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 No Tuck Regular Tall 30L 32L 34L Apply Filters Sort by: Featured Best Selling Price - Low to High Price - High to Low Leeward Dress Shirt Cream Caribou Plaid $109 $138 Quick View Helmsman 5 Pocket Pant Walnut Solid $109 $138 Quick View Leeward Dress Shirt Maritime Blue Geo Print $109 $138 Quick View Helmsman 5 Pocket Pant Black Solid $138 Quick View Leeward Dress Shirt Large Burgundy Plaid $79 $138 Quick View Helmsman 5 Pocket Pant Deep Ocean Solid $109 $138 Quick View Leeward Dress Shirt Navy Aqua Gingham $109 $138 Quick View Leeward Dress Shirt Navy Dot Print $138 Quick View Leeward Dress Shirt Gray Floral Dot Print $99 $138 Quick View Helmsman 5 Pocket Pant Burgundy Solid $109 $138 Quick View Leeward Dress Shirt Corner Pocket Print $79 $138 Quick View Helmsman 5 Pocket Pant Olive Solid $109 $138 Quick View Leeward Dress Shirt Blue Gold Plaid $99 $138 Quick View Leeward Dress Shirt Ctrl+Alt+Delete Print $99 $138 Quick View Helmsman 5 Pocket Pant Charcoal Solid $138 Quick View Leeward Dress Shirt Navy Multi Check $138 Quick View Leeward Dress Shirt Light Blue Navy Mini Grid $138 Quick View Leeward Dress Shirt Navy Pink Dot Print $99 $138 Quick View Leeward Dress Shirt Pink Gray Diamond Print $99 $138 Quick View Leeward Dress Shirt Blue Tonal Check $99 $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 $128 $138 Quick View Helmsman 5 Pocket Pant Moonlight Blue Solid $99 $128 Quick View Leeward Dress Shirt Light Blue Solid $128 Quick View Helmsman Chino Pant Navy Solid $138 Quick View Leeward Dress Shirt White Navy Windowpane $138 Quick View Leeward Dress Shirt Blueprint Gingham $109 $138 Quick View Leeward Dress Shirt Quiet Harbor Plaid $109 $138 Quick View Leeward Dress Shirt Blue Rose Dot Print $109 $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 $138 Quick View Leeward Dress Shirt Provence Plaid $138 Quick View Leeward Dress Shirt Bright White Multi Plaid $138 Quick View Leeward Dress Shirt Provence Multi Plaid $138 Quick View Leeward Dress Shirt Set Sail Ipanema Star Print $138 Quick View Leeward Dress Shirt Capri Breeze Floral Print $138 Quick View Leeward Dress Shirt Prairie Sunset Plaid $138 Quick View Leeward Dress Shirt Ashley Blue Plaid $138 Quick View Leeward Dress Shirt Ashley Blue Multi Plaid $138 Quick View Leeward Dress Shirt Prairie Sunset Multi Plaid $138 Quick View Leeward Dress Shirt White Multi Plaid $138 Quick View Leeward Dress Shirt Micro Chip Diamond Print $138 Quick View