Amazon Prime Men’s Underwear: What to Buy Prime Day 2023

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*My note:* Amazon Prime Day July 11-12, 2023 is over. However, the next Amazon Prime Days will be in October 2023, according to one of Amazon’s executives in this LinkedIn post. They are calling it Amazon Prime “Big Deal Days.” I will update this page during that event and Black Friday/Cyber Monday November 24-27, 2023. Keep this website bookmarked, and subscribe to my email newsletters to stay informed on sales!

Top Amazon Prime Men’s Underwear Deals

Table of Contents

What is Amazon Prime Day?

Amazon’s Prime Day is an amazing time to stock up on essentials from Amazon, including men’s underwear! If you don’t know what Prime Day is, it is Amazon’s annual two-day sale in which many products are deeply discounted. But it is called Prime Day because the sales are only available to Amazon Prime members. If you aren’t a Prime member, you can get a free 30-day trial using this link, which is perfect for Prime Day!

With Amazon Prime, you get the following additional benefits besides member-only deals:

  • Free same-day, one-day, and two-day shipping on many purchases from Amazon
  • Free shipping on $150+ purchases at Amazon Fresh stores
  • Free Amazon Prime Video and Music
  • Free Prime Try Before You Buy

This year, Prime Day was Tuesday-Wednesday, July 11-12, 2023, so the sales are over, unfortunately.

What are the Amazon Prime Men’s Underwear deals?

I’ll break down the deals by men’s underwear style, making it easier to navigate. But don’t just buy the underwear styles you are used to! Amazon Prime Day is a great time to experiment with new underwear types and styles without costing a fortune. Learn more about different underwear styles in my Guide to Men’s Underwear Styles.

Amazon Prime Deals for Men’s Briefs

In case you haven’t noticed, men’s briefs are back in style. Many more brands offer men’s briefs, and many more guys are either switching to briefs or including them as part of their underwear collection.

Note that modern briefs are “hip cut,” meaning the fabric only covers part of your hip, unlike traditional full-cut briefs. Generally, hip briefs are what you would want to purchase unless you are into full-cut traditional briefs. More adventurous guys may opt for tanga briefs instead. Tanga briefs don’t have any hip coverage, so they are both sexier and cooler in warm weather at the same time.

Wirarpa Modal Hip Briefs

These Wirarpa modal briefs on sale are good value for around $6/pair. That is awesome for modal briefs, which is one of my two favorite underwear fabrics (bamboo is the other). They get 4.5/5 stars on Amazon with over 17,000 ratings, so these Wirarpa modal briefs are highly rated. Multiple colors are available, but note that there is no fly.

Calvin Klein Micro Stretch Hip Brief

Calvin Klein microfiber underwear is amazing – I got my first pair over 12 years ago! But I paid closer to $20/pair! Note that they have an 88% Polyester/12% Elastane fabric blend, which is smooth and soft. They look sophisticated and sexy! Note that they don’t have a fly.

Evolve No-Show Hip Briefs

These Evolve “No-Show” briefs look quite intriguing for the price. I love that they are hip-briefs and that the Micro Sport version looks sporty. The Micro Sport version is 90% polyester and 10% Spandex, which meets my criteria of at least 10% Spandex content in polyester underwear. Evolve also has a softer viscose version of 95% viscose and 5% Spandex content, which is also good.

Avidlove Classic Bikini Briefs

More adventurous guys may opt for bikini or tanga briefs instead (both terms are interchangeable for men). Bikini/Tanga briefs don’t have any hip coverage, so they are both sexier and cooler in warm weather at the same time compared to hip briefs, especially compared to full-cut briefs.

So if you love bikini/tanga briefs, or want to experiment with this short style, picking up a four-pack of Avidlove bikini briefs is an interesting option. I don’t have any personal experience with them, but with great reviews, an 87% nylon/13% Spandex fabric blend, and an array of spicy colors, I doubt you can go wrong with these bikinis.

Colorfulleaf Bamboo Briefs

Colorfulleaf seems to be a new men’s underwear company, as I just started seeing their underwear on Amazon. They sell this three-pack of men’s bamboo hip briefs for an amazing price so I wanted to mention it. With such a low price, it might be worth checking them out – and if you do, leave a comment so I know how they are!

Amazon Prime Deals for Men’s Boxer Briefs and Trunk Underwear

Most men in the United States wear boxer briefs, although some guys are switching to trunks. The key with boxer briefs is to know your inseam length or the length of the legs from your crotch to the bottom of your boxer briefs. As a recap:

  • 1-2″ inseams are “square-cut” trunks. These trunks are square-ish looking because the legs don’t come down much. Square-cut trunks are more popular outside of the US than in the US.
  • 2-4″ inseams are American-style trunks. These are my favorite type of underwear and a great alternative to boxer briefs.
  • 4-6.5″ inseams are standard boxer briefs in the United States. Most boxer briefs fall into this category, especially 5-6″ inseams.
  • 7-9″ inseams are Long-Leg Boxer Briefs. Long-leg boxer briefs are better for guys with thicker thighs who suffer from riding up or skin irritation (chafing). Or they are also great for athletes and workouts or during colder seasons to provide greater warmth to your thighs.

Colorfulleaf Bamboo 2.5″ Trunks

In addition to their bamboo briefs, Colorfulleaf is also selling their bamboo trunks at good prices (varies based on color and size). With great ratings, I would definitely try their bamboo trunks! (Bamboo is one of my two favorite underwear materials!)

(If you are a size small, they also have their 5.5″ boxer briefs on sale too!)

Calvin Klein Micro Stretch Low Rise Trunks

I have been a big fan of Calvin Klein microfiber underwear for many years, including trunks and boxer briefs. I found this three-pack of Calvin Klein Micro Stretch Low Rise trunks and also this you five-pack (note the colors on the five-pack)! That is an excellent deal for Calvin Klein non-cotton underwear. If you have been wearing boxer briefs but want to try something shorter and sexier without buying briefs, these Calvin Klein trunks are a great starting point.

Jockey Modal Boxer Briefs – 6″ and 9″ Inseam

I love modal and previously reviewed Jockey 6″ modal boxer briefs. I own two pairs, and I love them both! I purchased mine during a blowout sale, and with Amazon Prime Day, now you can get amazing pricing too!

Jockey modal boxer briefs blog review header

Amazon has both the 6″ and 9″ long-leg three-packs. Pricing depends on your size and the color combination. The best pricing seems to be this black/gray/red color combination (6″ version and 9″ version links). Getting high-quality modal boxer briefs for under $10/pair is an amazing deal!

Separatec 8″ Long-Leg Boxer Briefs

Long-leg boxer briefs are great for men who want to wear boxer briefs but have problems with boxer briefs riding up. Or for men with irritated skin – “chafing” – on their legs and thighs and need underwear to protect the area. I have previously reviewed Separatec’s long-leg boxer briefs, which I love.

However, note that all Separatec underwear includes Separatec’s Dual Pouch system. Read my Separatec review for full details on this unique pouch design, where I discuss the Dual Pouch system.

David Archy Bamboo Boxer Briefs

Besides Jockey modal boxer briefs, I also really enjoy David Archy’s Bamboo Boxer Briefs. These 5.5″ boxer briefs look great, have a fly, and are so soft against the skin. This is a great time to stock up on these boxer briefs. Also, if you wear trunks, you can get a seven-pack of bamboo trunks.

Header for my blog post reviewing David Archy boxer briefs

Youlehe Stretch Trunks

I don’t know anything about Youlehe other than they sell quite a bit of underwear on Amazon. I thought this eight-pack of trunks was quite intriguing. Amazon customers rate it quite positively. I am a huge fan of bamboo underwear, so these trunks that are 95% bamboo and 5% Spandex meets my criteria.

Amazon Prime Deals for Men’s Boxer Shorts

Some men still prefer the roominess of men’s boxer shorts, although men’s boxers may be more popular with women than men. Men’s boxer shorts are great for hanging out, sleeping, and general lounging, but I’d avoid boxer shorts for officewear.

David Archy Bamboo Boxer Shorts

I wrote previously about David Archy’s bamboo boxer briefs, which I love. I also greatly enjoy David Archy’s sister brand Separatec and their bamboo briefs. But I don’t have any boxers from David Archy or Separatec because I don’t wear boxer shorts. But if you do, you may want to check out this three-pack of David Archy bamboo boxers

Note that it comes with a button fly, which is great, but the inseam is 6.5″ long. This is a bit long for boxers and would work better if you intend only to wear boxers, such as lounging around the house.

Amazon Aware Cotton-Modal Boxer Shorts

Many boxer shorts are 100% cotton or a cotton-polyester blend, especially if you buy cheap boxers. But these Amazon boxers are a 58% cotton/38% modal blend (plus 6% elastane). Having 38% modal and 6% elastane should make these Amazon boxers very comfortable, especially if you are lounging around in them. I don’t wear boxers, so I can’t say how these are, but I also love that they are certified Carbon Neutral!

Amazon Prime Deals Men’s Jockstraps and Thongs

Let’s not forget an oft-forgotten part of men’s underwear: men’s jockstraps and thongs. While most people may associate jockstraps and thongs with sex, quite a few guys wear jockstraps and thongs as daily underwear. I have a couple of jockstraps, and I find jockstraps great to wear to bed. If you want to try spicing up your underwear and experiment with jockstraps and thongs, Amazon Prime Day is a wonderful time to try it!

Calvin Klein Micro Stretch Jockstraps

Amazon must have all of Calvin Klein’s Micro Stretch line because you can pick up this three-pack of CK jockstraps for a good price. That is another excellent value for high-quality, sexy jockstraps, especially if you want to try them out. Remember that jockstraps rarely have flys – and these Calvin Kleins do *not* have flys either.

Summary of the Amazon Prime Men’s Underwear Deals

Although Amazon Prime Days in July 2023 are over, keep this webpage bookmarked as I update it during October’s Amazon Prime event. But if you see a great deal, don’t wait! As so many others will be shopping on Amazon, you don’t want to return to your cart and find your great men’s underwear deal sold out. 🙁

Let me know in the comments what amazing Amazon men’s underwear deals you find!

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Eric is the creator and writer of He loves boxer briefs and trunks, exploring the new world of briefs, the soft feeling of modal and the lightness of mesh microfiber, and of course writing and researching the world of men's underwear.

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