Find Your Ideal Underwear

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Overwhelmed with the number of choices men have for underwear? Yearning for the simpler days of simply asking Boxers or Briefs? No need to panic! Finding the right pair of underwear doesn’t have to be hard.

Watch my video below on Three Simple Steps to Buying Men’s Underwear. Then keep reading to dive deeper into what criteria to look for when buying new men’s underwear.

Don’t find what you are looking for? Email me at with your ideal underwear criteria so I can find it for you!

All men’s underwear shares common features that using your past underwear experiences, combined with the knowledge you learned through my Ultimate Guides, will guide you to your ideal pairs of underwear. If you haven’t read my Ultimate Guides yet, I recommend you do so!


If you have already read my guides above, or you are an underwear aficionado yourself, I wrote a summary below of the key features to look for in men’s underwear.

Refresh Your Underwear Knowledge

  • Category: Select what style you are looking for. I categorize the following inseam lengths: Briefs (0″ inseam), Trunks (0 – 3.5″), Boxer Briefs (4″ – 6.5″), and Long Boxer Briefs (greater than 6.5″). While Boxer Briefs have dominated the market for the past decade, more and more guys are switching to trunks and briefs. If you are looking for underwear for high-intensity activities, you may want to choose Long Boxer Briefs to prevent chafing and rashes. And of course, you can also choose Boxer Shorts for those that prefer feeling those breezes!



  • Price: Price is king and while it is tempting to always choose the lowest price, you also get what you pay for. I often find that $15 to $25 per pair is the sweet spot for men’s underwear. However, I own some amazing pairs of underwear that I acquired for less than $10/pair, while there are some real clunkers in the $40+ range!
  • Primary Material: Gone are the days of wearing 100% cotton underwear. My favorite materials are modal and bamboo, as they are much lighter and softer than cotton, plus they are more environmentally friendly. Polyester, nylon, and polyamide are great for times when you need quick-drying underwear, such as at the beach or when hiking.
  • Color: When I was growing up, the white brief – “tighty-whiteys” – were the “standard” choice. Nowadays, I am pretty sure it is required for every guy to have a pair of black boxer briefs. I encourage all guys to spice up their underwear collection through diverse colors, patterns, and even images!
  • Fly: Functional flys mean you can pull your penis out to pee without pulling down your underwear. Most guys think of the Vertical Fly when they think of flys. However, a newer design is the Horizontal Fly, where you pull up on your penis, rather than to the side. There are plenty of brands that don’t even include a fly. Most of my underwear doesn’t have flys and I have gotten used to it.


Three standard types of flys in men's underwear for briefs, boxer briefs, and trunks.


  • Penis Pouch: “A trunk for your junk.” According to Hanes, 71% of all men have never tried underwear with a pouch. Nooooo! Your penis and balls need their own space – like a guest house – and you should treat them well. A single pouch means one space for both your balls and penis. These pouches could be physically separated from the rest of your groin or not separated. Underwear with physical separation costs more, but are generally more comfortable. A dual pouch means two separate spaces for your penis and balls. I detail my experiences with Seperatec’s dual pouch in this blog post.
  • Elastane/Spandex/Lycra: These three materials – which are mostly interchangable – provide stretch to your underwear and I consider a must have. For cotton and polyester/nylon blends, I recommend at least 8% elastane/Spandex/Lyca, however 10-15% is even better (20% is the highest end for reference). For softer materials like modal and bamboo, 5-8% is plenty.
  • Branded Waistband: Let’s be real, a lot of people will see your underwear waistband eventually, even if you do your best to try to hide it. Do you want your waistband to proudly show the brand you are wearing (think Calvin Klein), or do you want to be more low-key and not be a walking advertisement? The design of the waistband is really a personal preference, however I tend to prefer more conservative waistbands.