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The Origin Story

At the sight of a sweat-drenched D.C. staffer running into a meeting, the same thought that sparked a democracy also rattled around in our founder’s head: there has to be a better way. That better way was the Leeward. The best damn dress shirt.

It all starts with the fabric.

No one (and we mean no one) makes a better performance dress shirt. By combining the perfect blend of fibers with modern silhouettes, we’ve created clothes that look great and feel even better. Imagine wearing your favorite athletic wear to work. That’s what our dress shirts are like.
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HELMSMAN SHORTS 032425
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HELMSMAN SHORTS 032425

$29.99
$29.99 $98.00
BRAIDED BELT
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BRAIDED BELT

$78.00
$78.00
FRESCO SLIM SUIT PANT 041524
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FRESCO SLIM SUIT PANT 041524

$278.00
$278.00
HALYARD DRESS SHIRT 022326
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HALYARD DRESS SHIRT 022326

$148.00
$148.00
CITY FLANNEL PLAID 110624
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CITY FLANNEL PLAID 110624

$148.00
$148.00
FRESCO SLIM SUIT JACKET 041524
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FRESCO SLIM SUIT JACKET 041524

$598.00
$598.00
BATEMAN DRESS SHIRT 110624
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BATEMAN DRESS SHIRT 110624

$158.00
$158.00
MONACO DRESS SHIRT 0424
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MONACO DRESS SHIRT 0424

$138.00
$138.00
LEEWARD LS DRESS SHIRT 0424
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LEEWARD LS DRESS SHIRT 0424

$138.00
$138.00
HALYARD SS SHIRT 050526
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HALYARD SS SHIRT 050526

$118.00
$118.00
LEEWARD SHORT SLEEVE 041125
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LEEWARD SHORT SLEEVE 041125

$118.00
$118.00
LEEWARD DRESS SHIRT 041125
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LEEWARD DRESS SHIRT 041125

$138.00
$138.00