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The Undisputed Best Boxer Briefs for Men (After Testing $400 Worth of Different Underwear)

I needed new underwear and a lot of it. Instead of buying all the same, I decided to go on a boxer brief buying spree. I bought many different brands. Here's my analysis of the best boxer briefs for men.

Man wearing boxer briefs

I’m a batch clothing shopper.

When I need clothes, I buy a wardrobe all at once. Several jeans, shirts, socks, shoes, etc. Then I’m good for a year or two.

It’s the same with underwear.

I don’t buy a few here and there. I buy dozens. Wear them out. Buy a few dozen again and toss the old ones.

This was my underwear buying spree year.

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Instead of buying all the same brand and type of underwear, I bought many, and I mean many, different types and brands of underwear for men.

Here are my findings for the best underwear for men.

My favorite boxer brief underwear for men for various purposes

My analysis and conclusion is based on spending over 0 on many different brands and types of men’s underwear. I then wore every type over the course of four weeks.

The most important feature for my number one pick for everyday wear is comfort. I don’t like too snug, but I don’t care for loose like boxers.

Here’s my analysis.

Related: types of men’s underwear

#1. Best boxer briefs for men for everyday wear: Calvin Klein

Calvin Klein Men's Cotton Classics Megapack Boxer Briefs, Black (7 Pack), S

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My choice for the best boxer briefs for everyday wear was a no-brainer. I knew as soon as I put this Calvin Klein underwear on that it was the best out of all the different brands/types I purchased for everyday wear.

They’re snug, but not too snug. You have room for comfort but they aren’t loose like boxers (I’m not a boxers fan).

They are very breathable, lightweight cotton (not silky or synthetic material). The elastic is snug and decent quality that doesn’t tighten too much around your waist.

I ordered large for all underwear packs including the Calvin Klein pack and this fit me the best.

They’re somewhat long but stay concealed when wearing shorts.

It’s been 4 weeks since my huge underwear buying spree and I reach for these first every time.

My only complaint is the tags are long, and yes there are more than one tag. Tagless would be nice.

The best boxer briefs for men for sports and fitness: Puma Men’s Tech Boxer Brief

Puma Men's Classic Premium Fit 3 Pack Boxer Briefs (Black, Small)

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When active, snug is good.

I have no shortage of snug underwear now.

If forced to pick my favorite underwear brand for sports and fitness, it’s the Puma Men’s Tech Boxer Brief. These are long and snug. I don’t mind that they extend beyond shorts – in fact it looks good.

These are designed for sport and compared to all the other underwear I bought and tested, these were the best for many different activities including tennis, hiking, running, jumping on a trampoline and cycling.

These are entirely synthetic materials that wicks moisture away which I love. That plus the fit make these my go-to sport and activity boxer briefs.

The best sexy boxer briefs for men: Calvin Klein Steel Micro Boxer Briefs

Calvin Klein Men's Steel Micro Boxer Briefs, black/black/black, Medium

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Including in my spree are some “sexy” underwear. I figured why not toss them in for fun.

Once again, Calvin Klein wins, but it’s a different type than the one listed above as my favorite everyday wear underwear.

For best sexy boxer briefs, it’s the Calvin Klein Steel Micro Boxer Briefs. These have a thick silver band. They’re snug and silky smooth. They’re perfect for setting the right mood.

My second favorite boxer briefs (for everyday wear)

What’s interesting is I don’t really have any underwear that stands out as my second favorite. The rest are all lumped in together.

None of them are bad but none stand out as a strong second choice.

Once I go through my Calvin’s, I don’t really care what comes out of my packed underwear drawer. They’re all pretty much the same to me except for the boxers.

However, I have do have a choice for best underwear for sports. I play tennis weekly, run sprints several times per week, go mountain biking and hiking regularly.

Underwear tested in this analysis

Below are all the different brands and individual underwear I bought, wore, tested and considered in this analysis.

Note that aside from one pack of briefs, I bought only boxer briefs since that’s my favorite style of underwear by far.

Calvin Klein Men’s Cotton Classics

Calvin Klein Men's Cotton Classics Megapack Boxer Briefs, Blue (7 Pack), M

This cotton, lightweight breathable boxer brief by Calvin Klein comes in a pack of 7, which is great because they’re my favorite. I’ll probably buy more. The assorted colors are good. I don’t much care about color. As set out above, the above are my favorite boxer briefs.

Counting Stars Mens Underwear

Counting Stars Mens Boxer Briefs Black Cotton Mens Underwear Boxer Briefs for Men Pack of 5 with Pouch Fly S

As you can see, the Counting Stars are a more snug boxer brief. They are 95% cotton and 5% spandex.

I can attest that they are snug. It’s suggested if you’re on the border of any sizing to get the larger size. I agree. When you wear these, it’s like they’re painted on. I like them fine and wear them but they aren’t my first choice.

They’re definitely decent for sport and activity.

Puma Men’s Tech Boxer Brief

PUMA Men's 3 Pack Tech Boxer Brief

The Puma Tech Boxer Brief is really designed for sport. It’s comprised of 15% Spandex and 85% Polyester. In other words, these are synthetic underwear which I like for sport only (no everyday wear).

Because it’s a synthetic material (15% Spandex and 8% Polyester) , these wick moisture away which is a huge bonus. I tend to sweat a lot so these are my go-to fitness/activity boxer briefs.

Calvin Klein Men’s Microfiber Stretch Low Rise Trunks

Calvin Klein Men's Microfiber Stretch Multipack Low Rise Trunks, Black, Medium

These are tighter than they look. I was surprised.

They are not cotton; instead 90% Polyester and 10% Elastane. They’re also shorter than most boxer briefs.

I didn’t chuck them out; I’ll wear them but they aren’t my favorite.

Hanes Tagless Exposed Waistband Boxer Briefs

Hanes Men's Tagless Exposed Waistband Boxer Briefs, Assorted, X-Large

I’ve worn Hanes underwear and t-shirts for years. Solid brand. Good value for money. These are no exception. They cost less than other boxer briefs set out in this analysis so if on a budget these will do perfectly well.

However, they aren’t quite as nicely fitted as the cotton Calvin Klein boxer briefs I prefer. These aren’t sport briefs either. Of course, they’ll work but they don’t have the comfort for activity and wicking tech that the Puma boxer briefs above have.

Calvin Klein Steel Micro Boxer Briefs

Calvin Klein Underwear Men's Steel Micro 3 Pack Boxer Briefs, Dark Midnight/Mink/Cobalt, Blue, Black, Large

If it’s sexy time you want and you don’t want to go skimpy, these are sexy boxer briefs. I feel good in them although they are snug… more snug that they appear.

I love the wide band which gives it some cache. And yes, I don’t just reserve these for romantic times; I wear them as daily wear as well.

Gildan Regular Leg Boxer Brief

Gildan Men's Regular Leg Boxer Brief Multipack, Black (5 Pack), Large

The above Gildan fitted boxer briefs have a sport appearance and are fitted for sport but are 100% cotton. If you like snug and everything held together, these are a good choice.

I’m not big on too snug so they didn’t make my first pick but they’re decent boxer briefs.

Does it really matter which boxer briefs you buy?

I admit, I’m splitting hairs above.

While I do reach for my cotton Calvin Kleins first, I don’t really care all that much.

It’s amazing how much you can end up spending on underwear when you need a whole new batch. This last spree was no exception.

FAQ

What are boxer briefs?

They’re a hybrid of boxers and briefs.  They’re longer down the leg like boxers but snug like briefs.  You enjoy the benefits of both.  They come in a variety of materials and designs for different activities.  There are everyday boxer briefs you can wear for work or hanging out and then there are boxer briefs designed more for athletics and movement.

What brand of boxer briefs are the best?

After trying Calvin Klein, Puma, Hanes, Counting Stars, and Gildan brands, my favorite by far is Calvin Klein.

What are the most comfortable men’s boxer briefs?

For me (6′ 3″, 220 lbs.) Calvin Klein’s Cotton Classics are the most comfortable. They’re the type I reach for first.  They’re snug, but not too snug.  They don’t ride low in the rear.  The waist stays in place without being restrictive.  The fabric is soft but it’s not silk.  All-in-all, these are the most comfortable for me.

Are boxer briefs comfortable?

Yes. For me they are the most comfortable type of underwear.  They will be more snug than boxers so if you don’t like the snug feel at all and prefer room, you won’t like boxer briefs; stick with boxers.  I prefer snug with more coverage than briefs offer.

Why do guys wear boxer briefs?

Boxer briefs are a great in-between underwear between boxers and briefs.  They’re my preferred style of underwear by far.  You get the coverage offered by boxers and the more snug feel of briefs.  They’re great for everyday wear and athletics.  In fact, I often head straight to a tennis or squash game wearing the boxer briefs I’ve worn all day.  All-in-all they are a versatile underwear that is great for any occasion.

Do guys wear briefs under boxers? 

I can’t speak for all men, but I suspect that few, if any men wear briefs under boxers. That would defeat the purpose.  The last thing I want to do is cram two pairs of underwear on under a pair of pants.  In fact, this is a good explanation for the popularity of boxer briefs. They’re the best of both boxers and briefs.

How should boxer briefs fit?

Having bought and worn many different styles of boxer briefs, materials and brands, here’s how they should fit.

Waist: snug so they don’t slide down but not restrictive.  I hate the feeling of waists from underwear or pants cinching into my abdomen.

Rear: Snug but sufficiently room so they don’t get pulled down in the rear.  If you bend over or set and crack is exposed, that’s not a good fit. They should remain in place no matter what you’re doing.

Legs:  Boxer briefs extend part way down the upper thigh and should be snug all the way down.  You don’t want them pinching into your leg but you don’t want them flapping around either.

Crotch:  I have one pair that’s too tight in the crotch and it’s annoying.  Again, you want it snug enough to hold equipment in place while moving around (even being active) but not so tight as to generate a squeezing feeling.

How many boxer briefs should you buy?

Haha, funny question because this goes to how often you change your underwear (hopefully daily) and how often you do your laundry.  I think a safe number is enough to see you through two to three weeks which would be 14 to 21 pairs.  I personally like a month’s worth, which I have but that’s overkill.

How can you save money on underwear?

This is easy.  Wait until your preferred brand (or any brand and style if you don’t care) has a sale, and load up with 14 to 30 pairs.  Black Friday is a great day to wait to buy staples like underwear because you know many brands will offer steep discounts so  you can load up and be set for a couple of years.  After Christmas can be a good time to buy underwear as well when many merchants and brands offer sales.  The point is whe you see a good sale, buy all you need plus some more.

Why do boxer briefs ride up?  How do I stop boxer briefs from riding up?

The main reason boxer briefs ride up is they are too small for you or the wrong cut.  I’ve bought enough brands and styles to understand that not all brands and styles are made for all guys. For instance, the Hanes boxer briefs ride low on me.  They’re too tight in the rear which makes them not ideal. The same size with Calvin Klein Cotton Classics does not have this problem.  They are roomier in the rear.  If your boxer briefs are riding up, they are the wrong cut, style and/or size.

Are boxer briefs the same as trunks?

No, they are not trunks.  Trunks is slang for a swimming suit.  Boxer briefs are a particular style of underwear.

Do boxer briefs help with chafing?

They can if the chafing is in an area where boxer briefs cover.  However, if chafing is a recurring problem, you may opt for longer underwear for more coverage.