Prime Big Deal Days Men’s Clothing Sales

UNLIKE BLACK Friday and Cyber Monday, Amazon Prime Day fashion deals come twice a year now! This time around in the form of Prime Big Deal Days, starting at 3 a.m. EDT on October 10, and running through October 11, according to Amazon’s official press release (it’s right around the corner!). With these October’s Prime Day fashion deals, you can get an early jump on your holiday gifting—well before those other two major shopping events—or just treat yourself to a wardrobe upgrade.

SHOP ALL EARLY PRIME DAY FASHION DEALS

As if that weren’t enough good news, our editors have assembled some of the best early Prime Day fashion deals for you to get a head start on the action, way before Prime Big Deal Days. We combed through the best clothing brands on Amazon to spot discounts on wardrobe essentials like t-shirts, dress pants, jackets, watches, socks, and underwear. It has never been easier or more affordable to stock up for yourself and start knocking off your holiday shopping list nice and early. So check out these killer early Amazon Prime Day fashion deals—some as much as 70% off—before Prime Big Deal Days hits, cause this stuff will sell out quickly!


Best Prime Big Deal Days Clothing Deals

VIEW ALL MEN’S CLOTHING DEALS


Best Prime Big Deal Days Shoe Deals

VIEW ALL FOOTWEAR DEALS

On Sale

Rockland Chelsea Boot

Deer Stags Rockland Chelsea Boot

Now 62% Off

On Sale

997H V1 Sneaker

New Balance 997H V1 Sneaker

Now 28% Off

On Sale

Gel-Kayano 29 Running Shoes

ASICS Gel-Kayano 29 Running Shoes

Now 38% Off

On Sale

OriginalGrand Knit Wingtip

Cole Haan OriginalGrand Knit Wingtip

Now 55% Off

On Sale

Nelson Bay Shearling Indoor/Outdoor Moccasin Slipper

Fireside by Dearfoams Nelson Bay Shearling Indoor/Outdoor Moccasin Slipper

Now 61% Off

On Sale

Sauvie Slip On Waterproof Rain Boot

Bogs Sauvie Slip On Waterproof Rain Boot

Now 55% Off


Best Prime Big Deal Days Watch Deals

VIEW ALL WATCH DEALS

Apple Watch Series 8 [GPS 41mm]

Apple Apple Watch Series 8 [GPS 41mm]

Now 20% Off

Promaster Dive Eco-Drive Watch

Citizen Promaster Dive Eco-Drive Watch

Now 27% Off

On Sale

Marine Star Series C Chronograph Quartz Watch

Bulova Marine Star Series C Chronograph Quartz Watch

Now 43% Off

On Sale

MTGM900DA-8CR Tough Solar Atomic Sport Watch

Casio G-Shock MTGM900DA-8CR Tough Solar Atomic Sport Watch

Now 41% Off

On Sale

"Bambino Version 8" Japanese Automatic Dress Watch

Orient “Bambino Version 8” Japanese Automatic Dress Watch

Now 44% Off

On Sale

T5E901 Ironman Classic

Timex T5E901 Ironman Classic

Now 33% Off

Gentleman Stainless Steel Dress Watch

Tissot Gentleman Stainless Steel Dress Watch

On Sale

Signatur Three-Hand 40mm Minimalist Watch

Skagen Signatur Three-Hand 40mm Minimalist Watch

Now 53% Off


Best Prime Big Deal Days Underwear & Socks Deals

On Sale

Performance Boxer Brief Underwear (3-Pack)

adidas Performance Boxer Brief Underwear (3-Pack)

Now 37% Off

On Sale

Cotton Classics 5-Pack Boxer Brief

Calvin Klein Cotton Classics 5-Pack Boxer Brief

Now 25% Off

On Sale

Classic Cotton Loose Knit Boxer Shorts, 4 Pack

Nautica Classic Cotton Loose Knit Boxer Shorts, 4 Pack

Now 29% Off

656s Cotton Crew Athletic Socks (6-Pairs)

Goldtoe 656s Cotton Crew Athletic Socks (6-Pairs)

Now 32% Off

On Sale

Ankle Sports Socks, 6 Pairs

JOYNÉE Ankle Sports Socks, 6 Pairs

Now 47% Off

Heavyweight Merino Wool Blend Short Crew Sock

Carhartt Heavyweight Merino Wool Blend Short Crew Sock

With Amazon Prime Big Deal Days just around the corner, make sure to stay tuned for updates on these best Prime Day fashion deals because the bargains only get better from here. There is no better time to upgrade your fall wardrobe but you have to stay quick on your browser’s refresh button because these deals come in hot and fast. Like every five minutes fast, during peak hours. Some of our favorite menswear brands like Adidas, Vince, and Cole Haan are included. We’ll keep a cheat sheet of the best prime day fashion deals right here for your convenience.


What Is Amazon Prime Big Deal Days?

Prime Big Deal Days is Amazon’s second Prime Day event of the year, another annual 48-hour deal event exclusively for Amazon Prime Members. According to Amazon, Prime Big Deal Days will take place from October 10 through October 11 as a way to “shop some of Amazon’s best early holiday deals”. Like Prime Day, Prime Big Deal Days includes deals on everything from fashion, electronics, fitness equipment, home, and more.

When Is Amazon Prime Big Deal Days 2023?

According to the official press release, Amazon’s second annual two-day savings and shopping event starts on October 10 at 3 a.m. EST and runs through October 11.

What Will Amazon Prime Big Deal Days Fashion Deals Include?

Prime members this year can enjoy significant savings on renowned men’s clothing brands on Amazon such as Goodthreads, Bruno Marc, Hanes, Legendary Whitetails, and more. They can also take advantage of exclusive discounts on new Amazon-exclusive deals from brands such as Alo Yoga. In addition, Prime members will have access to the lowest prices offered by Amazon so far this year on selected products from a diverse range of menswear brands including Hey Dude and Amazon Essentials.

Who Can Participate in Amazon Prime Big Deal Days?

Prime Big Deal Days sales are exclusive to Prime members. You can sign up here if you’re ready to make that commitment. A Prime subscription is $14.99 a month, or $139 per year. While that end-of-year number may sound like a lot, you do get a bang for your buck. On top of exclusive access to Prime Day deals (including loads of Prime Day fitness deals), you also get two to same-day shipping on select items. (Also: Amazon is offering 30-day trials for new customers, just in case you’re not ready to pay full price, so you can time your sign-up to the dates of Prime Day this year.)

Shop More of the Best Prime Day 2.0 Deals, Below

Prime Day Tech Deals | Prime Day Sneaker Deals | Prime Day Watch Sales | Prime Day Hoka Deals

Bookmark this page as we’ll be updating the best Amazon Prime Day fashion deals here as the event continues, with the best deals on men’s clothes, footwear, accessories, and more.

Headshot of Brad Lanphear

Contributing Commerce Style Writer

Brad is a contributing style commerce editor. After a decade working for menswear brands including J.Crew and Ralph Lauren, Brad switched from selling fashion to writing about it. His words have appeared in Huckberry, Heddels, and The Manual.  

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