For more Prime Day menswear deals—including these Dockers pants—start here. For every other worthwhile bargain we’ve found, check our ongoing master list of the best Prime Day Deals so far.
Last Updated 7/9/2025 at 10:11 a.m. ET: If you haven’t heard of Dockers, the ‘80s-born label with a particular knack for khaki, we know at least one guy in your life who has: your dad, who probably owns a collection of them that predates you. He’s not the only one—for as long as Dockers has been in the khaki business, it’s endeared itself to dads, the sole demographic in the khaki business that really matters. Don’t believe us? Crack open your old man’s closet and take a gander. If the khakis hanging in there aren’t from Dockers, we’ll give you a dollar. And if they are, we’ll give you roughly 34 more, so you can hightail it to Amazon, where they’re currently on sale, and buy your very own pair.
Surprised to hear us recommend pants your pops swears by? You shouldn’t be. In fact, their righteous, anti-fashion dadliness is a big part of their appeal, and a huge part of what makes the khaki wizards at Dockers an utterly predictable source of some of the best pants we’ve clocked on sale this Prime Day—or any other day, really.
While other brands have busied themselves with introducing lycra-enhanced chinos and elastic-waist trousers, Dockers has consistently produced bangin’ khakis worth every meager buck. Sure, these days its assortment includes a contemporary-leaning slim fit or two, some of them equipped with a touch of stretch or salsa-dodging stain-repellent—evidence that Dockers cares about dads and real dudes in equal measure. But for our money, the brand’s bread and butter remains the classic khakis your dad loves, cut with a relaxed fit, higher rise, and at least one crisp pleat.
It’s at this point, of course, that the various colleagues we’ve badgered with our well-rehearsed Dockers spiel tend to lose interest. Totally, they might say, while their eyes scan the room for somebody, anybody, to spare them the indignity of hearing the words “double-pleated” for the sixteenth time in as many seconds. We get it—some of you are visual learners. So to help strengthen our case, we ordered a pair of Dockers straight from the source and passed ’em around the GQ offices for honest appraisal.
“Ah, shit,” grumbled GQ senior commerce editor Avidan Grossman when he first tried on the brand’s signature relaxed-fit pleated khakis. “These are good.” Grossman is more persnickety about pants than most folks are haircuts, and it took him all of a minute to begrudgingly concede Dockers’ $50 khakis looked as good as a vintage pair he bought for quadruple the price. He likened the silhouette—loose through the thigh, with a classic straight leg—to J.Crew’s GQ-favorite chinos, with the bonus addition of two pleats and a slightly longer inseam, retro flourishes that honor the khaki’s military origins.
At $50 on most days—and $35 on Prime Day—these might be the best bang-for-your-buck khakis on the market. The only problem? Once your dad catches wind of the deal, he’s liable to beat you to it. So if you still haven’t figured out an appropriate way to thank him for years of Dockers-clad child-rearing, we’ve got a wonderful suggestion: make your way to Amazon, secure a pair in your size, and then forward the link his way.
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. And 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?
Yep, Prime Day deals definitely change each day, and sometimes even by the hour. Amazon rotates in new discounts each day 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 with a quickness. If you see something you like, it’s probably smart to grab it before it’s gone.
