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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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LAVELLE DRESS PANT 022326
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LAVELLE DRESS PANT 022326

$228.00
$228.00
HALYARD SHORT SLEEVE 060525
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HALYARD SHORT SLEEVE 060525

$118.00
$118.00
VERSA POLO 041125
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VERSA POLO 041125

$29.99
$29.99 $98.00
LAVELLE BLAZER 022326
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LAVELLE BLAZER 022326

$498.00
$498.00
HERITAGE SWEATER 100925
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HERITAGE SWEATER 100925

$168.00
$168.00
WATSON FLANNEL SUIT PANT 110624
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WATSON FLANNEL SUIT PANT 110624

$49.99
$49.99 $168.00
VERSA SS POLO 033126
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VERSA SS POLO 033126

$108.00
$108.00
WATSON FLANNEL SUIT JACKET 110624
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WATSON FLANNEL SUIT JACKET 110624

$288.00
$288.00
NEWPORT SHORT SLEEVE 051226
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NEWPORT SHORT SLEEVE 051226

$138.00
$138.00
LEEWARD DRESS SHIRT 022326
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LEEWARD DRESS SHIRT 022326

$158.00
$158.00
BRENTWOOD VEST 100925
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BRENTWOOD VEST 100925

$268.00
$268.00
NORTHWOOD VEST 091125
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NORTHWOOD VEST 091125

$238.00
$238.00