Friday, March 6
  • Amazon officially announced the dates for its fall Prime Day, Prime Big Deal Days.
  • The two-day savings event will take place from October 7 and run through midnight, October 8.
  • We’re already seeing savings on editor-tested products from Apple, Yeti, Brooks, Garmin, and more.

ROUND 2 OF Amazon Prime Day is finally here through tomorrow, and it’s not just for gadgets. This year, men’s wardrobe essentials are getting some of the best markdowns we’ve seen: underwear, undershirts, joggers, jackets, and more. As a Men’s Health style editor who’s covered this shopping event for five seasons, I’ve learned that not all deals are created equal. We don’t just highlight discounts; we actually test the clothes that guys wear day in and day out. That means when we highlight a Prime Day pick, it’s because it’s been vetted for comfort, durability and style—not because it’s something cheap.

Other outlets might hand you a list of the lowest prices, but we focus on value that lasts. Whether you’re upgrading your everyday basics, adding versatile pieces to your rotation, or getting ahead on holiday shopping, our Prime Day coverage shows you exactly what’s worth picking up—and what’s better left behind.

SHOP PRIME DAY MENSWEAR DEALS

Best Shacket

CirrusLite Shirt Jacket

Eddie Bauer CirrusLite Shirt Jacket

Now 42% Off

Most Comfy Underwear

Calvin Klein Micro Stretch 7-Pack Boxer Brief

Now 55% Off

Best Jogger

Under Armour UA Sportstyle Joggers

Now 50% Off

OG Sneaker

Reebok Club C 85 Vintage Sneaker

Now 35% Off

Best Quarterzip

GAP Mens Cashsoft Quarterzip Sweater

Now 15% Off

Best Sweatshirt

Champion Men’s Crewneck, Fleece Sweatshirt

Now 63% Off

Best Sunnies

Ray-Ban RB2140 Original Wayfarer Square Sunglasses

Now 20% Off

Durable Trekker

Eddie Bauer Men’s Athletic Fit Rainier Pants

Now 59% Off

For Dinner

Tommy Hilfiger Chino Pants Stretch Slim-Fit

Now 45% Off

Best Polo

Lacoste Men’s Original Piqué Polo Shirt

Now 43% Off

Coveted Basic

BAMBOO COOL Men’s Undershirts

Now 20% Off

Best Knit Polo

PJ PAUL JONES Knit Polo Shirt

Now 20% Off

Perfect for Dressy Events

Alimens & Gentle Short Sleeve Dress Shirt

Now 22% Off

Best Jacket

John Varvatos Andrew Leather Jacket

Now 30% Off

For the Elements

Amazon Essentials Lightweight Water-Resistant Packable Puffer Vest

Now 24% Off

Best Canvas Jacket

Levi’s Workwear Cotton Canvas Depot Jacket

Now 15% Off

Best Windbreaker

Callaway Long Sleeve Full-Zip Wind Jacket

Now 45% Off

Calvin Klein’s Micro Stretch 7-Pack Boxer Briefs are the ultimate Prime Day stock-up buy because they’re comfortable, supportive, and keep you set for a whole week without laundry stress. The Eddie Bauer Citrus Shirt Jacket is packed with down insulation and treated with a durable water-repellent shell to beat the elements. While we’re talking about the brand, Eddie Bauer’s Athletic Fit Rainer Pant is also durable, stretchy, and versatile enough for both the trail and casual Fridays at the office. It’s the kind of performance-minded pant that actually looks good, and works in multiple settings.

Lacoste polos are timeless, polished, and breathable—instantly elevating jeans or shorts without trying too hard. Since they rarely go out of style, scooping one up at a discount is a no-brainer. Bamboo Cool undershirts are a serious upgrade from basic cotton because they’re softer, breathable, and wick sweat to keep you comfortable all day. Replacing old undershirts with these makes every outfit feel better, especially when they’re on sale.

We can’t emphasize enough how crucial it is to grab these deals right away. I’ve seen items sell out in record time over the last few years, so this is no time to mess around.

SHOP PRIME DAY MENSWEAR DEALS

Other Deals We Love

Best Prime Big Deal Days Sales | Prime Big Deal Days Tech Deals | Prime Big Deal Days Hiking Gear Deals | Prime Big Deal Days Braun Deals | Prime Big Deal Days Fitness Editor Picks | Prime Big Deal Days Watch Deals | Prime Big Deal Days Cole Haan Deals | Prime Big Deal Days Golf Deals | Prime Big Deal Days Garmin Deals | Prime Big Deal days Brooks Deals | Prime Big Deal Days Bulk Toiletries Deals

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As the Style and Commerce Editor for Men’s Health, Joseph covers all-things fashion and grooming. Previously, Cheatham was a commerce editor for Spy, and he has written for Travel + Leisure.

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