A Field Guide to Preppy Summer Pants

Whale pants or Nantucket reds?

In terms of fashionableness, festive pants are a special breed: both never out of style, yet never quite in it. But, of course, as with their kin, the conversational tie, fashion isn’t quite the point. Although it’s counterintuitive to think that primary colors or kitten embroidery could be a way for grown men to prove their worth, truly nothing says, “I summer on an island,” like a guy in floral pants. Because unless his mom is still dressing him, there is literally no other reason he would own them.

At the same time, festive pants are an unlikely equalizer: no matter your body type or beer gut, no one really looks good in them. As such, they are not without controversy.

“I personally think ‘pant parties’ are a no-no, unless they’re an intentional inside joke amongst like minds,” says Kate Schelter, author of the new Classic Style (Grand Central Life & Style), an illustrated guide to everyday classics, featuring a foreword by Andy Spade. “In any case, they’re kind of like flip flops—you ought to be able to see the water or feel it between your toes when you wear them.”


Should you see such a pair in the wild, use this guide to tell what sort of party you’re about to encounter.

Nantucket Reds

The pants that spawned a genre, for better or worse.

The original Nantucket Reds were created in the 1960s by Nantucket retailer Philip Murray, and, if you’re lucky, yours are that old. That’s because Reds get better with age. Schelter calls them “the Levis of cocktail pants. When worn-in and worn properly, they make a statement subtly.” Best paired with a gray tee, but 9 out of 10 will opt for a button-down, blazer, and baseball cap (front-facing, fingers crossed).

Who wears them: 3rd generation Nantucketers, finance guys on vacation

On: Nantucket

While drinking: Whale’s Tale, from the can

Nantucket Reds Plain Front Pants, $94.50 (P4,793.51)

Madras Trousers

A more acceptable counterpart to the seersucker; usually patchwork.

Like the Reds, there’s status in owning a beat-up pair. “For some, it’s a life-long pursuit to perfectly crease pants into the mold of one’s body,” says Schelter. “Others hasten the act by dunking it in salt water and leaving it on the line to dry—all summer.” Also spotted in jacket form. Wear together at your own risk.


Who wears them: fashion boys, sons-in-law, finance guys on vacation

On: Bermuda

While drinking: Rum punch

Madras Trousers, J.Press, $108.75 (P5,516.34)


Whale pants. Not for everyday use. @ritzcarlton

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Also called “club pants” (while holding, while at).

What began as Lacoste’s simple embroidered alligator has evolved—too far one might argue—into all-over embroidery in motifs as wildly off-brand as beer and pretzels. Also: lobsters, martinis, Santas.

In a 1976 article for Esquire, Tom Wolfe famously coined the examples he saw Bostonians wearing on Martha’s Vineyard as “go to hell” pants. Schelter thinks they look “kind of canned and cartoonish.”

Who wears them: suburban soccer dads, ad guys on vacation

On: Martha’s Vineyard

While drinking: Moscow Mules

Harbor Seersucker Pant with Lobsters, $114 (P5,782.65)


Seersucker: not just for horse races anymore. (Shop via link in bio.)

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Flattering on virtually no one, not to mention single-use only if you’re even a slightly sloppy buzz.

This classic has roots in colonial India, though eventually evolved into pants capable of imparting a look that could “cash a check with no questions asked.”


Today, a man in seersuckers sits firmly on the line between clean cut coed with a decent sense of humor and bad-intentioned frat boy with none. Blue is the most popular, but real men prefer pink.

Who wears them: hipsters, creepy uncles, Prince George

In: The Hamptons

While drinking: G&Ts

Ludlow suit pant in Japanese seersucker, $158 (P8,014.55)

Khaki, Pleated

Appealingly nerdy, nostalgically Obama; leaves room for ice cream after the lobster roll.

Their status is in their frugality. As Schelter writes in Classic Style, “Yankees don’t believe in buying fancy new clothes, because the clothes they buy are investments that ought to last from college to the grave. You keep the same clothes for decades because they don’t go out of style—style is irrelevant if they function and perform… Worn-in is the look, the unspoken code, the working key that unlocks the definition of classic character.”


Who wears them: The whole family

On: Mount Desert Island

While drinking: Glenlivet with a PBR chaser; Chardonnay for the lady

Ralph Lauren Slim Fit Cotton Twill Pant, $125 (P6,340.63)

This story originally appeared on
* Minor edits have been made by the editors.

Prices are based on the conversion rate of $1 = P50.73.

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Alyssa Giacobbe
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