Men's Nautically Inspired Apparel: Classic styles from boutique brands

Set sail with our men's nautically inspired apparel collections featuring our own signature classic styles and collections from boutique brands caught adrift.

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  • 1776 Seersucker Whaler Shorts

    Show your American pride in our red, white, and blue seersucker shorts. These shorts are made in our Whaler Fit - slightly slimmer fitting shorts that eliminte the back droop found in many men's shorts. These shorts are made in the USA, to ensure the highest quality, from 100% cotton seersucker. To give an extra unique touch, we used wood buttons on the front closure and hook-and-loop back pockets. The final detail is the pocket lining and we've left that decision up to you. Choose from our Nautical Living plaid print or our American the Beautiful flag print. Learn More
  • Bold Red Whaler Shorts

    Be bold in our bright red shorts. These soft, brushed twill shorts are made from 6.5 ounce 100% cotton fabric in a bright red color. Our Whaler fit features an 8.5" inseam, leaving them just above the knee. We've included unique details such as a wood button front closure, brass zipper, and wood buttons with hook-and-loop closures on the back pockets. You get the final say on the last detail: the pocket linings. Choose from Ship's Ahoy, a fun nautical print, or a Nantucket Map, featuring a nautical chart of Nantucket island. Shorts run a little small around the waist. If you are deciding between sizes, we recommend ordering a size up. Made in the USA in a small batch to ensure the highest quality. Learn More
  • Foggy Blue Whaler Shorts

    Soon to be your favorite shorts, these soft, brushed twill shorts are made from 6.5 ounce 100% cotton fabric in a dark gray-blue color. Our Whaler fit features an 8.5" inseam, leaving them just above the knee. We've included unique details such as a wood button front closure, brass zipper, and wood buttons with hook-and-loop closures on the back pockets. You get the final say on the last detail: the pocket linings. Choose from 1776 Seersucker, a red, white, and blue seersucker, or a Nantucket Map, featuring a nautical chart of Nantucket island. Shorts run a little small around the waist. If you are deciding between sizes, we recommend ordering a size up. Made in the USA in small batches to ensure the highest quality. Learn More
  • Khaki Men's Flat Front Cotton Twill Shorts

    100% brushed cotton twill shorts. These khaki men's flat front shorts are very soft and get better with every wash. Solid colorful shorts feature 2 side pockets and 2 buttoned back pockets. Flat front with 9 inch nseam and zippered fly. Available for sale in an assortment of colors. Learn More
  • Light Bluefish Whaler Shorts

    Our Light Bluefish shorts are made from 8.5 ounce 100% cotton and come in our exclusive Whaler Fit. Featuring an 8.5" inseam, these light blue shorts fall just above the knee. We've included some great details like a wooden front button closure, brass zipper, and matching wooden buttons with hook-and-loop closures above the back pockets. The final detail is up to you: Choose between a Nantucket Map print, featuring a nautical chart of Nantucket, and Ship's Ahoy, a fun nautical print. Made in the USA in a small batch to ensure the highest quality. These are running a bit small so if you're deciding between sizes, we recommend ordering one size up. Learn More
  • Men's Whaler Shorts - Marblehead Madras (Green)

    Though we don't condone whaling, our Whaler Shorts are perfect for almost every other summer activity. Made in the USA from 100% cotton patchwork madras. Our Marblehead Madras is true patchwowrk madras with various plaids hand stitched together. Great fitting shorts without much extra "droop" in the back. 9" inseam. Button front with zipper fly. Two back pockets. Machine wash. Learn More
  • Men's Whaler Shorts - Red Oxford

    Though we don't condone whaling, our Whaler Shorts are perfect for almost every other summer activity. Made in the USA from 100% cotton oxford. Our red oxford has a unique distressed look. Great fitting shorts without much extra "droop" in the back. 9" inseam. Button front with zipper fly. Two back pockets. Machine wash. Learn More
  • Men's Whaler Shorts in Blue Check Seersucker

    Seersucker shorts are a classic staple of the American man’s summer wardrobe. We grew up running (and sailing) around in seersucker and still wear it to this day.  It’s breathable, cool, and perfect for warm weather. 

    Although we love seersucker, we didn’t love the fit of most of the seersucker shorts available. Typically, they’re too baggy and boxy. Occasionally they’re way too short.  We’ve spent the last few years perfecting the fit of our shorts are are proud to offer our Whaler Shorts: great fitting men’s shorts with attention to all the details.

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  • Navy Men's Flat Front Cotton Twill Shorts

    100% brushed cotton twill shorts. These navy men's flat front shorts are very soft and get better with every wash. Solid colorful shorts feature 2 side pockets and 2 buttoned back pockets. Flat front with 9 inch nseam and zippered fly. Available for sale in an assortment of colors. Learn More
  • Stone Men's Flat Front Cotton Twill Shorts

    100% brushed cotton twill shorts. These stone men's flat front shorts are very soft and get better with every wash. Solid colorful shorts feature 2 side pockets and 2 buttoned back pockets. Flat front with 9 inch nseam and zippered fly. Available for sale in an assortment of colors. Learn More
  • White Men's Flat Front Cotton Twill Shorts

    100% brushed cotton twill shorts. These white men's flat front shorts are very soft and get better with every wash. Solid colorful shorts feature 2 side pockets and 2 buttoned back pockets. Flat front with 9 inch nseam and zippered fly. Available for sale in an assortment of colors. Learn More

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