Amazon Prime Men’s Underwear: What to Buy Prime Day 2025

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Top Amazon Prime Men’s Underwear Deals

Table of Contents

• Introduction to Amazon Prime Day
• What are the Amazon Prime Men’s Underwear Deals?
  • Men’s Briefs
  • Men’s Boxer Briefs and Trunks
  • Men’s Boxer Shorts
  • Men’s Jockstraps and Thongs

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What is Amazon Prime Day?

Amazon’s Prime Days, taking place from July 8 to 11, 2025, are an excellent opportunity to stock up on essentials, including men’s underwear. If you’re not familiar with Prime Day, it’s Amazon’s annual sale days, during which many products are deeply discounted. 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 Unlimited Streaming of Amazon Prime Video and Music
• Free Grubhub+
• Plus other benefits

Note that the prices shown below are *not* the prices for Prime Members. You’ll need to click on the buttons to see the discounted Prime price direct on Amazon’s site.

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 an excellent opportunity to try out new types and styles of underwear without breaking the bank. 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 making a comeback in style. Many more brands offer men’s briefs, and an increasing number of men are either switching to briefs or incorporating them into their underwear collections. And I don’t mean old-school, 100% cotton tighty-whiteys – even men’s white briefs are fashionable today.

What makes today’s briefs more fashionable are that they are “hip cut,” meaning the fabric only covers part of your hip, unlike traditional full-cut briefs (“tighty-whiteys”). 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 or bikini briefs instead. Tanga briefs don’t have any hip coverage, so they are both sexier and cooler in warm weather at the same time. On the other hand, Bikini briefs are often low-rise and have a thin piece of fabric along the hip.

Bamboo Cool Bamboo Briefs

I love modal and bamboo underwear! They are my favorite materials because they are so soft, cooler than cotton, and they feel awesome. So when you can get quality bamboo underwear on sale, you need to stock up! For Prime Day, you can buy Bamboo Cool briefs for $6-7/pair, which is awesome.

Bamboo Cool makes a lot of bamboo-based men’s underwear. What I really like about Bamboo Cool is that they provide 8% Spandex content in their bamboo underwear, whereas many cheap brands only provide 5% or less. That extra 3% adds a bit more flexibility to the fabric, creating a more comfortable wearing experience.

Note that Bamboo Cool also makes a polyester-bamboo blend line of underwear. I recommend you stick with the 92% Viscose (Bamboo)/8% Spandex blend, so make sure you check the fabric content before ordering.

Last update on 2025-07-14 at 08:04 / Affiliate links / Images from Amazon Product Advertising API

David Archy Bamboo Briefs

I have owned three bamboo briefs from David Archy’s sister company, Separatec, for years now, and they are awesome (you can read my review here). The only difference between Separatec and David Archy is that Separatec has a Dual Pouch system, where as David Archy uses a regular pouch that most guys are used to.

David Archy has their bamboo hip briefs on sale for Prime Days! If you buy a seven-pack as shown below, the price is below $6/pair with Prime. If you buy three packs – that is 21 pairs – you’ll have plenty for three weeks of daily wear! Just note that some models have a fly and others don’t have a fly, so make sure you get what you want!

Last update on 2025-07-13 at 08:30 / Affiliate links / Images from Amazon Product Advertising API

Wirarpa Modal Hip Briefs

These Wirarpa modal hip briefs are an excellent value for less than $5/pair. That is awesome for modal briefs, which are one of my two favorite underwear fabrics (bamboo is the other). They get 4.5/5 stars on Amazon with over 20,000 ratings, so these Wirarpa modal briefs are highly rated. Multiple colors are available, but note that there is no fly.

Last update on 2025-07-13 at 08:30 / Affiliate links / Images from Amazon Product Advertising API

Reebok Performance Low-Rise Briefs

At just over $3/pair and a 4.6 average rating on Amazon, it is hard to beat this 10-pack of polyester-based Reebok Performance low-rise bikini briefs. I love that they come in all-black or various black and bright colors so you can spice up your underwear collection. With a perfect combination of sportiness and sexiness and a fantastic price, you can’t go wrong with these Reebok briefs.

Last update on 2025-07-13 at 08:30 / Affiliate links / Images from Amazon Product Advertising API

Separatec Dual Pouch Tanga Briefs

I have worn Separatec’s Dual Pouch underwear for several years and I love the Dual Pouch. If you aren’t familiar with it, read my full review here. It is quite difficult to find men’s pouch underwear for less than $10 per pair; even harder to find separated pouch briefs. But you can get Separatec’s bamboo tanga briefs for $10/pair, which you should try out.

Last update on 2025-07-13 at 08:30 / Affiliate links / Images from Amazon Product Advertising API

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.
• In the United States, boxer briefs with 4″-6.5″ inseams are standard. Most boxer briefs, especially those with 5-6″ inseams, fall into this category.
• 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.

Calvin Klein Micro Stretch Low Rise Trunks & Boxer Briefs

I have been a long-time fan of Calvin Klein’s microfiber underwear, which includes trunks and boxer briefs. Amazon has them on sale for dirt cheap prices, especially the medium Micro Stretch boxer briefs. That is an excellent deal for Calvin Klein non-cotton underwear (please don’t compare these to your cheap CK Cotton Classics!). 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. Or if you are good with your well-known boxer briefs, go for that too!

Last update on 2025-07-14 at 04:20 / Affiliate links / Images from Amazon Product Advertising API

Last update on 2025-07-13 at 10:53 / Affiliate links / Images from Amazon Product Advertising API

Jockey Modal Boxer Briefs – 6″ and 9″ Inseam

I love modal and previously reviewed Jockey 6″ modal boxer briefs. They are perfect for everyday wear and lounging around. I own two pairs, and I love them both! I purchased mine during a blowout sale, and with Amazon Prime Day, you can get amazing pricing too!

Amazon has both the 6″ and 9″ long-leg three-packs on sale. You can get the 6-inch modal boxer briefs on sale for $4/pair, which is an absolute steal. The 9-inch boxer briefs are around $10/pair in a three-pack, but some of the color and size combinations are as low as $4/pair. Getting high-quality modal boxer briefs for under $10/pair is an amazing deal!

Last update on 2025-07-13 at 08:41 / Affiliate links / Images from Amazon Product Advertising API

Last update on 2025-07-13 at 08:41 / Affiliate links / Images from Amazon Product Advertising API

Under Armour BoxerJock Boxer Briefs

If you prefer microfiber boxer briefs—especially for gym workouts, outdoor activities, and high-sweat work—Under Armour’s BoxerJocks are at blowout prices at less than $7/pair. There are so many fun colors and patterns to choose from, which I love. I own a pair of Under Armour 6″ boxer briefs (called BoxerJocks), and you can read my Under Armour review here. And don’t take my word for it – these 6-inch and 9-inch BoxerJocks have a 4.7 rating on Amazon!

Last update on 2025-07-14 at 02:57 / Affiliate links / Images from Amazon Product Advertising API

Last update on 2025-07-13 at 08:46 / Affiliate links / Images from Amazon Product Advertising API

Calvin Klein Modal Boxer Briefs

Calvin Klein’s modal boxer briefs were some of the first CK boxer briefs I bought – over 15 years ago. I still love them to this day! You can read my complete review of CK modal boxer briefs here. Amazon has them on sale for $13/pair in three-packs. The CK modal boxer briefs are thinner and feel more luxurious than the Jockeys, but obviously you are paying a higher price for them.

Last update on 2025-07-13 at 12:10 / Affiliate links / Images from Amazon Product Advertising API

Tommy John 360 Sport Trunks

I bought a bunch of Tommy John underwear earlier this year, including a pair of 360 Sport Trunks. I love them! The polyester material is smooth and silky blended with 12% Spandex content (I require a minimum of 10%). They look awesome, feel extremely comfortable, and the horizontal fly is wonderful for guys wanting a fly. Note that these trunks are 4″, which are really just shorter boxer briefs.

Tommy John underwear is expensive usually, but I found these for 30% off! If you are unfamiliar with Tommy John, read my Complete Guide to Tommy John Underwear here. Note that I believe Tommy John has the best men’s underwear fly out there.

Last update on 2025-07-13 at 08:58 / Affiliate links / Images from Amazon Product Advertising API

Last update on 2025-07-13 at 08:46 / Affiliate links / Images from Amazon Product Advertising API

Hanes X-Temp Boxer Briefs & Trunks

If just love your Hanes, then I’d prefer you at least get the Hanes X-Temp Boxer Briefs or Trunks with the Total Support Pouch. I recently purchased a three-pack and was pleasantly pleased, especially for the price. Read my full review of Hanes’ Total Support Pouch here. Note that the Total Support Pouch is available in X-Temp trunks, boxer briefs, and long-leg boxer briefs, allowing you to choose the style you love. For less than $5/pair with Prime, these boxer briefs with a separated pouch are tough to beat.

Last update on 2025-07-13 at 10:10 / Affiliate links / Images from Amazon Product Advertising API

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. 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 these David Archy bamboo boxers (I own many David Archy and Separatec underwear – love them all!).

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.

Last update on 2025-07-13 at 10:53 / Affiliate links / Images from Amazon Product Advertising API

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!

Papi 100% Cotton Jockstraps

Even though I am not a fan of cotton underwear, I can’t ignore the exceptional price of this three-pack of Papi jockstraps. Getting a three-pairs of sexy Black Papi jockstraps for less than $4/pair is a steal – some sizes are as low as $2-3/pair! I love the colors, including sophisticated black, sporty red, and a cool blue color, but the colors are more expensive.

Last update on 2025-07-13 at 08:58 / Affiliate links / Images from Amazon Product Advertising API

Summer Code Nylon Jockstraps

Picking up jockstraps for $5/pair is an amazing deal, especially ones with a silky 85% nylon/15% Spandex fabric blend. These Summer Code jockstraps fit the bill and won’t blow your budget either. I also appreciate that they have several colors to choose from, including black, orange, and green.

Last update on 2025-07-13 at 19:12 / Affiliate links / Images from Amazon Product Advertising API

IKINGSKY T-Back Thongs

I am not a fan of thongs. I own two thongs, and I just can’t wear them as my skin gets irritated. But many guys love thongs for their freedom and extreme sex appeal. I have spoken to many thong-loving guys, and one name keeps getting recommended: IKINGSKY. Many guys love IKINGSKY thongs, and likewise, Amazon customers give them a 4.5 rating with over 1,400 reviews.

IKINGSKY doesn’t have a sale on these for Prime Day. However, if you are ordering other underwear and want to try out some men’s thongs, might as well add these to the cart and see how you like them. The regular price is already an amazing deal!

Last update on 2025-07-13 at 08:58 / Affiliate links / Images from Amazon Product Advertising API

Summary of the Amazon Prime Men’s Underwear Deals

Amazon’s Prime Days event is upon us here in July 2025, so bookmark this page to see all of the great deals. And 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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