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21 men’s clothing and shoe deals worth shopping this Prime Day

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21 men’s clothing and shoe deals worth shopping this Prime Day

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Amazon Prime Day has become a massive shopping event with deals similar to Black Friday and Cyber Monday. The shopping holiday historically happened only once a year in July, but Amazon is hosting a second Prime Big Deals Day event on October 8-9.

Prime Day is one of the best times of the year to shop for items like computers, Amazon devices, and home goods, but it’s also a great time to save on clothing and shoes.

Some of the best deals we’ve seen come from Amazon Essentials, as well as brands like Ralph Lauren, Champion, and Hanes.

Whether you need to replace basics like T-shirts and underwear or refresh your wardrobe with new styles for the fall and winter, you’ll find amazingly low prices on Amazon. To help you shop, we rounded up the best deals on men’s clothing, shoes, and accessories.

The best Amazon Prime Day deals on men’s clothing and shoes

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 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.

Adidas Samba


Adidas Samba

Originally designed for indoor soccer, the Adidas Samba has become one of The Three Stripes’ most iconic casual styles.

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.

socks saucony


Saucony Performance No-Show Socks

The six-pack of Saucony Performance No-Show socks will give you the most value for your money and keep your feet dry and comfortable.

Adidas Ultra Boost


Adidas Ultra Boost

The Adidas Ultra Boost is revered for its multi-use functionality. It’s built for running, but it’s also great for walking and casual wear.

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 during Prime Day?

Amazon Prime Day is a great chance to stock up on essentials you need regardless of a sale. Some of the best deals include items like underwear, T-shirts, and socks. There are also many deals on office staples like 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.

Amir Ismael author page picture

Amir Ismael

Editor, Insider Reviews

Amir Ismael is an editor for Insider Reviews, Insider’s e-commerce branch of the service journalism team.
As a collector of sneakers and fashion, Amir is passionate about all things related to style. He’s covered everything including the industry’s shift to producing more sustainable clothing, the most comfortable loungewear, all of the best places to shop for affordable business casual attire, and more. He’s used his expertise in footwear and the footwear industry to review all kinds of shoes from sportswear giants, well-known casual brands, and startups. Amir’s coverage also includes eyewear, watches, and grooming products like electric razors and men’s skincare.
Since the beginning of the coronavirus pandemic, Amir has led Insider Reviews’ face masks coverage with thoughtful recommendations based on CDC guidelines, expert opinions, and his own testing.
During his time at Insider, Amir previously handled deals of the day coverage, and worked as a generalist writing hundreds of reviews ranging from phone cases and headphones to bed sheets and blenders, and has also covered major shopping holidays including Amazon Prime Day, Black Friday, and Cyber Monday.
Before joining the Insider Reviews team in 2017, worked as a freelance writer for Complex Sneakers and Sole Collector where he contributed to daily sneaker news and release dates, feature-length articles, and interviews with artists, designers, and athletes. Amir graduated from William Paterson University in 2015 with a degree in journalism and public relations.
Say hello to Amir at aismael@businessinsider.com or on Instagram @amirjismael.
Learn more about how our team of experts tests and reviews products at Insider here.
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