Leeward and Helmsman Edit Filters Filter Your Shop Color All Colors Black Blue Green Purple Yellow Red Orange White Gray Pink Size All Sizes X-Small Small Medium Large X-Large XX-Large 3X-Large 30W 32W 34W 36W 38W 40W Fit All Fits Trim Classic Length All Lengths Regular Tall 30L 32L 34L Apply Filters Sort by: Featured Best Selling Price - Low to High Price - High to Low Helmsman 5 Pocket Pant Walnut Solid $109 $138 Quick View Leeward Dress Shirt Light Blue Mini Plaid $138 Quick View Helmsman 5 Pocket Pant Black Solid $138 Quick View Leeward Dress Shirt Plum Gray Dot Print $138 Quick View Helmsman 5 Pocket Pant Deep Ocean Solid $109 $138 Quick View Helmsman 5 Pocket Pant Burgundy Solid $109 $138 Quick View Helmsman 5 Pocket Pant Charcoal Solid $138 Quick View Leeward Dress Shirt White Solid $138 Quick View Leeward Dress Shirt Light Blue Solid $138 Quick View Leeward Dress Shirt Black Solid $138 Quick View Leeward Dress Shirt Light Blue Gingham $138 Quick View Leeward Dress Shirt White Navy Mini Grid $138 Quick View Leeward Dress Shirt Light Blue Gingham $99 $128 Quick View Helmsman 5 Pocket Pant Moonlight Blue Solid $99 $128 Quick View Helmsman 5 Pocket Pant Deep Sage Solid $89 $128 Quick View Helmsman 5 Pocket Pant Navy Solid $89 $128 Quick View Helmsman Chino Pant Navy Solid $138 Quick View Leeward Dress Shirt White Navy Windowpane $138 Quick View Helmsman 5 Pocket Pant Navy Solid $138 Quick View Helmsman 5 Pocket Pant Hummus Solid $138 Quick View Leeward Dress Shirt Nightshade Windowpane $99 $138 Quick View Leeward Dress Shirt Provence Plaid $99 $138 Quick View Leeward Dress Shirt Bright White Multi Plaid $99 $138 Quick View Leeward Dress Shirt Provence Multi Plaid $99 $138 Quick View Leeward Dress Shirt Set Sail Ipanema Star Print $99 $138 Quick View Leeward Dress Shirt Capri Breeze Floral Print $99 $138 Quick View Leeward Dress Shirt Prairie Sunset Plaid $99 $138 Quick View Leeward Dress Shirt Ashley Blue Plaid $99 $138 Quick View Leeward Dress Shirt Ashley Blue Multi Plaid $99 $138 Quick View Leeward Dress Shirt Prairie Sunset Multi Plaid $99 $138 Quick View Leeward Dress Shirt White Multi Plaid $99 $138 Quick View Leeward Dress Shirt Micro Chip Diamond Print $99 $138 Quick View Leeward Dress Shirt Lotus Windowpane $119 $138 Quick View Leeward Dress Shirt White Windowpane $119 $138 Quick View Leeward Dress Shirt Skyway Circle Geo Print $119 $138 Quick View Leeward Dress Shirt Deep Sea Multi Plaid $119 $138 Quick View Leeward Dress Shirt Deep Ocean Multi Dot Print $99 $138 Quick View Leeward Dress Shirt Navy Madison Check $119 $138 Quick View Leeward Dress Shirt Navy Solid $138 Quick View Leeward Dress Shirt Navy Montgomery Plaid $119 $138 Quick View Leeward Dress Shirt Sky Ludlow Plaid $119 $138 Quick View Leeward Dress Shirt Navy Ludlow Plaid $138 Quick View Leeward Dress Shirt Sky Hampton Plaid $138 Quick View Leeward Dress Shirt Navy Dash Repeat $119 $138 Quick View Leeward Dress Shirt Deep Sea Oaklawn Plaid $119 $138 Quick View Leeward Dress Shirt Deep Sea Plus Print $119 $138 Quick View Helmsman 5 Pocket Pant Khaki Solid $138 Quick View Leeward Dress Shirt White Manor Plaid $138 Quick View Leeward Dress Shirt White Linear Triangle $119 $138 Quick View Leeward Dress Shirt Black Dallas Plaid $119 $138 Quick View Leeward Dress Shirt Garnet Gingham $119 $138 Quick View Leeward Dress Shirt White Pong Print $138 Quick View Leeward Dress Shirt Sage Lexington Plaid $138 Quick View Leeward Dress Shirt Navy Lexington Plaid $138 Quick View Leeward Dress Shirt White Hebron Plaid $138 Quick View Leeward Dress Shirt Sage Dot $138 Quick View Leeward Dress Shirt Sage Multi Gingham $138 Quick View