The Best Prime Day Men’s Fashion Deals From Levi’s, Calvin Klein, Nike, Champion & More

Amazon prime day fashion deals
Courtesy of Amazon

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Amazon Prime Day 2021 is officially here — and we’re so excited! The savings are running through today and tomorrow, June 21st and June 22nd, and there are plenty of Prime Day deals worth checking out.

As Spy editors, we’re always on the lookout for the best Amazon deals, so naturally Prime Day is our time to shine. We’ve got a huge round-up of the best Amazon Prime Day deals that we’re keeping updated, as well as specified pieces like Prime Day tech deals, Prime Day TV deals and, obviously, fashion deals. You can only access all of the savings if you’ve got a Prime account with Amazon, so be sure you’re signed up before the big day.

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Now, 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 the brand’s website or on 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 for Prime Day.  If there’s a birthday or big event 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 definitely watch throughout the sales event.

You can view all the Prime Day menswear clothing sales that are happening right now on Amazon. To help you save time and not get lost in the wonderland that is Amazon, we’ve put together the best of the best deals on men’s clothing, shoes and accessories that you can scoop up right now.


Save Up to 55% Off Levi’s Men’s Jeans

$59.50 $26.89

Levi’s denim is still some of the best in the biz, and a bunch of their top styles are majorly discounted for Prime Day. We’ve picked out two of our favorite pairs that are available at majorly reduced prices, but you should definitely check out their entire brand page on Amazon throughout the sales events to see what they have to offer.

55% OFF

Levi's jeans, best Amazon prime day fashion deals Courtesy of Amazon


levi's men's jeans, best Amazon prime day fashion deals Courtesy of Amazon

Shop Levi's Prime Day Deals


Save Up to 28% On Calvin Klein Jeans

$69.50 $49.99

Jeans are a fashion staple, and Calvin Klein makes great pairs that are now discounted for Prime Day, sometimes as much as 28%. Black skinny jeans are as versatile as dark wash. They’ll look equally cool worn with Chucks or loafers. They hit right below the waist and are made of a cotton stretch blend for comfort.

28% OFF

calvin klein jeans, best Amazon prime day fashion deals Courtesy of Amazon

16% OFF

Calvin Klein men's jeans, best Amazon prime day fashion deals Courtesy of Amazon

Shop Calvin Klein Prime Day Deals


Save Up to 40% Off Tommy Hilfiger Apparel

$49.98 $29.99

Tommy Hilfiger’s stylish, sophisticated apparel has been a staple for years and today they’re offering some signature pieces at major discounts. Polos, shorts, button-ups and hats are all discounted today through tomorrow as well as some of their pajama options. Stock up for the next few seasons and save big time through Tommy’s fashion deals for Prime Day.

40% OFF

Tommy Hilfiger men's chino shorts, amazon prime day fashion deals Courtesy of Amazon


Product Spotlight: 38% Off Champion Backpack

$40.00 $24.75 

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. Their manuscript backpack is currently on sale for 38% off and is available for only $24.75. It’s got a standard design of a larger main compartment and four internal pockets for organization, and the straps are padded for comfortable carrying. The embroidered logo adds a nice touch, and it’s available in a whole slew of colors.

38% OFF

champion backpack, best Amazon prime day fashion deals Courtesy of Amazon


Save 36% on Champion Men’s USA Reserve Weave Sweatshirt

$75.00 $48.00

The Olympics are coming up! And this sweatshirt from Champion is the perfect way to support team U.S.A during the summer games this year. It’s got 15-inch vintage script and USA motifs all over, and the bright red color will set you apart. Plus, today during Prime Day you get 36% off this exclusive sporty look just in time for the games to start.

36% OFF

champion USA sweatshirt, best Amazon prime day deals Courtesy of Amazon


Get Up to 40% Off Nautica Men’s Apparel

$24.99 $19.66

It’s summer, and it’s the perfect time to rock some sporty, sophisticated apparel from the menswear brand Nautica. They make stylish polos, shorts and other casual men’s clothes that look perfect next to a boat or by the sea. This polo is 21% off, but they’ve got a bunch of other discounts on their stylish button-ups, pants, pullovers and even pajamas.

21% OFF

nautica men's polo shirt, best Amazon prime day deals Courtesy of Amazon


Get Up to 25% Off Bates Tactical Boots

$119.95 $90.47

Bates tactical boots are comfortable and incredibly 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 all the way to your ankle from the arch.

25% OFF

Bates tactical boots, best Amazon Prime Day fashion deals Courtesy of Amazon


Carhartt Loose Fit Midweight Graphic Sweatshirt

$39.99 $31.99

Carhartt fashion deals are always worth noting, especially when this stylish crew neck sweatshirt is 20% off for Prime Day and available in three different colors. It’s got a front neck V-patch and stretchable rib-knit cuffs and a waistband for a comfortable and form-fitting look.

20% OFF

carhartt rib knit crewneck sweatshirt, best Amazon prime day fashion deals Courtesy of Amazon


Save Up to 63% On Invicta Divers Watches

$78.82 $55.17

Invicta makes super stylish and functional divers watches that tow the balance between utility and design, and they’re available at steep discounts over Prime Day. This model has a stainless steel case and a black watch face that magnifies the look of the numbers. The stainless steel band is adjustable by adding or removing links and it’s 200 meter water resistant.

30% OFF

Invicta divers watch, best Amazon prime day fashion deals Courtesy of Amazon


Save Up to 20% Off Accessories from Timberland


Everyone needs a solid classic leather belt, and this one from Timberland is perfect and only $20 over Prime Day. It’s made with 100% genuine leather and has a classic antique finish buckle out front. It can be worn just as easily with jeans as it can with a dress, and it comes in five different colors for all outfits.

Timberland men's leather belt, best Amazon prime day fashion deals Courtesy of Amazon

Timberland Prime Day Accessory Deals


UGG Pismo Sneakers For Under $100

$119.95 $93.91 

The perfect WFM sneaker that also looks good at brunch. UGG has quickly developed a reputation for making fashionable footwear that’s also comfortable. Take advantage of the Prime Day sale and grab these chestnut suede slip-ons, your feet will thank you.

22% OFF

prime day menswear deals - UGG Pismo Slip-On Sneaker Courtesy of Amazon


Save Up to 38% on Under Armour Gear

$25.00 $16.52

Under Armour, the fitness gear giant, is offering up to 38% off their signature sweatshirts, shirts, shorts, compression leggings, gym bags and more for Prime Day. This brand knows their 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.

34% OFF

under armour tech shirt, best Amazon prime day fashion deals Courtesy of Amazon


Save 50% on Fossil’s Nate Stainless Steel Quartz Watch

$165.00 $82.50

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. This deal from Fossil is live now, and offers one of their sleekest, highest rated watches for more than $80 off. If you need a great birthday gift for your boyfriend or a gift for dad for a belated Father’s Day, it’s a great option.

50% OFF

fossil stainless steel watch, Amazon prime day deals Courtesy of Amazon


Product Spotlight: Fossil Men’s Leather Bifold Wallet

$48.00 $39.95

Fossil is a great brand for wallets, watches and other men’s accessories, and one of their most popular wallets on Amazon is on sale for Prime Day. It’s made of 100% cowhide leather and has a slim design that’ll fit perfectly in your back pocket. It’s got plenty of compartments for cash and cards, an ID window and comes in five different colors.

17% OFF

fossil wallet, Amazon prime day fashion deals Courtesy of Amazon


Up to 50% off Calvin Klein Underwear for Men & Women

$42.50 $21.13

Because everything 90s is new again, Calvin Klein underwear is still extremely popular in 2021. Both men and women are rocking the designer’s signature underwear, which is discounted 50% for Prime Day 2021. While new underwear isn’t quite as exciting as a new 65-inch TV, you should definitely take advantage of this deal and stock up on undies.

50% OFF

top prime day deals Courtesy of Amazon


Save Up to 36% Off SAMSUNG Galaxy Smart Watch

$249.99 $149.99 

Smartwatches are the wave of the future — putting smartphone capabilities on our wrists. For Prime Day there are already sizable discounts on some big ticket smart fashion items from brands like Samsung, including this watch that’s available for 40% off its original price. Don’t hesitate — this deal won’t last forever!

40% OFF

samsung galaxy watch, best Amazon prime day fashion deals Courtesy of Amazon


Samsonite Tectonic Lifestyle Sweetwater Business Backpack

$114.99 $91.05

We’re slowly going back to commuting to work, and if it was ever a time to upgrade your backpack, doing so during the Amazon Day Prime Day sales 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 if you’re not using any of the multiple interior folders, they can be compressed to give you more room.

21% OFF

samsonite techonic back backpack Courtesy of Amazon


Save Up to 28% Off Timex Watches

$45.00 $32.90

There are watches, and then there are Timex watches. They have a reputation built on timepieces that can survive anything and almost everything, still work and still look good. Toying with the idea of getting 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.

27% OFF

Timex expedition acadia mens watch Courtesy of Amazon


Timex Weekender 38mm Watch

$57.00 $41.30

You can’t go wrong with a Timex watch, and this one is currently 28% off for Prime Day 2021. These affordable timepieces have a classic and timeless appeal that never goes out of style, and right now Timex has huge deals on some of their most popular men’s and women’s watches. We especially love the brand’s Weekender Watch, currently 28% off for Amazon Prime members.

28% OFF

top prime day deals of 2020 - timex watches Courtesy of Amazon


14. Wrangler Men’s Retro Snap Button Shirt 

$56.00 $34.99

American heritage brand Wrangler has long been a cowboy’s best friend. Over the years, they’ve spread their fashion wings to include city slickers. Many of their items are reduced now, and will continue through the sale. Westernwear has gone from an occasional hot trend into part of mainstream men’s fashion, and adding a classic snap-button shirt or bootcut jeans adds versatility to your wardrobe.

38% OFF

Wrangler Men’s Retro Snap Button Shirt Courtesy of Amazon


Save Up to 37% Off Nike Men’s Running Shoes

$140.00 $84.99

Whether this is the year that you’ve decided to take up running, or you’re an avid marathoner, chances are Nike’s running shoes are on your radar. Even if you’re not a runner, you can’t pass up a deal on the brand. These Rn running shoes from them are discounted 39% on Amazon for Prime Day, and there are most likely going to be more deals as the sales event rolls on.

39% OFF

nike men's running shoes, best Amazon prime day fashion deals Courtesy of Amazon


Save 50% Off MeetSun Unisex Polarized Sunglasses

$25.99 $12.96 

Sunglasses are part and parcel of a summer wardrobe. They’ll protect your eyes against harmful UVA and UVB rays, ease eyestrain when driving, and generally look cool. While there are 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 thousand positive reviews, these inexpensive unisex sunglasses are on everyone’s must-have list. Normally, the sunnies price hovers around $25, for early Prime, the price has plunged 50% and they’re such a good deal, you could pick up two of them.

50% OFF

Meet Sun Unisex Polarized Sunglasses Courtesy of Amazon


Save Up to 29% Off adidas Men’s Gear

$85.00 $60.65

Adidas is another activewear giant that can neatly mix performance gear with streetwear style. Whether it’s footwear, clothing, accessories, or gear, the consistently create items that combine cutting edge technology with style. Many of their outerwear items and gym bags are on sale for Prime Day, including this sleek rain jacket and warm-up sweatshirt.

29% OFF

adidas golf rain jacket, best Amazon prime day deals Courtesy of Amazon

adidas warm-up sweatshirt, best Amazon prime day deals Courtesy of Amazon


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