32 Amazing Prime Day Fashion Deals on Levi’s, Nautica, Calvin Klein & More (Updated)

amazon prime day fashion deals 2020
Product Photos Courtesy of Amazon
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Amazon Prime Day 2020 is finally here! After months of delays and rumors, Amazon Prime Day began yesterday and is taking place right now until the end of the day. This means shoppers will have the rest of today to take advantage of the more than 1 million deals, so you better hurry on up and get shopping!

Even better, this year’s sale is set to feature some of the best Amazon Prime Day’s fashion deals we’ve ever seen — so let’s dive in.

Originally scheduled for early July, Prime Day got pushed back due to COVID-19 (like lots of other things). If you’ve never taken advantage of Amazon Prime Day deals before but you love a good bargain, this annual sale should definitely get your attention. And this year, Amazon is going all-in on fashion deals with crazy bargains from brands you love like Adidas, Champion, Timberland, Levi’s, Lee Jeans, Cole Haan and more. If you occasionally shop Amazon but aren’t a Prime member, you can sign up for a free 30-day Amazon Prime membership and cancel before the free month expires.

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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, and to lure in shoppers, the company released Amazon Prime Day fashion deals two weeks early.

Call it the Pre-Prime Day sale, or a preview sale, or whatever you want — the early fashion deals are amazing.

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 eight amazing deals on men’s clothing, shoes and accessories that you can scoop up right now.


1. Lacoste Apparel


Let’s get it, baby. From the makers of our favorite polos, sneaks and underwear comes one of the hottest deals of the day: Lacoste’s sale that’s reaching almost completely half off their original pricing. Typically, a regular Lacoste polo could reach higher than $100, but right now, we’re seeing prices drop to under $50. You can even snag a handsome messenger bag for commuting at a whole 30% off traditional retail price from Lacoste. You better hop on it, though, these deals are only available for the rest of the day!

Lacoste Men's Short Sleeve L.12.12 Pique Polo Shirt Courtesy of Amazon

Save Up to 45% on Lacoste During Amazon Prime Day


2. Levi’s Jeans

SAVE 40% 

Levi’s is an iconic brand and their jeans are a wardrobe staple. You’ve probably had a pair in your closet when you were a kid, and as you grew, you always had at least one pair of their jeans. Depending upon the style Levi’s prices hover between $60 to $120, so when they’ve got hefty discounts on their jeans, jackets and high-quality denim you don’t hesitate, you go for it. They’ve got choices for men and women, so don’t hesitate to pick up some staples for yourself and grab a few early gifts while sizes are still in stock.

Levi's Jeans, top amazon prime day fashion deals 2020 Courtesy of Amazon

Save Up to 40% on Levi's During Amazon Prime Day


3. Nautica Apparel


It’s time to treat yourself. If you wouldn’t necessarily buy Nautica clothing apparel, right now’s finally the time. Nautica is currently operating on Prime Day with up to 30% of a slew of incredible picks with tons of sizing options. We’re currently obsessing over this robe, because why not? You deserve it.

Nautica Men's Long Sleeve Lightweight Cotton Woven Robe Courtesy of Amazon

Save Up to 30% on Nautica Apparel During Amazon Prime Day


4. Columbia Apparel and Shoes


Columbia, the Patagonia-esque outdoor gear company is offering steep discounts on their top-of-the-line gear this Prime Day. You’ve still got a chance to take advantage of their offers and pick up some gear for winter and future outdoor adventures. They’ve got deals on fleeces, jackets, hiking boots and more. This men’s fleece has over 7,000 5-star reviews on Amazon and is currently 50% off. It’s thick, warm and very layer-friendly for the cold months ahead.

Columbia men's fleece, prime day fashion deals Courtesy of Amazon

Save Up to 45% on Columbia Apparel and Shoes During Amazon Prime Day


5. Adidas Apparel, Footwear & Accessories


If you’ve been a fan of Adidas gear, but hesitated to buy their things because of the price tag, it’s the  Amazon Prime Day Sale to the rescue. They have tons of different clothing, footwear and accessory options to choose from that are on sale right now, like this cotton fleece hoodie. After a long day, pop this on and it’s instant comfort. The hoodie has kangaroo pockets and sports the brand’s iconic three stripes down a sleeve.

adidas black lock up hoodie Courtesy of Amazon

Save Up to 40% on adidas Apparel, Accessories & Footwear During Amazon Prime Day


6. Timberland Accessories


It doesn’t get more premium than Timberland’s line of wallets and belts. If you’ve ever had the chance to throw on a pair of an ever-so-classic Timberland boot, you’ll know that these products are made with incredible quality and care. Though you can’t get a pair of boots for any cheaper than normal right now, you can currently save big on a ton of the brand’s much-desired accessories. And we know dang well you’re going to need a new belt after months of quarantine, so, get shopping, bud.

Timberland Men's Classic Leather Jean Belt Courtesy of Amazon

Save Up to 40% on Timberland Accessories During Amazon Prime Day


7. Lucky Brand Men’s 181 Relaxed Straight Jean


When you see premium jeans that are 40% off, don’t hesitate, grab them. This year, a lot of the top Prime Day deals on men’s apparel include designer jeans, so it’s the perfect time to update your fall wardrobe. Lucky Brand jeans are high-quality and comfortable, and right now a whole bunch of their jeans are steeply discounted.

lucky brand jeans Courtesy of Amazon

Save Up to 40% on Lucky Brand Jeans


8. New Balance Footwear


Say what you will about how they look, New Balance sneakers are comfortable AF and there’s a reason they’ve been around for so long. The quality is unparalleled, and the chunky shoes have recently come back into style as a nostalgia play, so there’s really no reason to not buy them. Prime Day has also lowered their prices to deals that are hard to ignore, with as much as a 40% discount on some pairs. They’ve got choices for men, women and children as well so no one in the family is left out. Don’t miss out!

New Balance sneakers, Amazon Prime Day, men's fashion deals, prime day deals Courtesy of Amazon

Save Up to 35% on New Balance for the Whole Family


9.  Herschel Novel Duffel Bag

Was $89.99, Now $59.64 | SAVE $30.35

Use the padded shoulder strap or carry it by hand, either way this snazzy Herschel duffle bag amps up your weekend away or gym game. It has an outer zippered compartment and at 42.5L, it will carry more than you need.

herschel blue novel duffel bag Courtesy of Amazon

10. Calvin Klein Men’s Skinny Fit Jeans

Was $79.50, Now $29.19 | SAVE $53.01

This is the joy and the craziness of Amazon Prime Day sales; you find luxe items like these Calvin Klein jeans for over 50% off. 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.

Black Calvin Klein Men's Skinny Fit Jeans top prime day deals of 2020 Courtesy of Amazon

11. Tommy Hilfiger Apparel


Tommy Hilfiger’s stylish, sophisticated apparel has been a staple for years and today they’re offering some signature pieces at major discounts. Polos, handbags, 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 Prime Day deals.

Tommy Hilfiger cotton v-neck sweater, Amazon prime day deals Courtesy of Amazon

Save Up to 70% on Tommy Hilfiger Apparel During Amazon Prime Day


12. Save Up to 60% on Watches from Citizen


Anyone that needs a new timepiece would be foolish to pass up this opportunity to score great deals on stylish watches from some of our favorite brands. For women, you can find great deals on watches from Kate Spade, Anne Klein and GUESS, while guys can buy a new watch from TIMEX or Citizen. There are hundreds of watches on sale, and this is one of the top Prime Day fashion deals of 2020.

prime day fashion deals Courtesy of Amazon

See All Prime Day Deals on Watches


13. UGG Pismo Slip-On Sneaker

Was $119.95, Now $67.99 | SAVE $51.96

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 pre-Prime Day sale and grab these chestnut suede slip-ons, your feet will thank you. As a gift or for your own feet, you can’t go wrong with Ugg slip-ons, which is why these are one of the top Amazon Prime Day fashion sales of 2020.

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

14. Under Armour Apparel and Shoes


Under Armour, the fitness gear giant, is offering up to 50% off their signature sweatshirts, shirts, shorts, compression leggings, gym bags and more. 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 on Prime Day.

Under Armour t-shirt, Amazon prime day deals Courtesy of Amazon

Save Up to 50% on Under Armour Apparel and Shoes


15. C9 Champion Apparel


This sportswear and athleisure brand is also offering their comfy streetwear/gym attire for great discounts on Amazon Prime Day. You can save on leggings, sweatshirts, sweatpants and workout shirts for fall.

prime day deals on athleisure Courtesy of Amazon

Save Up to 40% on C9 Champion Apparel


16. Calvin Klein Underwear


Want a pair of “my Calvins” — now’s your chance. Their comfortable, soft, cozy and functional underwear is on sale on Prime Day with slashed prices down to $20 for a multi-pack in some cases. They’ve got a variety of styles available at a discount including boxers, boxer briefs, t-shirts and more. Treat yourself to some new, high-quality undergarments at prices your budget can handle.

calvin klein underwear, amazon prime day fashion deal 2020 Courtesy of Amazon

Save Up to 35% on Calvin Klein Underwear


17. Smartwatches from Fossil, Samsung & Fitbit


Smartwatches are the wave of the future — putting smartphone capabilities on our wrists. Prime Day has created major discounts with brands like Fossil, Skagen and Michael Kors offering their high-tech, high-fashion options for big discounts. Jump on these now and achieve the perfect balance of fashion and function.

smartwatches, Amazon prime day deals Courtesy of Amazon

Save Up to 40% on Smartwatches


18. Acorn Ellsworth Slipper

Was $80.00, Now $64.20| SAVE $15.80

Speaking of keeping your feet comfortable, these Acorn Ellsworth blue suede slippers are an Amazon Prime Day Sale steal. Lined in cushy faux fur, they had a memory foam insole that cradles your foot. Best of all, the rubber outsole lets you wear them outdoors and in.

prime day shoe deals for men Courtesy of Amazon


19. Champion Authentic Originals Sueded Fleece Pullover Hoodie

Was $45.00, Now $27.02 | SAVE $17.98

Take advantage of the Amazon Prime Day sale to stock up on cold-weather gear.  This cozy hoodie is perfect for brisk fall mornings and freezing cold winter ones, Champion’s hoodie is lined in soft fleece and is a suede cotton blend on the outside. The brand’s been making activewear since 1919, which means they know how to make clothes for people on the go….and those that like to loll around too.

prime day deals on champion Courtesy of Amazon


20. Watches From Citizen, Bulova, Anne Klein, Invicta and More


One accessory whose price can really rack up? The watch. Prime Day’s a great place to grab one of these top-of-the-line wrist accessories for heavily discounted prices — some as high as 60% off! Don’t miss out, they’ve got a wide variety of styles from sports watches and pilot’s watches to high-end stainless steel and everyday wear.

men's watches, Amazon prime day, prime day deals Courtesy of Amazon

Save Up to 60% on Watches From Citizen, Bulova, Invicta and More


21. Starter Men’s Compression Mockneck Top

Was $19.99, Now $8.90 | SAVE $11.09

Don’t get caught exercising in the cold without a long-sleeve compression tee under your workout clothes. Now’s the time to scoop up deals on winter outer exercise-wear like this compression mock neck top from Starter. This all-white sweat-wicker is perfect for heavy outdoor performance in chilly temps and will keep you warm and cozy your entire workout.

Starter Men's Compression Mockneck Top Courtesy of Amazon


22. Under Armour Charged Toccoa 2 Running Shoe

Was $70.00, Now $52.99 | SAVE $17.01

A lot of people have taken up running. Whether or not you’re a newbie, or you’ve been doing the oval for a long time, you know that Under Armour makes running shoes that are built to last. This lightweight sneaker has an EVA sock liner, two-layer cushioned inner sole, and a mesh combo upper.

under armour prime day 2020- Under Armour Charged Toccoa 2 Running Shoe Courtesy of Amazon


23. Vineyard Vines Clothing for Men


This preppy label makes clothing for lounging and casual dinners out that’s perfect for summer, and great for all seasons. They’ve got t-shirts, pullovers and chambray button-ups like this classic look below that pairs quite well with khakis and loafers. They’ve got shirts, sweatshirts and button-ups all discounted for Prime Day, so get your boat shoes ready.

vineyard vines chambray button-up shirt Courtesy of Amazon

Save Up to 30% on Vineyard Vines Clothing for Men


24. Calvin Klein 3-Pack  Cotton Low-Rise Trunks

Was $42.50, Now $17.90, | SAVE $24.60

While you might want to take advantage of the Amazon Prime Day sale to pick up fun stuff, you always, always need underwear. This is the perfect time to snag a three pack of Calvin Klein’s. These low rise cotton trunks right now cost so much less than they do normally, you might want to pick up two packs.

white calvin klein cotton stretch trunks Courtesy of Amazon


25. Billy Reid Men’s Cashmere Cable Knit Crewneck Sweater with Patches

Was $364.72, Now $181.72 | SAVE $24.60

Now that you’ve got the basics squared away during the Amazon Day Prime sale, go ahead and indulge in something luxe. Billy Reid’s been designing cool, modern menswear that easily fits in your closet. This gray cashmere sweater is trimmed in red and has ski-themed patches.

billy reid cashmere sweater - Billy Reid Men's Cashmere Cable Knit Crewneck Sweater with Patches Courtesy of Amazon


26.  American Apparel Fisherman’s Long-Sleeve Pullover Knit Sweater

Was $58.00, Now $34.80 | SAVE $23.20

If you’re updating your winter wardrobe or hunting down holiday gifts during the Amazon Prime Day sale, you can never go wrong with picking up a fisherman sweater. This one from American Apparel is made from soft, breathable cotton. The slightly loose fit means that it’s easy to layer over anything from a tee shirt to a flannel.

prime day fashion deals -American Apparel Fisherman's Long-Sleeve Pullover Knit Sweater Courtesy of Amazon


27.  Samsonite Tectonic Lifestyle Sweetwater Business Backpack, Black

Was $109.00, Now $58.41 | SAVE $51.58

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.

samsonite techonic back backpack Courtesy of Amazon


28. Eddie Bauer Boundary Pass Parka

Was $160.30, Now $137.40 | SAVE $22.90

Don’t get caught in the cold, literally this winter. If you’ve been on the fence about replacing your winter coat, this Eddie Bauer down parka is an Amazon Prime Day sale fantastic deal. Packed with 650 premium down insulation, you’ll say “What cold?” when wearing it. It has removable faux fur trim on the hood, insulated pockets and ribbed cuffs. The warm parka also comes in navy, gray

Eddie Bauer Down Parka Courtesy of Amazon


29. DELSEY Paris Chatelet Hard+ Hardside Luggage with Spinner Wheels

Was $700.00, Now $213.79 | SAVE $486.21

DELSEY Paris is kinda like the Rolls Royce of luggage. The French company has created hard-sided luggage that can withstand anything the airlines throw at it. They rarely go on sale, and for the Amazon Prime Day sale, the price reduction is, to be honest, insane. This 28-inch spinner will protect anything you pack in it. It’s lightweight (weighs 9 pounds), has three recessed TSA approved locks, and even a braking system.

delsey paris black 28 inch spinner Courtesy of Amazon


30. Adidas Stan Smith Sneaker

Was $75.00, Now $58.08, | SAVE $16.92
Adidas stan smith white and green sneaker Courtesy of Amazon


31. Drake Men’s Merino Wool Socks

Was $17.99, Now $11.06 | SAVE $6.93

Sometimes it’s the little things that make you feel better. Use the Amazon Prime Day sale to indulge in picking up this two-pack of merino wool socks from Drake. The mocha pair is extra cushioned to wear with boots, and the black pair can go with anything else. If you’re stumped for a plush stocking stuffer, this could do the trick.

Drake men's meriono wool socks 2 pack Courtesy of Amazon


32. Timex Expedition Acadia Full Size Watch

Was $45.00, Now $32.90 | SAVE $12.10

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, well 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.

Timex expedition acadia mens watch Courtesy of Amazon