Pair of Thieves Review: Is This The Ultimate Underwear Range?

My brother-in-law is that guy.

He manscapes, he wears jeans that cost more than our monthly mortgage payment, and he uses more hair product than any woman I’ve ever met. He also owns a ridiculous amount of underwear—in all the colors and patterns.

I am the other guy.

I buy new underwear when mine start to disintegrate. Or when I head for the bed and my wife gets that haunted “how is this my life?” look in her eyes. Often these situations occur at the same time.

Pair of Thieves Underwear

In my last fit of underwear-buying extravagance, I ended up on the Pair of Thieves website.

My brother-in-law leaned over the back of the couch to check out my browsing. “Dude,” he pointed his manicured finger at my laptop screen, “Pair of Thieves underwear are the business.” My wife flapped a pair of my hole-riddled Walmart boxer briefs aggressively by the washing basket.

And that is the story of how I became the proud owner of six pairs of Pair of Thieves underwear.

Here’s what I think—and why I ended up with that many.

Pair of Thieves Underwear Review

A quick scroll down the Pair of Thieves men’s underwear page is a little daunting. There are just so many choices.

pair of thieves underwear review

A veritable rainbow of solid colors and bold patterns and different styles to appeal to the consumerist in me. Fortunately, I’ve learned the underwear selection trick, and I’m here to guide you.

Ok, it’s not a trick. It’s just a selection process that goes like this:

  • Choose from either the Cool Breeze or Mega Soft line, then
  • Decide if you’re a boxer briefs, long boxer briefs, trunks, or briefs guy, then
  • Go nuts (come on, how could I resist?) over the colors and prints available to lovingly cup your junk as you go about your day.

I’m all about the easy life, my friend. So below, I’ve broken down both Pair of Thieves men’s underwear lines for you.

Pair of Thieves Cool Breeze

Cool Breeze Boxer Brief

In another life, an ex-girlfriend bought me a pair of underwear for Christmas. The packaging said “put them on ice!” and so I put them in the freezer before wearing them. Sure, I smelled like mixed vegetables, but the exhilaration of that chilly on my willy was a sensation I’ll treasure forever.

Cool Breeze feels a little like that (minus old freezer smell). The micro-vents allow cool air to circulate around your meat and two veg, the advanced fabric finish stays cool to the touch throughout the day, and the mesh polyamide and silicone wash wicks moisture away fast.

I’m usually a boxer briefs guy, so I went with 2 pair of the standard 5” in-seam for my first pair, and then a long boxer brief for my third, since I like a little more coverage when I’m pretending to exercise. The long boxer brief has a 7” seam, but all the same bells and whistles.

What bells and whistles? I hear you ask.

Cool Breeze Boxer Brief

Aside from the fancy mesh fabric that feels like silky refrigerated goodness against my skin, there’s also the 4-way stretch, an easy access, flat-seam fly, and low-profile flat stitching all over—which, I have learned, is code for no chafing.

Who knew? There’s also an ultra-soft waistband that doesn’t roll down or twist up when I do man-stuff (like, y’know, think about the gym membership I can’t use anymore).

The Good…

  • Generous in-seam on the long boxer brief (7”) and the standard boxer brief (5”) with no ride up.
  • Super cool fabric feel.
  • Good breathability thanks to that cooling mesh
  • Quick drying. More on that in a minute.
  • Low-profile seams to stop chafing.
  • Soft waistband doesn’t dig in and does a valiant job staying where it’s meant to be.
  • No riding up around my thighs with either style.Ultra-durable—after months of continuous use, I don’t see any pilling in the fabric or pulling at the seams.
  • Ultra-durable—after months of continuous use, I don’t see any pilling in the fabric or pulling at the seams.

I can’t bullet-point this, because it deserves its own section: awesome selection of colors and prints.

The standard Cool Breeze boxer brief comes in 15 solid colors and 19 prints, with names like Filla Vanilli Buster, Wingman, and Pork Barrel Saving. I went with Where Is Everybody? plus The Solid Gold Black (it’s black, FYI) and The Solid Tomato (a bold red with a gray waistband—my favorite pair).

The long boxer brief is slightly more limited in its offerings, with 6 solid colors and 11 prints. I have it on good authority that the Delfonics print is a winner for accentuating your package.

Interestingly, the black long boxer brief is the only pair in this range that doesn’t have the Pair of Thieves branding on the waistband—and I’m not even mad at the branding. It’s a simple imprint over the pouch, doesn’t wrap around, and doesn’t do the annoying thing where the brand name overlaps at the back and makes the seam uber-obvious.

The Bad…

  • Can too many choices be a bad thing? If not, then I’ve got nothing for you in this section. Move on.

Best for…

Everyday wear—ultra-comfortable for travelling, working, running errands, and camping in 90°+ heat. The long boxer brief is a solid choice for biking, jogging, and hiking comfortably, thanks to the extra coverage.

Pair of Thieves Mega Soft

Mega Soft Boxer Brief

I don’t think I’m overstating when I say that the Mega Soft offering from Pair of Thieves is like a comfort-blanket for my man-bits. The fabric—47% Modal, 47% cotton, 6% Spandex—is 100% snuggly soft and stretchy. It’s also breathable—although probably not to the same level as the Cool Breeze line.

This line might not offer the same delightful cooling effect of its Cool Breeze sibling, but it delivers on moisture wicking. And with this level of crazy softness, I practically live in my Mega Soft slim fits when I’m at home.

Style-wise, the Mega Soft line delivers a looser fit boxer short, boxer brief, trunk, and brief. I decided to shake things up with this range, and went with the boxer short and trunk.

The Good…

  • Generous in-seam on the boxer short (4.5”).
  • 1.5” in-seam on the trunk and a low-rider waistband make it a showy pair for date nights.
  • Barely-there feel.
  • Super-soft and comfortable.
  • Quick drying.
  • Same low-profile seams as the Cool Breeze line for zero chafe.
  • Waistband is soft but sturdy to minimize roll-down.
  • No ride-up.
  • Durable and high quality: no pilling, piling, puckering, or fuzzing so far.

The Bad…

  • Not a negative, but I think the Cool Breeze line spoiled me. I miss the color choices, although the Mega Soft offering delivers 7 solid colors and 13 prints that vary from classy to Cat Power (seriously, that’s its name).

Best for…

This is an ultra-versatile underwear line that’ll take you anywhere.

My Overall Opinion of Pair of Thieves

Pair of Thieves underwear may have overwhelmed my new-shopper mind with all their style choices, but it’s made me the man I am.

For real—I cannot be the other guy in hole-y, cardboard-like underwear again. Pair of Thieves underwear are ultra-comfortable, lightweight, breathable, and deliver on their promises—whether you’re looking for a Cool Breeze for your boys, or a Mega Soft banana hammock as you live your best life.

Not sure which line sounds better? Try both with a Mega Soft / Cool Breeze 2 Pack!

About the author

Kelsey Summers

Kelsey is the lead editor of Undywear.com. She's a fashionista who's written for Glamour, GQ and others. She enjoys breaking the stigma and taboo around underwear and writing about all things fashion.