Nautically-inspired goods from boutique brands for him, her & home

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Men's Preppy Shorts | Madras And Seersucker Shorts

Shorts are a staple in every man's spring and summer wardrobe, and our collection of preppy styles includes a variety of different fits and fabrics to suit every occasion. Available in flat front designs and relaxed silhouettes, this collection features our signature Whaler Fit in colorful seersucker stripes, vibrant madras plaids, crisp cotton twill, and other lightweight fabrics that make them perfect for warm weather. Detailed with functional pockets, belt loops, clean lines, and high-quality zippers and buttons, many of our men's shorts are made right here in the USA. Our shorts include novelty pocket linings that add an extra special touch, high-quality craftsmanship that gives them a crisp, clean look, and impeccably tailored details that maintain the aesthetic of our Cape Cod heritage. From a morning out at sea to an afternoon on the golf course to dinner by the beach, our men's shorts offer style and comfort that lasts from day to night.

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  • Faded Red Twill Shorts in Whaler Slim Fit

    Detailed with nautically inspired pocket linings that add a unique touch, the Red Faded Twill Shorts in Whaler Slim Fit are amongst our favorite colorful summer styles. Proudly made in the USA from 100% cotton fabric, our Whaler Fit shorts offer all-day comfort, classic style, and a preppy fit with an 8 inch inseam that makes them perfect for any man who loves the Cape Cod lifestyle. The waistband secures with a wooden button and a YKK zipper while the back features two welt pockets with button details and anchor emblems that add our signature nautical touch.

    Pair these shorts with a solid white button down shirt for an outdoor dinner party or a casual event, or wear them with a colorful polo shirt for a day of sailing or watching the boats stream up and down the coast. Belt loops at the waistband offer the option to wear a tucked in shirt with a belt for a crisp, clean, pulled-together look.

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  • Men's Flat Front Cotton Twill Short

    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

    Regular Price: $59.00

    $29.50

  • Men's Flat Front Cotton Twill Short

    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

    Regular Price: $59.00

    $29.50

  • Men's Flat Front Cotton Twill Short

    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

    Regular Price: $59.00

    $29.50

  • Men's Flat Front Cotton Twill Short

    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

    Regular Price: $59.00

    $29.50

  • 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
  • Cisco Madras Whaler Shorts

    Our Whaler Shorts are perfect for almost every summer activity. Made in the USA from 100% cotton patchwork madras. Named for Cisco Beach on Nantucket. Our Cisco Madras is true patchwork 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
  • Marblehead Madras Whaler Shorts

    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
  • Blue Seersucker Shorts

    Stay cool and stylish in our men's blue and white seersucker shorts. Our men's shorts are always some of our most popular items. Shorts feature alternating blue and white stripes in lightweight seersucker. Two slanted side pockets and two buttoned back pockets. Reinforced waistband to prevent curling. 100% cotton seersucker. 9 inch inseam. Learn More

    Regular Price: $65.00

    $37.50

  • 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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  • 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
  • Navy Oxford Shorts in Whaler Slim Fit

    The Navy Oxford Shorts in Whaler Slim Fit offer a classic, preppy look that can be worn for any casual occasion. Detailed with slant front pockets, a wooden button, and a YKK zipper closure, these shorts are designed with distinctive details that add our unique touch. Trimmed with nautical prints in the linings of the pockets, these shorts feature a slim, preppy fit with an 8 inch inseam, belt loops, and back welt pockets with buttons and anchor emblems that add a touch of nautical charm.

    Made in the USA from 100% cotton oxford fabric, these shorts are easy to pair with any top in your warm weather wardrobe. Wear them with a tucked in button front sport shirt and a classic leather belt, pair them with a simple polo shirt and a nautical patterned belt, or team them with a lightweight summer hoodie or a preppy cotton sweater for a look that you can wear on your boat, out to dinner, or to any casual daytime event.

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  • Red Oxford Whaler Shorts

    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