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Prime Day Is Coming—These 56% Off Menswear Deals Are Already Live

Prime Day Is Coming—These 56% Off Menswear Deals Are Already Live

Posted on September 29, 2026

“Hearst Magazines and Yahoo may earn commission or revenue on some items through these links.”

Quick Overview

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FALL HAS A way of making us want to sit down, grab our phones and start scrolling for new clothes. Maybe it’s the first hint of sweater weather or maybe it’s simply the fact that Prime Day is around the corner. Whatever the reason, October 6 and 7 are shaping up to be a pretty good excuse to finally buy the pieces you’ve had your eye on or upgrade the ones in your closet that have seen better days.

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As Men’s Health fashion editors, we spend a lot of time looking at menswear, which means we know a good deal when we see one. Ahead of Prime Day, we’ve combed through countless discounts to find the ones worth your attention, filtering out the forgettable markdowns and zeroing in on clothes and shoes that bring something to the table beyond a tempting price tag. Whether you’re gearing up for chillier temps with a new cardigan or crewneck, looking for a pair of rain jacket to beat the elements, or need a white dress shirt or blazer for the office, there’s plenty to shop right now. We spotted deals from menswear brands including Carhartt, The North Face, Levi’s and more, with select picks marked down by as much as 56 percent.

Dockers Straight Fit Workday Khaki Smart 360 Flex Pants

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Courtesy of Retailer

Coofandy Long Sleeve Lightweight Pullover Sweater

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Courtesy of Retailer

Columbia Watertight II Rain Jacket

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Courtesy of Retailer

Carhartt Iconic J01 Duck Detroit Jacket

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Courtesy of Retailer

Levi’s 505 Regular Fit Jeans

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Courtesy of Retailer

The North Face Aconcagua 3 Hooded Jacket

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Calvin Klein Straight High Stretch Jeans

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Amazon Essentials Relaxed-Fit Cotton Blend Cardigan

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Courtesy of Retailer

Tommy Hilfiger Short Sleeve Striped Cotton Crewneck Graphic T-Shirt

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adidas Microfiber Boxer Briefs (3-Pack)

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PJ Paul Jones Lightweight Sport Coat Slim Fit

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Courtesy of Retailer

Nike Men’s Club Cuffed Brushed Fleece Pants

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Under Armour Tech Golf Polo

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Bruno Marc KnitFlex Breeze Casual Dress Sneakers

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G Gradual Athletic Pants

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Fall is my favorite season to get dressed and I’m a sucker for a good sweater, especially one that looks more expensive than it actually is. For example, this Long Sleeve Lightweight Pullover Sweater from Coofandy feels like it should cost twice the amount. It’s made from premium-like polyester fabric and has a slim fit that’s flattering without feeling tight. I can easily layer it over a button-down without bunching and wear it with a nice pair of slacks and dress sneakers for work. It also comes in a number of different colors, so you can stock up for one every day of the week.

Speaking of dress sneakers, Bruno Marc makes some of my favorite affordable options for business-casual outfits. Take the KnitFlex Breeze Casual Dress Sneakers. They have a breathable knit upper and a foam insole designed to help manage moisture and keep your feet feeling fresh. More importantly, they really feel like sneakers. There’s enough cushioning and support to wear them comfortably on those extra-long workdays when our photo shoots stretch past eight hours.

If you’re looking for a pair of workout pants that can keep up with your training sessions, G Gradual has a pair currently marked down 20 percent. Since they’re super comfortable with a clean aesthetic, you can also reserve them for travel days or quick errands. For the basics drawer, Adidas has micro boxer briefs that are especially well-suited for workouts and training. They’re soft and stretchy, and the quick-drying fabric helps keep sweat from lingering against your skin.

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Amazon Prime Day officially kicks off October 6 and 7, but you don’t necessarily have to wait until then to start shopping. These deals are already live, and if you see something you like, it may be worth grabbing it before the full Prime Day shopping frenzy begins and popular sizes and colors start disappearing.

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