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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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HALYARD SHORT SLEEVE 022326
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HALYARD SHORT SLEEVE 022326

$118.00
$118.00
CITY PLAID FLANNEL 110725
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CITY PLAID FLANNEL 110725

$148.00
$148.00
LEEWARD NO TUCK SHIRT 060525
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LEEWARD NO TUCK SHIRT 060525

$138.00
$138.00
LEEWARD NO TUCK DRESS SHIRT 021425
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LEEWARD NO TUCK DRESS SHIRT 021425

$138.00
$138.00
LEEWARD SHORT SLEEVE 042826
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LEEWARD SHORT SLEEVE 042826

$128.00
$128.00
KENNEDY NO TUCK SHIRT 033126
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KENNEDY NO TUCK SHIRT 033126

$148.00
$148.00
NEWPORT DRESS SHIRT 051226
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NEWPORT DRESS SHIRT 051226

$168.00
$168.00
LEEWARD SOLID LT BLUE 042826
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LEEWARD SOLID LT BLUE 042826

$158.00
$158.00
HALYARD SHORT SLEEVE 022326
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HALYARD SHORT SLEEVE 022326

$118.00
$118.00
LEEWARD DRESS SHIRT 032425
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LEEWARD DRESS SHIRT 032425

$138.00
$138.00
LEEWARD SHORT SLEEVE 080725
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LEEWARD SHORT SLEEVE 080725

$118.00
$118.00
PALMER T SHIRT 051226
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PALMER T SHIRT 051226

$68.00
$68.00