Wednesday, October 8, 2025

Best Men’s Clothing and Shoe Deals for Prime Day

Even though it’s a relative newcomer, Amazon’s October Prime Day sale has turned out to be one of the biggest shopping events of the year. From October 7 to 8, Amazon is offering discounts nearly as deep as those on Black Friday. While it’s a go-to for tech and home goods, it’s also a great time to score bargains on men’s fashion.

Whether you’re restocking essentials like socks and underwear or revamping your fall wardrobe, the sale has something for you. From rugged denim to cozy sweatshirts and comfortable sneakers, we’ve gathered top deals you won’t want to miss. If you’re looking for more discounts, check out our roundup of the best Prime Day deals across all categories.

Best Prime Day men’s clothing deals

We’ve rounded up the best deals on men’s clothing from brands you know and love like Levi’s, plus some great-priced basics.

levi's trucker thumb

Levi’s Men’s Trucker Jacket

The Levi’s Trucker Jacket is the quintessential denim jacket. It comes in a variety of washes and is also available in big and tall sizes.

Champion Men's Pullover Hoodie

Champion Men’s Pullover Hoodie

This sporty classic is a timeless streetwear piece that is just as cozy as it is cool. It comes in over a dozen colors and big and tall sizes.

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COOFANDY Zipper Polo Shirt

This knit polo with a zipper detail is trendy enough to look modern but classic enough to pair with anything.

Ultimate Chinos

Dockers Ultimate Chinos

The four-way Smart 360 Flex™ material on these stretchy chinos makes for a comfortable men’s work pant.

Levi's Men's 505 Regular Fit Jeans

Levi’s Men’s 505 Regular Fit Jeans

We love Levi’s jeans — not just because they fit well and are a classic — but also because they last a super long time. These stylish and durable jeans are available in both regular and tall fits.

Men’s shoes

There are lots of men’s shoes on sale for Prime Day, many of them from classic and coveted brands like Adidas. There are also Cole Haan sneakers, which we love for comfortable work shoes, that you can get for a discount.

Cole Haan Men's Grand Crosscourt II on a white background.

Cole Haan Men’s Grand Crosscourt II

Featuring a smooth leather upper and classic cup sole, the Cole Haan Grand Crosscourt II is a casual sneaker that can be dressed up or down.

Unisex Adult Daily

Adidas Unisex Adult Daily

These classic Adidas sneakers are available in many neutral colors, such as beige, grey, black, olive, and more.

adidas

adidas Men’s Kaptir 3.0 Shoe

This popular Adidas sneaker model has a thick outsole for maximum shock absorption but is still incredibly lightweight.

Men’s accessories

If you’re always searching for a belt or a matching pair of socks, this is a great time to make sure you have everything you need for the next time you have a wedding to attend or a nice dinner to go to.

FAQs

Is Prime Day a good time to buy clothes and shoes?

Yes, Amazon has great deals on clothes and shoes year-round, but we’ve seen significantly lower prices during shopping holidays like Prime Day.

What are the best clothing items to shop for during Prime Day?

Amazon Prime Day is a great chance to stock up on the essentials you need. Some of the best deals include items like underwear, T-shirts, and socks. For seasonal items, you’ll find fall fashion must-haves like jeans, sweatshirts, and boots. There are also many deals on office staples, such as oxfords, and casual pieces like sweatpants and hoodies.

Shopping for more discounts today? Check out our roundup of all of the best Prime Day deals, or browse Amazon’s website for the full selection.

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Disclosure: Written and researched by the Insider Reviews team. We highlight products and services you might find interesting. If you buy them, we may get a small share of the revenue from the sale from our partners. We may receive products free of charge from manufacturers to test. This does not drive our decision as to whether or not a product is featured or recommended. We operate independently from our advertising team. We welcome your feedback. Email us at reviews@businessinsider.com.



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