Review recently updated with comments on the new Hammock Pouch design

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Best Boxer Briefs for Men

As of December 2020


This is one of the few products on this site which rarely goes on sale and isn’t available locally. If you’re a first time buyer, make sure you take advantage of the initial sign up offer of up to 20% off. At any time, you can buy packs in bulk (3-5 pairs) for 10% off.


If you’re a repeat buyer, be prepared to pay full freight. If you can wait, Tommy John typically offers very strong promotions during major holidays like Black Friday.


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what we like

  • Fits best for those looking for: An everyday boxer brief which can be worn to work or to workouts and do not ride up
  • The second skin material is second to none.
  • It maintains the brand new silky feel even years later
  • The boxer briefs (these are the 8″ ones that cover the majority of your thigh) do not ride up at all
  • Easy to wash and dry
  • Solid color choices
  • Horizontal flys on every pair (these are admittedly super annoying at first but overtime you realize how much easier one handed access is going forward)
  • Newly added hammock pouch option is great for support, confidence and avoiding chafing

keep in mind

  • Not cheap
  • Overtime, the material can tear (1-2 years)
  • The shorter, trunks version (4.5″) does tend to ride up the leg
  • Hammock Pouch design has a completely unnecessary “Hammock Pouch” written huge in block lettering on the bottom of the pant leg


If you’re still in that stage of wearing the same $5 boxers you’ve been buying from Marshall’s or Banana Republic your whole life, it’s hard to wrap your brain around the thought of spending 5-7x that for a single pair. They’re all just basic cotton underwear and (on most days) no one else sees them but you…so why waste the money?


That’s where I was until being convinced to try a variety of higher end pairs of boxer briefs years ago and finally settling on Tommy John’s Second Skin line. Within a week I threw out all my old boxer briefs and never looked back. The silky feel of the fabric and corresponding support just provide a level of all-day comfort you don’t get from basic cotton. The legs never ride up (for the 8″ Boxer Briefs version) and the elastic band provides no irritation.


After trying several of the other major competitors in this space (including Stance, Saxx, Mack Weldon and MeUndies), Tommy John boxer briefs provided my favorite level of overall fit and lasting performance. The fabric can be subject to tears if you’re not careful with them and the shorter versions (trunks) can still ride up your leg during the course of a day. In 2020, Tommy John added a mid-length (6″ inseam) option and a Saxx-like Hammock Pouch design. While we still prefer the full 8″ versions, we are huge fans of the Hammock Pouch and think it’s worth the extra few dollar given the added support and alleviation of any possible chafing. 


Overall, Tommy John remains the best boxer brief we have ever worn. It’s one of the few articles of clothing you wear everyday and it’s definitely worth the additional investment.

Sizing Tips & FAQs

Is the Hammock Pouch worth it?

Yes, we think it is. Not only does it provide a little more support/confidence, but it also helps to alleviate any chafing. If you are prone to chafing, definitely pay up for the Hammock Pouch.


How do I decide between the boxer briefs, mid-length, trunks, relaxed fit boxer, square cut and briefs?

Unless you’re Cristiano Ronaldo, you probably shouldn’t be rocking briefs or square cut. Our personal favorites are the Boxer Briefs (8” inseam). The boxer briefs are ideal for wearing underneath shorts. Most of the ladies we polled (basically just Jill, Jackie and Julie) said they like it when their men wear trunks (4.5″ inseam), but these can ride-up during the course of a day which leads to you having to adjust them periodically. The new mid-length 6″ option is the perfect compromise between the briefs and trunks if you are undecided.


The relaxed fit boxers are too loose for our taste. But if you are a current boxer (not boxer briefs) wearer, these might be a good gateway option.


What’s the difference between second skin, cool cotton, air, 360 sport and go anywhere?

 Each one has a slightly different feel and function. They’re all useful in their own ways but our clear favorite is the second skin. If in doubt, we highly recommend just keeping it simple and going with the second skin. I own a few pairs of the Second Skin x Air line which are a lighter overall feel. The Second Skin’s are extremely light anyways, but if you’re the type that has historically gone commando often and absolutely hate the feel of any fabric down there…maybe check out the Air line for your purposes.


Can you work out in the second skin fabric?

 I personally do and I enjoy it. If you do want to work out in the second skin boxers, we recommend going with the boxer briefs (8” inseam) so they don’t ride up at all. The 360 sport is TJ’s actual activewear line which gives you the most compression. I own a few pairs of those and we have found them to be the best option for high performance compression active underwear.


Why is the fly horizontal? That just seems like a lot of extra work for no reason.

The Quick Draw horizontal fly that Tommy John uses in every pair they make is very awkward to get used to. But there are a few reasons why it’s advantageous over the traditional double flap vertical ones:

  1. Easy access – it becomes much easier to use one hand going forward
  2. It’s more breathable – instead of having two panels of fabric like there are on traditional vertical flys, heat can escape out of the top of the single paneled horizontal fly
  3. You don’t have to worry about your junk sticking out accidentally – If you don’t properly re-tuck after using a vertical fly, you can be subject to the occasional peek-a-boo which can be uncomfortable, at best, and embarrassing, at worst


How do you wash/dry them?

Machine wash cold and dry them as you would anything else in the dryer. They recommend “tumble dry low” but I sometimes throw them in on high with the rest of my gym wear without much of an issue. Just be careful not to put them in the dryer with anything sharp, like zippers, which can snag at the soft fabric.

Have another question?

Related Products & Links


A second choice behind Tommy John. Stance does make 6″ boxer briefs with the traditional vertical fly opening. If you’d like to stick to the fit and look you are used to while getting an upgrade in quality, Stance offers the easiest transition.


Lululemon – Always in Motion Boxer

Super comfortable and well fitting like most of Lulu clothes. However, I find they ride up more than Tommy Johns and there is no fly. Non-starter for us.



Tommy John took the lead from Saxx when they came out with the Hammock Pouch. This design was previously a staple of Saxx with their ballpark pouch and one of the things we loved the most about their boxers. I really wanted to love these because their ballpark pouch design is great for confidence. Like the Hammock Pouch, it’s basically the equivalent of a push up bra for men. But the lack of a fly and periodic readjusting needed to keep the legs down makes this a clear second choice:



They do a decent job putting out a very comfortable low cost alternative if you’re price sensitive. If you’d prefer to stay in the sub $10 range for underwear, these are by far your best bet. However, riding up is an issue and the structure/quality just can’t compare to Tommy John.


Mack Weldon

These guys have arguably the biggest ad spend of any player on the market. The quality is decent but we found the fit to be subpar. They’re too loose in the crotch and butt area.


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