Buying Men’s Underwear in Three Simple Steps (Shopping Guide)

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Buying men’s underwear is quite fun for me. Yet, many guys don’t find it as fun as I do – booo! Nonetheless, purchasing comfortable underwear is essential, and I want to make the process easy!

Below is my three-step plan for buying men’s underwear quickly and efficiently while still finding your ideal underwear. All you have to do is look at the three categories – style, fabric, and fly preference – and choose which one (or multiple selections) in each category works best for your preferences and use. Once you combine all three choices, you are good to go!

If you have any questions on buying men’s underwear, leave a comment below so I can better assist. 🙂

Watch the video for the tips and then use the rest of this blog post to Find Your Ideal Underwear.

Step 1 for Buying Men’s Underwear: When are you wearing your new underwear?

Business or business-casual work environment, relaxing on hot days, or sexy date nights: wear Briefs.

  • Many millennials may hesitate to buy briefs due to the stigma associated with them from the 1990s and 2000s, when we grew up. Yet as I note in my blog post regarding modern men’s briefs, we’re grown up now, and briefs are surging in popularity. Briefs are fantastic paired with suit pants, relaxing on hot days, and sexy date nights. And briefs provide a raw sex appeal that boxer briefs and trunks can’t match.
    • If you are switching from boxer briefs to briefs, consider trying trunks first to get used to how short briefs are. This in-between step is especially true if you hang out often in your underwear.

Athletes, gym sessions, hiking, and traveling underwear: wear polyester/nylon blended boxer briefs or long-leg boxer briefs

  • Guys who will be heavily sweating and prone to skin irritation may want long-leg boxer briefs. Coming with a 7” to 9” inseam (regular boxer briefs are 4” – 6” inseam), long-leg boxer briefs provide better protection between your legs and the material of your shorts. Also, if you get moisture-wicking fabric, long-leg boxer briefs assist sweat protection and cooling. If you don’t have problems with skin irritation or don’t want the extra length, athletic boxer briefs work just as well.
Comparison of 4 inch, 6 inch, and 8 inch men's boxer briefs.
Comparison of 4-inch, 6-inch, and 8-inch men’s boxer briefs.

Chillaxing on weekends and hanging out in only your underwear: wear bamboo or modal boxer briefs and trunks

  • I love hanging out in bamboo and modal boxer briefs or trunks. The material is so soft, and boxer briefs and trunks provide suitable coverage that I don’t mind being seen by pesky neighbors.
    • Additionally, boxer briefs provide suitable performance in all situations, from heavy sweating during sports to chillaxing all day at home. So if you aren’t sure what to pick, you can’t go wrong with a fantastic pair of bamboo or modal boxer briefs and trunks.
    • And don’t forget to read my shopping guide for the Best Boxer Briefs on Amazon to Find Your Ideal Pair quickly.
  • If you require modesty, such as having kids or nosy neighbors, boxer shorts substitute well for boxer briefs for lounging. Since boxers are just shorter shorts, you won’t have to worry about being “exposed.”
    • Some brands advertise their boxer shorts as “slim-fit,” which I don’t like. While slim-fit boxers look more modern, they don’t provide a lot of roominess that guys love about boxers. If you want slim-fit, go with boxer briefs; buy a “real” pair of boxers if you desire boxer shorts.

Chill Boys Performance Boxers - Cool, Soft, Breathable Men's Boxers

Lounging requires soft and comfy boxers like from Chill Boys, rather than cheap, stuffy polyester boxers.


Everyday underwear or not sure what to buy: wear trunks

  • I could have easily mentioned boxer briefs and briefs in the “everyday underwear” category. Yet, I’d opt for trunks to make this simplistic, especially if you aren’t particularly sure what style you want. 
  • Trunks are shorter boxer briefs, providing less leg coverage (often half as much as boxer briefs or less). I encourage guys wearing boxer briefs to try out trunks because they have less leg fabric to allow greater air circulation and less material to bunch up. And for me, trunks are sexier than boxer briefs. Trunks are also very common in the rest of the world, especially in Europe (known as “boxers” in Europe).
    • Be careful in choosing trunks, as they often come in two flavors: trunks and “square-cut trunks.” I recommend 2-3” inseam trunks because they function well as shorter boxer briefs. Square-cut trunks are often 1” inseam and, to me, are too short as trunks and too long as briefs. If you wear square-cut trunks, I believe you are better off wearing briefs.

Raw sex appeal: wear Jockstraps

  • Once relegated to the locker rooms and gay culture, jockstraps may be starting to have their 15 minutes of fame. Some guys wear them as regular underwear, but I only wear jockstraps for special occasions. Why? Jockstraps are a massive turn-on for me! A guy’s bare butt exposed yet having their penis and balls covered up is exhilarating. Plus, as a bottom, I can have sex while wearing underwear, which is fantastic since I love sex and wearing underwear. I can combine both experiences into one!

Other niche styles: bikini briefs, anti-pouch kilts, thongs, and so on…

  • I need to experiment with these niche underwear styles. (One exception is the anti-pouch Boxerkilt, which you can read my review here.) Feel free to ask me in the comments or email me with what you’d like me to review for you!


Step 2: How to choose the right material when buying men’s underwear

Heavy sweat situations, gym sessions, water-based activities, hiking, traveling: wear Polyester or nylon-based blend.

Everything else: wear bamboo or modal

  • If you have read any other part of my blog, you’ll know my love for bamboo and modal underwear. Softer and sturdier than cotton, far more breathable than polyester/nylon, and more environmentally friendly than both materials, I believe bamboo and modal are the best fabrics for men’s underwear.
    • Most bamboo and modal men’s underwear contains 5% spandex or elastane. You’ll want to stick with 5% or higher for comfort (some brands go as low as only 2% spandex or elastane). Premium brands may offer 7-10% spandex/elastane content. High spandex/elastane is more luxe, yet you also don’t need to splurge for greater than 5% with modal and bamboo underwear.
  • Sample selections:

Reviewing David Archy’s Bamboo Boxer Briefs


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Step 3: How do you pee?

You don’t use your pants’ fly: wear no-fly underwear.

  • Why bother with a fly on your underwear if you don’t even use the fly on your pants? No-fly men’s underwear is more common nowadays as, without a fly, the pouch will be roomier. And since getting a fly isn’t the end of the world, you’ll have the most comprehensive selection to choose your next pair of men’s underwear.

You use your pants’ fly: wear vertical-fly underwear.

If you aren’t sure what type of fly you want, watch my YouTube video on Common Men’s Underwear Fly Types.

Buying Men’s Underwear in Three Simple Steps

Many guys and their partners may not know the best way of buying men’s underwear. Following the three-step process above will make it easier to narrow down your choices and zone in on what kind of underwear a guy needs for specific occasions or everyday wear. 

  • What style works best for you and the occasion: business, leisure, relaxation, outdoor activities, date nights, etc. If you aren’t sure, I believe briefs or trunks are best for working, lounging, and everyday wear. For work outs, hiking, and other sports, wear boxer briefs or long-leg boxer briefs.
  • What fabric or material is necessary for the job: natural bamboo or modal, or synthetic materials like polyester and nylon. Bamboo and modal are far superior to cotton for everyday wear, while polyester and nylon is great for moisture wicking during intense activities or when in the water.
  • How do you pee? If you like using a fly, buy vertical-fly underwear. If you don’t use a fly or don’t care, buy no-fly underwear.

Let me know in the comments your questions about buying new men’s underwear and how you choose what underwear to purchase!


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Eric at MensUnderwearGuide.com

Eric is the creator and writer of MensUnderwearGuide.com. 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.

Comments 4

  • Bow CrosbyJanuary 29, 2023 at 12:29 pm

    I just subscribed to your website. Great reading!!!
    Like you, I have gone thru the underwear trends and currently wear boxer briefs with pouch.
    I also occasionally wear thongs (mens styles, not ladies) which I really enjoy and find extremely comfortable. Do or have you ever worn thongs? Any plans to review?

    My main question for you is: I sweat a lot, to the point that I often get rashes in my crotch, and often, these areas get totally raw, requiring a Rx to cure the rash. I do keep this area extremely clean and use powder in the area based on recommendations from my dermatologist. What would be your recommendations for the best boxer briefs to try to minimize my rashes. I currently wear Obviously most often and have a few David Archy boxer briefs, not dual pouch.
    Thanks and I look forward to reading what you have to say.
    BTW, my equipment is on the small size and I am a senior citizen.

    • Eric at MensUnderwearGuide.comFebruary 1, 2023 at 9:26 am

      Hello Bow,

      Thank you for reading my blog! I appreciate it!

      I have one mesh thong, but I find it uncomfortable to wear. I really don’t like the fabric in between my butt cheeks and it causes irritation in that area. I may try another thong in the future, so if you have any recommendations, please let me know!

      Instead of thongs, I like wearing a jockstrap to bed sometimes or for sex. I also got my first bikini/tanga brief that I really enjoy. You can see it here:
      https://youtu.be/6VdDKYEUbMA

      As far as your issue, I am sorry you are going through that. I would have recommended a light bamboo or modal boxer brief, but I see you have that covered with Obviously and David Archy (assuming you have a bamboo or modal David Archy pair).

      Have you tried any moisture-wicking polyester-based boxer briefs? I really like Mack Weldon’s AirknitX lineup, although they are a bit pricey at $32/pair. But I think they are the best value of Mack Weldon underwear.

      For a cheaper alternative, I like my Puma Performance Boxer Briefs. You can usually get a 3-pack for around $20 on Amazon. They aren’t mesh, but they are polyester-based and dry quickly. Make sure you get the 85% polyester version, not the 90% version.

      One question I have for you is do you get rashes while wearing thongs? If not, why not wear them all the time? I know there may be professional reasons or hygiene reasons (you don’t sweat all over your pants, for example), but curious to know.

  • Alex ScottMarch 10, 2023 at 1:10 pm

    All you have to do is look at the three categories style, fabric, and fly preference. The way the rest of the underwear fits you depends greatly on the brand. Thanks for coming up with these tips.

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