For more Prime Day menswear deals—including these Calvin Klein skivvies—start here. For every other worthwhile bargain we’ve found, check our ongoing master list of the best Prime Day Deals so far.


You can’t talk about underwear without talking about Calvin Klein underwear. The brand’s genre-defining boxer briefs tend to dominate our rankings for good reason: when CK introduced them in the early ’80s, they made designer underwear a thing, ushering in the era of the celebrity campaign in the process. 40-odd years after their debut, Calvin Klein’s skivvies still set the standard. The brand might enlist everyone from Jeremy Allen White to Jeremy Pope to hawk ‘em, but they look just as great on Average Joes in need of a jolt of confidence.

In 2025, that cohort of “Average Joes” includes no shortage of friendly neighborhood GQ editors: In our latest round of testing, Calvin Klein underwear scored expectedly high marks across the board. According to the Recommends squad, CK’s cotton-stretch undies are as good-looking as they are comfortable. The fabric comes imbued with just the right amount of stretch, solid support in the pouch, and more breathability than most of its counterparts, a major win for the old guard.

Calvin Klein

Cotton Stretch Boxer Brief (3-Pack)

Calvin Klein

Cotton Classics Boxer Brief (3-Pack)

Crucially, they’re not prone to chafing or riding up, a welcome boon for GQ’s notable-but-anonymous low-rise devotees. There’s also the little fact that they’ll make you feel hot enough to front your own billboard campaign, an unusual perk we really can’t emphasize enough.

Here’s the real kicker, though: right now, all of that pouch-supporting, anti-chafing, billboard-fronting goodness is cheaper than we’ve ever seen it. Under normal circumstances, a pack of three briefs would run you about $48—today, thanks to Amazon Prime Day, they’ll only cost you $24. Math was never our strong suit, but the pencil-pushers in GQ’s finance department tell us that’s roughly…eight bucks per pair.

You are, of course, free to do with that information as you will. But if you’ve been waiting for a miraculous sign of fashion kismet to overhaul your underwear drawer (and the holes in your briefs weren’t enough), here it is. Calvin Klein’s entire oeuvre of undies—boxer briefs, low-rise trunks, briefs briefs—is on a pinch-me sale at this very moment, and you won’t find a better reason to ixnay those ratty no-name skivvies than that.

Calvin Klein

Cotton Stretch Low Rise Trunk (3-Pack)

Calvin Klein

Cotton Classics Brief (3-Pack)


Prime Day FAQ

What are the best menswear brands on Amazon?

For affordable fashion across the board, Amazon’s got the goods. If you’re after basics, look to tried-and-true labels like Gildan, Calvin Klein, Russell Athletic, and Kirkland Signature. On the footwear front, you’ll find everything from Adidas sneakers to Red Wing boots to Allen Edmonds dress shoes. The watch selection is equally stacked, with classics from Casio, G-Shock, Seiko, and even the occasional Tag Heuer. And when it comes to sunglasses on Amazon, don’t sleep on Ray-Ban, Chimi, and Oakley. With more and more inventory from Shopbop (Amazon’s fashion-focused subsidiary) making its way onto the platform, Amazon’s menswear lineup is deeper than you’d expect.

Do I need to be a Prime member to shop Amazon Prime Day?

Bad news on that front: You definitely need a Prime membership to avail yourself of the deals. (They get us all in the end, huh?) If you made it this far without signing up 1) Kudos! 2) Where do you panic-order your toilet paper? 3) You’ll probably be okay without a membership going forward. If you’re desperate to get in on the Prime Day cologne deals, you can sign up for a 30-day free trial here.

How long do the deals last?

For as long as we can remember, Prime Day has been a two-day event. Not this year. In 2025, you’ll have four full days to shop the breadth of Amazon’s discounts, which begin the morning of July 8 and end the evening of July 11.

Do Prime Day deals change each day?

Yes, Prime Day deals definitely change each day, sometimes even by the hour. Amazon rotates in new discounts across all categories (tech, clothing, home, you name it), so what’s here today might be gone tomorrow. Some deals only last 24 hours, and others sell out even faster. If you see something you like, it’s probably smart to grab it before it’s gone.

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