts

      Charles Tyrwhitt Shirts
      https://www.charlestyrwhitt.com
      SponsoredShop the latest shirts from Charles Tyrwhitt with a 6-month promise on all orders. Shop shirts from $39.95, available in a range of colours and fits.

      Monogram your Shirt · Shirts From $39.95 · Shirt For All Occasions

      4.5/5 (7,371 reviews)