The Best Amazon October Prime Day Deals on Menswear: Shop Levi's, Adidas, Brooks, Columbia and More

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Fall is here. Save on menswear from brands such as Levi's, Columbia, Cole Haan and more.

Fall is officially here, which means now is the time for a wardrobe refresh. We know stocking your closet with enough jackets, jeans, sweaters and shoes to make it through the season can wreak havoc on your wallet, but you don't have to spend a fortune to refresh your wardrobe with Amazon's October Prime Day sale happening now.

Shop October Prime Day Deals

For just two days, October 10 and 11, October Prime Day 2023 — or Amazon's Prime Big Deal Days — offers impressive discounts of up to 70% off on men's clothing and fall wardrobe essentials. Whether you're looking for office-appropriate business casual pieces, sporty sneakers for the gym or cozy sweaters to wear on a date night, we've got your outfits covered.

Best-selling Levi's jeans, Columbia vests, Adidas sneakers and Tommy Hilfiger tees are just a few of the must-have staples you can score at a discount during Amazon's October Prime Day event. Ahead, shop our top picks for the best men's clothing deals to spruce up your fall wardrobe. Plus, check out the best men's sneaker deals during October Prime Day and Amazon's October Prime Day fall fashion sale.

The Best Amazon Deals on Men's Shirts, Jackets and Sweaters

Hanes Men's EcoSmart Fleece Sweatshirt

Hanes Men's EcoSmart Fleece Sweatshirt
Amazon

Hanes Men's EcoSmart Fleece Sweatshirt

Soft, durable fleece will keep you warm in this classic Hanes sweatshirt, available in various colors.

$18 $12

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Wrangler Authentics Men's Long Sleeve Quilted Lined Flannel Shirt Jacket

Wrangler Authentics Men's Long Sleeve Quilted Lined Flannel Shirt Jacket
Amazon

Wrangler Authentics Men's Long Sleeve Quilted Lined Flannel Shirt Jacket

Wrangler's Flannel Shirt Jacket is upgraded with a hood to keep you cozy on cold days. 

$31 $22

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Fruit of the Loom Eversoft Fleece Crewneck Sweatshirt

Fruit of the Loom Eversoft Fleece Crewneck Sweatshirt
Amazon

Fruit of the Loom Eversoft Fleece Crewneck Sweatshirt

Spun cotton makes this sweatshirt extra soft, moisture-wicking and breathable.

$13 $11

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Amazon Essentials Men's Full-Zip Polar Fleece Jacket

Amazon Essentials Men's Full-Zip Polar Fleece Jacket
Amazon

Amazon Essentials Men's Full-Zip Polar Fleece Jacket

With fall officially here, a fleece jacket is a must-have for the cool days.

$30 $24

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PJ Paul Jones Casual Knit Blazer Suit Jacket

PJ Paul Jones Casual Knit Blazer Suit Jacket
Amazon

PJ Paul Jones Casual Knit Blazer Suit Jacket

You can never go wrong with adding a simple blazer suit jacket to your wardrobe. Plus, you can pair it with a t-shirt or sweater. 

$80 $56

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Tommy Hilfiger Men's Ultra Loft Lightweight Packable Puffer Jacket

Tommy Hilfiger Men's Ultra Loft Lightweight Packable Puffer Jacket
Amazon

Tommy Hilfiger Men's Ultra Loft Lightweight Packable Puffer Jacket

While lightweight, this Tommy Hilfiger puffer jacket uses faux down to provide extra warmth. 

$70 $59

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Legendary Whitetails Men's Buck Camp Flannel Shirt

Legendary Whitetails Men's Buck Camp Flannel Shirt
Amazon

Legendary Whitetails Men's Buck Camp Flannel Shirt

A 100% cotton flannel is a must for any wardrobe. Flannel is consistently easy to layer and travel with.

$30 $16

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Amazon Essentials Men's Regular-Fit Long-Sleeve

Amazon Essentials Men's Regular-Fit Long-Sleeve
Amazon

Amazon Essentials Men's Regular-Fit Long-Sleeve

This classic long-sleeve shirt is all you need for your work day.

$33 $23

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Columbia Men's Steens Mountain Vest

Columbia Men's Steens Mountain Vest
Amazon

Columbia Men's Steens Mountain Vest

Thanks to this vest's collared neck and full zip closure, you'll stay warm, and it's the perfect layering piece for cooler days.

$45 $40

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Levi's Men's Original Trucker Jacket

Levi's Men's Original Trucker Jacket
Amazon

Levi's Men's Original Trucker Jacket

Sometimes the situation calls for a trucker denim jacket. 

$90 $80

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Tommy Hilfiger Men's Undershirts 3 Pack Cotton Classics V-Neck T-Shirts

Tommy Hilfiger Men's Undershirts 3 Pack Cotton Classics V-Neck T-Shirts
Amazon

Tommy Hilfiger Men's Undershirts 3 Pack Cotton Classics V-Neck T-Shirts

Tommy Hilfiger's 100% cotton V-neck tees are a bestseller thanks to their soft fabric and simple silhouette.

$46 $23

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Van Heusen Men's Short Sleeve Dress Shirt

Van Heusen Men's Short Sleeve Dress Shirt
Amazon

Van Heusen Men's Short Sleeve Dress Shirt

Available in plenty of stylish colors, this short-sleeve dress shirt is a fall staple.

$26 $20

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Lacoste Mens Long Sleeve Crew Neck Regular Fit Sweater

Lacoste Mens Long Sleeve Crew Neck Regular Fit Sweater
Amazon

Lacoste Mens Long Sleeve Crew Neck Regular Fit Sweater

Crafted from 100% organic cotton jersey, this timeless ribbed crew neck sweater from Lacoste provides year-round softness.

$130 $70

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The Best Amazon Deals on Men's Pants

Amazon Essentials Men's Slim-Fit Flat-Front Dress Pant

Amazon Essentials Men's Slim-Fit Flat-Front Dress Pant
Amazon

Amazon Essentials Men's Slim-Fit Flat-Front Dress Pant

An affordable pair of dress pants perfect for any fall occasion. 

$30 $24

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Levi's Men's 511 Slim Fit Jeans

Levi's Men's 511 Slim Fit Jeans
Amazon

Levi's Men's 511 Slim Fit Jeans

These classic Levi's jeans are bestsellers for a good reason.

$70 $39

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Amazon Essentials Men's Stretch Chino Pant

Amazon Essentials Men's Stretch Chino Pant
Amazon

Amazon Essentials Men's Stretch Chino Pant

Made with 72% organic cotton, these slim-fit chino pants are designed for all-day comfort.

$31 $25

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Levi's Men's 505 Regular Jeans

Levi's Men's 505 Regular Jeans
Amazon

Levi's Men's 505 Regular Jeans

Grab Levi's essential 505 jeans to pair with t-shirts, button-downs, sweaters and just about every other type of shirt. 

$70 $40

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Champion Men's Everyday Fitted Ankle Cotton Pants

Champion Men's Everyday Fitted Ankle Cotton Pants
Amazon

Champion Men's Everyday Fitted Ankle Cotton Pants

This Amazon best-seller will keep your comfortable all day long.

$30 $23

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Adidas Men's Aeroready Essentials Tapered Cuff Woven 3-Stripes Pants

Adidas Men's Aeroready Essentials Tapered Cuff Woven 3-Stripes Pants
Amazon

Adidas Men's Aeroready Essentials Tapered Cuff Woven 3-Stripes Pants

Adidas' 3-Stripes Tapered Pants feature AEROREADY to manage your body's moisture and keep you dry on warmer days. 

$50 $40

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The Best Amazon Deals on Men's Shoes

Adidas Originals Men's Stan Smith Sneaker

Adidas Originals Men's Stan Smith Sneaker
Amazon

Adidas Originals Men's Stan Smith Sneaker

You can never go wrong with a classic pair of Adidas Stan Smiths.

$100 $52

Shop Now

Cole Haan Men's Grandpro Rally Canvas Court Sneaker

Cole Haan Men's Grandpro Rally Canvas Court Sneaker
Amazon

Cole Haan Men's Grandpro Rally Canvas Court Sneaker

These colorblock sneakers have a rubberized EVA outsole for durability and a nice soft sole that's good for walking and great for casual wear.

$85 $44 and up

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Under Armour Men's Charged Assert 9 Running Shoe

Under Armour Men's Charged Assert 9 Running Shoe
Amazon

Under Armour Men's Charged Assert 9 Running Shoe

Soft shock absorption, a breathable mesh upper and a cushioned midsole provide plenty of comfort and support in a stylish package.

$70 $55

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Adidas Men's Pureboost 22 Running Shoe

Adidas Men's Pureboost 22 Running Shoe
Amazon

Adidas Men's Pureboost 22 Running Shoe

The Adidas Pureboosts help to provide all-day comfort — whether you're gearing up for a major workout or just heading back into the office for work.

$140 $49

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Cole Haan Men's Grand Crosscourt II Sneakers

Cole Haan Men's Grand Crosscourt II Sneakers
Amazon

Cole Haan Men's Grand Crosscourt II Sneakers

Made of genuine leather, these Cole Haan shoes give off a dressier look while offering all the comfort of sneakers.

$110 $90

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Brooks Men's Ghost 14 Neutral Running Shoe

Brooks Men's Ghost 14 Neutral Running Shoe
Amazon

Brooks Men's Ghost 14 Neutral Running Shoe

Elevate your running experience with Brooks Ghost 14 running shoes that feature 3D FIt Print technology to provide stretch and structure. 

$140 $83

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Reebok Men's Club C 85 Sneaker

Reebok Men's Club C 85 Sneaker
Amazon

Reebok Men's Club C 85 Sneaker

White sneakers are a versatile wardrobe staple, and these quintessential Reeboks offer superior comfort.

$75 $56

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The Amazon Prime Big Deal Days sales don’t stop here! Check out our guide to all the best October Prime Day deals to shop before the holidays begin.

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