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Calvin Klein underwear hits 60% off for fall Prime Day

By Frenzee Editorial · Oct 6

Rewritten from reporting by Esquire. Read the original at https://www.esquire.com/style/a74053168/calvin-klein-underwear-prime-day-deals (opens in a new tab). Esquire first published it on 6 Oct 2026.

Esquire's commerce team calls the classic cotton boxer briefs the one practical buy worth making during Amazon's sale event.

Amazon Prime Day may tempt shoppers with Apple gadgets and luxury fragrances, but the most worthwhile purchases tend toward the practical. Underwear tops that list, and Calvin Klein currently dominates the category with discounts reaching 60 percent.

Bryn Gelbart, associate commerce editor at Esquire, credits the brand's classic cotton boxer briefs with ending his reliance on cheaper alternatives. In his review, he describes them as "supremely comfortable" rather than merely hassle-free. He notes the design provides ample room while maintaining structural support, and praises the elastic for staying in place without constriction. The breathability makes them his preferred choice for travel.

"If all my Calvins are in the hamper, I know I'm in for a tough day," Gelbart says.

The sale extends beyond boxer briefs to include trunks, boxers, and briefs at the same discount level. Socks and undershirts from the brand are also reduced.

The author, who monitors deals year-round, describes these prices as exceptional and notes having shared links with family members immediately upon discovery.