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Prime Day Is Back! Re-Up on Men’s Fashion Essentials With 40% Off From Calvin Klein, Levi’s & Timex

That’s right. It’s almost here. Prime Day 2022 takes place on October 11 and 12. That said, it’s time to grab your wallet and get ready for the shopping event of the year.

We’ve rounded up some of the best Prime Day fashion deals for 2022. In this post, we’ll share the latest Prime Day deals on menswear, footwear and accessories. Keep checking back, because in addition to the early deals listed below, we’ll be regularly updating this post as new Prime Day deals on apparel go live.

This comes in addition to our huge guide to the best Amazon Prime Day deals, which you’ll also want to keep a close eye on as the big day draws near.

If you’re not already an Amazon Prime member, you’re going to want to sign up ASAP so you can take full advantage of the best Prime Day deals. With the membership, you’ll immediately gain access to all the benefits that Prime Day has to offer.

Amazon Prime 30-Day Free Trial!

You may not think of Amazon as your go-to fashion outlet, and we know that SPY readers do a lot of their online clothes shopping either directly on a brand’s website or from fashion retailers like Nordstrom and Mr Porter. However, Amazon is beefing up its selection of clothing and accessories from big brands like Levi’s, Calvin Klein, Tommy Hilfiger and more. To lure in shoppers, the company has some pretty stellar fashion deals going on now for both men and women ahead of Prime Day. If a birthday or big event is coming up, Prime Day deals will give you a leg up in the gift department. We’ve gathered some of our favorite fashion deals below from brands you should watch throughout the sales event.

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You can view all the Prime Day menswear clothing sales happening right now on Amazon. To help you save time, we’ve put together the best of the best deals on men’s clothing, shoes and accessories that you can scoop up right now.

  

Prime Day 2022 Deal: Adidas

Adidas is one of the most popular activewear brands and we’re seeing some amazing Prime Day deals for their essential items including the universally-adored tracksuit top and ultraboost running shoes. You can enjoy as much as 50% off on select apparel.

Adidas Men’s 3-Stripe Track Top

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Adidas Men’s Essentials Fleece Tapered Cuff 3-Stripes Pants

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Adidas Men’s Marathon Jacket 3-Stripes

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Adidas Men’s Ultraboost C.rdy Running Shoe

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Amazon Prime Day 2022 Deal: Levi’s 

Levi’s denim is still some of the best in the biz. Recently, Levi’s made waves for revamping their 70’s-era collection of men’s boots. And now, their brand is having some really cool deals on everything hoodies and trucker jackets to their popular denim trousers. We’ve picked out one of our favorite pairs that are available at majorly reduced prices, but you should check out their entire brand page on Amazon throughout the sales events to see what they have to offer.

Men’s Fillmore Rugby Hoodie

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Levi’s Men’s Sherpa Trucker Jacket

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Levi’s Men’s 505 Fit Jeans

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Prime Day 2022 Deal: Amazon Essentials

Prime Day, the Sequel is bringing you plenty of good knits including turtlenecks, v-neck and crewneck sweaters as well as shawl cardigans from Amazon Essentials. All of the above will keep you cozy during sweater weather. Enjoy up to 30% off on these fall-winter necessities.

Men’s Long-Sleeve Soft Touch Cardigan Sweater

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Amazon Essentials Men’s Long-Sleeve Soft Touch V-Neck Sweater

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Prime Day 2022 Deal: Calvin Klein Underwear

Recently, we rated Calvin Klein the best OG underwear brand in the game after testing hundreds of different pairs. Over the years, Calvins have become the modern underwear to make guys look and feel better. Lucky for you, you can snag a few pairs for 30% off right now.

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Prime Day 2022 Deal: SAXX Men’s Underwear

SAXX Underwear is one of our SPY team’s personal favorites. Designed for freedom of movement, these boxer briefs have all the breathability and comfort you need to unwind. The only issue we’ve ran into with the brand was the price. But today, that won’t be a problem you have to worry about. You can enjoy 30% off.

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Prime Day Ray-Ban Deals

This year, some of the best Prime Day fashion deals are on Ray-Ban designer sunglasses. In fact, there were so many great deals in this category that we devoted an entire post to the Top Prime Day Deals on Ray-Ban Sunglasses. We found Ray-Ban aviators for under $100, as well as 25% discounts on Clubmaster sunglasses and Ray-Ban Stories smart glasses.

Keep scrolling to see some of the top deals from Ray-Ban.

Ray-Ban Clubmaster Sunglasses

ALMOST SOLD OUT
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Ray-Ban Rb3447 Round Metal Sunglasses

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Ray-Ban Rb4298 Aviator Sunglasses

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Ray-Ban Stories Smart Glasses

SAVE 25% NOW
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Prime Day Deals on Crocs

You simply can’t knock savings on Crocs. The world’s favorite little shoe that could is currently on our radar as one of the best fashion deals going on for Prime Day. And we’re talking multiple styles, including the tie-dye lined clogs, Bayaband Slide Sandals, fuzzy slippers and flip flops.

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Prime Day Fashion Deals: Hanes Essentials

Hanes essentials are currently on sale just before Prime Day at up to 44% off. Here’s the deal, though: Hanes products are already affordable. Now, they’re even more. That said, you’re practically getting these Hanes products for free. This is one you’re not going to want to miss out on.

Hanes Ultimate Ultimate Tagless Slim Fit Crew Undershirt

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Hanes Men’s Jogger Sweatpants

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Hanes Men’s Max Cushion Crew Socks

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Prime Deals on Champion Gear

Champion is another brand to look out for ahead of Prime Day as they’ve got stylish streetwear that’s typically discounted heavily during the sales event. Over the past few months, we’ve seen many of these items get high deductions so we’re expecting to see prices drop even lower during this annual savings event. Check out a few of our favorite pieces from Champion below.

Champion Backpack

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Champion Pullover, Powerblend Fleece Midweight Hooded Sweatshirt

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Champion White Logo T-Shirts

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Champion Dad Hat

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Champion Men’s Lightweight Jersey Joggers

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KEEN Hiking Boots

Ready for a hike? There’s nothing that will keep your feet more comfortable and provide support than a hiking boot. With immense traction and total breathability, KEEN makes a stellar boot design perfect for taking on the trails.

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Apple Watch Series 7

Apple Watches are considered fashion, right? Right. The Apple Watch Series 7 is currently on sale for a whopping 28% off, which is a $120 markdown in total. This most recent Apple Watch release is the best we’ve seen so far with out-of-this-world health innovations, a customizable design, immense durability and, of course, an ever-so-sleek look.

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Nautica Men’s Apparel

Now that summer gone, it’s the perfect time to rock up some sophisticated fall apparel from menswear brand Nautica. They make stylish polos, soft knitwear and other casual men’s clothes that look perfect next to a boat or by the sea. This blue coral quarter-zip sweater is just an example of what we expect to see from this year’s event but we’re predicting that they’ll offer other big discounts on their stylish button-ups, pants, pullovers and even pajamas.

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Prime Day Tommy Hilfiger Deals

Right now, you can also save huge on must-haves from Tommy Hilfiger. These preppy items have summer written all over them. From backpacks to hats to sweater vests (yes, sweater vests really are back in style) and more, you can pick up tons of Tommy styles on Amazon right now with some serious price drops.

Tommy Hilfiger Men’s Cotton Sweater Vest

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Tommy Hilfiger Men’s Long Sleeve Fleece Logo Pullover Hoodie Sweatshirt

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Fruit of the Loom

Prime Day isn’t just a chance to score great deals on OLED TVs and other expensive items. Savvy shoppers who really want to make the most of Prime Day should also look at stocking up on the everday, low-cost items that are also on sale. And some of the best Prime Day fashion deals of 2022 definitely fall into the basics category, like the below deals on Fruit of the Loom underwear.

Fruit of the Loom is essential when it comes to men’s underwear. There’s no way you haven’t worn something from Fruit of the Loom in the past, whether it be their affordable undershirts or classic tagless boxer shorts, so we’re sure this is a sense of comfort you’re already familiar with. Right now, you can snag Fruit of the Loom products at 30% off right now, including these tagless boxer briefs below. Time to replenish!

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Prime Day 2022 Deal:  Bates Tactical Boots

Bates tactical boots are comfortable and durable for the outdoors. These boots have a grippy, slip-resistant rubber outsole as well as a performance leather upper. They have a YKK side zipper for easy on/off and the shaft measures to your ankle from the arch.

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Prime Day 2022 Deal: Dockers

Need to upgrade your work wardrobe? Then don’t miss these Prime Day fashion deals on Dockers pants and apparel.

Dockers Slim Fit Lux Cotton Stretch Pants

In the need of some new clothing for the office? Then Prime Day is the time to help you save up to 65% on Dockers. From long-sleeve button-downs to khaki pants, Dockers has everything you need to keep a cool, calm and collected look in the office this season.

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Dockers Long Sleeve Flex Shirt

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Marmot Outerwear

Although jacket season is far, far away, there’s never been a better time to save on Marmot outdoor gear than right now. This winter jacket is everything you need for cold weather in the coming seasons and right now, you can save $100 on it.

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Under Armour Gear

Under Armour, the fitness gear giant, will likely be offering savings on their signature sweatshirts, shirts, shorts, compression leggings, gym bags and more for Prime Day. This brand knows its stuff when it comes to high-performance gear that’ll keep up with you and your hustle, and now you can get pieces for you and the whole family through a great deal.

Under Armour T-Shirts

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Under Armour Cold-Weather Gear

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Seiko Watches & Accessories 

Watch deals are pretty much always cycling in and out on Amazon, and Prime Day always spurs an onslaught of them in the men’s style space. If you need a great birthday gift for your boyfriend or a gift for dad for a belated Father’s Day, Seiko watches are a great option.

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Prime Day Fashion Deals: Backpacks

The top Prime Day fashion deals of 2022 include outdoor apparel, athleisure, footwear, and work clothing, but this year’s sales also include some great sales on backpacks. So far, we’ve found big savings on popular backpacks from UGrace, Samsonite, and Adidas.

UGRACE Vintage Laptop Backpack

UGRACE makes me it easier to be on the go. Especially when your phone’s battery needs more juice. Yes, this innovative backpack produced with premium lightweight tear resistant oxford fabric, has a USB charging port. And, it’s very spacious with 6 compartments to store your laptop and other personal belongings. The shoulder bag is currently discounted 43% off it’s original price.

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Samsonite Tectonic Lifestyle Backpack

We’re back to commuting to work, and if there was a time to upgrade your backpack, Amazon Day Prime Day is a no-brainer. Samsonite’s backpack can fit up a 17-inch laptop and keep it safely cushioned in its own pocket. It has a USB port for charging anything and it’s constructed so that you can compress any of the multiple interior folders when not in use.

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Lacoste

One of America’s favorite preppy brands is also having a sale during Amazon Prime Day. Save big on Lacoste now. You know, the brand that uses a little alligator as their on-shirt mascot. This short-sleeve button-down is one of our personal favorites that you can pick up for 45% off right now.

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Columbia

Hiking boots? Check. Fleece pullovers? Check. Tees? Checkity, check, check. This year for Prime Day, everyone’s favorite outdoor clothing brand is giving us deals on deals on deals. Pick up wild savings from Columbia below.

A lot of the top Prime Day fashion deals of 2022 include outdoor apparel from brands like Columbia and prAna. If you’re looking for more great deals in this vein, check out our guide to the best Prime Day deals on athleisure clothing.

Columbia Men’s Newton Ridge Plus II Suede Waterproof Boot

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Columbia Men’s Steens Mountain 2.0 Full Zip Fleece Jacket

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Calvin Klein Underwear for Men & Women

Because everything ’90s is new again. Both men and women are rocking the designer’s signature underwear, which you’ll be able to snag at a discount for Prime Day 2022. While new underwear isn’t quite as exciting as a new 65-inch TV, you should take advantage of this deal and stock up.

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Timex Watches

There are watches and then there are Timex watches. They have a reputation for timepieces that can survive almost everything, still work and still look good. Toying with the idea of a casual watch? Go ahead and use the excuse of the Amazon Prime Day sale to buy the rugged-looking Timex Expedition Acadia watch. It has a 39 mm case, a light-up watch dial and luminous hands.

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Timex Weekender 38mm Watch

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Sperry STRIPER II CVO Core Sneaker

Right now, you can save 20% on the Sperry STRIPER II CVO Core Sneaker. But, that’s not the only savings you should anticipate with this one. Before you click “Add to Cart”, make sure you check off the little box in the description that allows buyers to save an additional $11.24, bringing the price all the way down to just $36.72

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Gildan

We love Gildan for the sheer fact that it’s beyond cheap. Like, the cheapest underwear you can purchase on the whole planet kind of cheap. Now, to make things even more affordable, Gildan is on sale even further for Prime Day. Pick up some undies, tees and more.

Gildan Men’s Heavy Cotton T-Shirt 10-Pack

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Gildan Men’s Cotton Stretch Boxer Briefs 4-Pack

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Prime Day Fashion Deals: Wrangler Jeans

Wrangler is a jean brand that’s right up there with Levi’s. Right now, you can get a number of Wrangler jeans on sale that are sure to last you many years to come. They’re durable, reliable and comfortable day in and day out, so you aren’t going to want to miss out on these deals while they’re going on.

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One More Thing…

Finally, if you still haven’t found what you’re looking for in the Prime Day deals on men’s clothing and accessories above, then we have two more items for you to consider.

MeetSun Unisex Polarized Sunglasses

While there is a range of sunglasses doing the early Prime Day Sale right now, there are two brands that we wanted to highlight. We’ve written about Meet Sun before. With over 5,000 positive reviews, these inexpensive unisex sunglasses are on everyone’s must-have list.

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Adidas Long-Sleeve Tee

Adidas is another activewear giant that combines performance gear with streetwear style. Whether it’s footwear, clothing, accessories or gear, they consistently create items that combine cutting-edge technology with style. Many of their outerwear items and gym bags will be on sale for Prime Day, including this warm-up sweatshirt.

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The Best Amazon Prime Day Deals on Laptops