Ask Lemmy

I got some Ergowear boxer briefs and briefs, super comfortable and plenty of space for everything to have it's own place without getting squished.

Only downside is they aren't that cheap, though maybe there are some cheap copies out there

Boxer briefs are the best of both worlds. Not too tight like a regular brief underwear, not too loose like boxer shorts, and still has adequate ball support.

They’re not cheap, but I have been rocking lululemon boxer briefs since roughly when the pandemic started. They’re cut so that you’ll have a nice pocket for the old wedding tackle, and the fit is quite flattering (or so I have been told).

You can occasionally snipe discounts on their website, or find deals at outlet locations.

I think I used to be in the same situation, used to always go for boxer-shorts since i liked having the swinging freedom, but my balls would get uncomfortable.

In comes Dual-Pouch underwear, best of both worlds for me. They look like normal underwear except they have a hole to put the penis in so it drops to the second pouch.

You get a good ball support and you don't have to squish your dick for it or the other case where everything is free, but so are the balls. This fixes that for me

I got the brand 'Separatec' style: everyday

I have been free balling it most of my life.

I did a thing a couple years ago where I dropped about $500 buying every style of boxer brief that looked appealing or had a strong fanbase. I tried saxx, Duluth, all citizens, meundies, bn3th, Mac Weldon, Lululemon, Tommy John, separatec, and probably a few others.

All Citizens are my winner overall - the BN3TH are also really nice - I actually like their cuts and design better, but the materials don't hold up nearly as well as the All Citizens. All Citizens are also much better value, IMO.

For the All Citizens, I'm specifically talking about their Paradise Pocket boxer briefs. My legs are proportionally beefy in comparison to my waist, so it's also nice that All Citizens offer an "Athletic Fit" option that keeps the legs from being overly tight. Just snug enough not to ride up without pinching or leaving a visible line visible through pants.

MeUndies thongs for men are absolutely fantastic and my go to daily underwear. They take about a day to get used to but after you do you won’t want to wear anything else.

SAXX

They are pricey but totally worth it. They last a long time, are very comfortable and have a pouch for your stuff. You can usually find deals on their website for things like discontinued holiday prints. I don't really care what mine look like so I wear a lot of Christmas themed boxer briefs. I'd recommend the Vibe.

Get a meundies account for a month and order one of each style that you're interested in. Then buy the style you like. Their model (subscription) sucks but their underwear is comfy

Got myself some StepOne boxers, best undies I've ever owned no questions asked. Miles better than anything else I've worn, I'm incapable of going back to lesser pants now. They are made with bamboo fiber, have a low friction glide panel between your legs and have a pouch for the junk to sit in. They aren't cheap but worth every penny in my opinion.

Duluth Trading men's "Buck Naked" boxer briefs are pretty good.

Boxer briefs. I have a bunch of moisture wicking clothes from 32 Degrees' Cool line that I pick up when they're on sale. They've been quite good at keeping cool and dry, as well as being comfortable.

Sizes are very different depending on where you live, so I'm not sure what size you actually are. I have underwear from Asia that's XXL, and underwear from North America that's medium.

Have you tried pocketed underwear?
It'll stop your balls from flopping around without squishing your dick because the fabric is too tight. If you follow the "Keep it slick (hairless) if you want it licked" way of thinking for your balls, it'll also prevent "batwing" by keeping them from touching your thighs.

All of the underwear I wear now are pocketed, some of them are codpiece-styled, which can be fun

Boxer briefs all the way. Most of mine are Levis and I'm happy with em.

I can recommend Duluth boxers and briefs, they have a few that tend to hold you in place. They're not cheap, but they generally last a pretty long time and are comfortable. Hanes are good as well, just found they were slightly less comfortable.

Will second pouch recommendation. It's a small but significant difference.

Nothing fancy here, but Hanes makes boxer briefs with a little pouch to give your boys a little extra support.

I'm sure other brands offer a similar style, and may be even better, but I can at least vouch for the Hanes.

Have you tried boxer briefs? It's the best of both worlds. There really aren't that many different options, just try a few more and see how you feel.

Try different brands as well, they all feel different. In addition to different brands, they each have different sub types based on what material used.