Best Travel Shorts Cover Post - Chris wearing his Outlier shorts in front of some graffiti in Valencia

The Short List

I hate shopping.

I especially hate shopping for clothes. 

But it’s a necessary evil when it comes to finding the best men’s shorts because shorts are pretty much all I ever wear.

I don’t spend all my days reading Reddit threads about fabric and setting Google alerts for “best men’s shorts” or anything, but I do my research, ask around, and spend more time than normal looking at other men’s upper thighs.

As it stands now, these three pairs—a fancy pair, a sporty pair, and a comfy pair—are the best men’s shorts I’ve found and the ones I wear all the time.

Long Story Short

These three are the best men’s shorts I’ve found:

I’ll explain why (plus their downsides) and what criteria I apply in this post.

What Makes a Great Short?

Chris trying on the opposite of the best mens shorts.
These shorts meet exactly ZERO of my criteria.

Here, in order from most to least important, is what I expect from a great pair of shorts, regardless of their purpose:

✓ Girlfriend-Approved

No matter how great a pair of shorts is in my mind, it’s not worth wearing if my girlfriend Kim’s going to give me dirty looks and nag me every time I wear them.

✓ Low-Maintenance

I don’t want to have to iron my shorts ever, wash them more than once a month, or wear a damp pair because they took too long to dry.

And I definitely don’t want them to fall apart when I’m traveling, so they need to be durable.

✓ Easy-to-Use

They should be a plain color that matches with anything, have a flexible waistband so they stay on, and have a drawstring to stay tight when necessary without the need of a belt.

And they must be comfortable. Once I’ve decided which shorts to wear, that’s the last I want to think of them.

✓ Have Deep Pockets

I’ve lost enough phones, wallets, and pens to have learned the importance of shorts with nice deep pockets.

If one pocket has a zipper, even better. Definitely not all zippers, though. I want quick and easy access.

✓ Not Require Deep Pockets

For those unfamiliar with the expression, “to have deep pockets” means to have a lot of money, which I don’t.

So, all else equal, I rather spend my paltry pennies on other things than fabric to cover my pasty thighs.

But, as you’ll see in my picks for the best men’s shorts, I end up sacrificing on this criterion every time in favor of pairs that excel everywhere else.

The Best Men’s Shorts
(…That I’ve Found So Far)

Graffiti of couple in Mexico - girl is sassy, guy is asking what she thinks of his shorts.

The Best Fancy Shorts

Hey there fancy pants. Fancy short pants. The best ones: the Outlier New Way.

By “fancy” I mean shorts I can wear for social situations (restaurants, bars, dinner parties) and for traveling (flights, trains, bus rides).

My Pick

Outlier New Way Shorts.

Before I got my New Way shorts, I wore either a pair of standard khaki shorts from J. Crew or a pair from Myles Apparel.

These Outlier ones are miles better.

They look as good as the J. Crew shorts, but are functionally better in every way imaginable: comfort, pockets, wrinkle-avoidance, and belt-less-ness.

They aren’t quite as comfy as my Myles shorts, but Myles shorts are glorified bathing suits. Kim wouldn’t even let me wear them to restaurants. She lets me wear my Outliers everywhere. So I do.

Even amongst the fashionable Euros in Spain, I don’t stand out in Outlier shorts.

Do They Pass the Girlfriend Test?

Kim’s take:

“J. Crew meets Lululemon! They’re functional, show just the right amount of leg, and look smart.

Also, since Chris somehow manages to spill everything on himself, this green/grey/beige color can hide stains, too. A winner in my books.”


They’re so quick-drying and stretchy that the Outlier website advertises them as swim-ready.

I have no plans to swim in them, but it’s a handy feature to have when I’m sitting on the plastic seat of an un-air-conditioned bus somewhere tropical in a pool of my own sweat.

As for durability, it’ll be a couple of years before I know for sure. I know already I’ll never iron them (what little wrinkles form when I stuff them in my bag quickly disappear when I put them on) and I’ll wash them only slightly more frequently than that (they’ve already passed the nacho cheese stain test).

The only downside so far is they’re kind of tight on my thighs, so when I stand up after sitting down for a while they have temporary wrinkles that radiate from my crotch.


I just wore my Outliers on a 35,000-step day while looking for apartments here in Valencia, Spain. I wouldn’t have dared doing that my old fancy shorts. And I had zero issues.

Well, one issue, I guess.

When I did some yoga-like stretching in the park to loosen up my tight hips, they got bunched up and I had to pull down the legs to straighten them.

As for belt-less-ness, the fit and flexibility of the fabric holds the shorts up just fine ob their own. They have a drawstring, but I only use it when I carry heavy stuff in my pockets.

Deep Pockets?

The very first day I wore my New Way shorts, I stressed out because I couldn’t find my wallet. I looked everywhere for it… only to realize they were in my pocket.

It’s a skinny wallet, but still.

The point is the pockets of these shorts are the right size and place to store stuff very comfortably.

None of the pockets have zippers, though.

Not Require Deep Pockets?

A big red F for these shorts.

They cost $125.

But hey, if these shorts are as durable as they feel and as people say they are, it’s worth the investment.

The Best Sporty Shorts

Lululemon’s Pace Breaker shorts live up to their name by leading the way as the best sports shorts I’ve worn.

My Pick

Lululemon Pace Breaker Shorts.

I’ve been wearing some version of Lululemon’s Pace Breaker shorts ever since they came into existence about fifteen years ago.

During that decade and a half, I’ve introduced many challengers to the title including the best I could find from Nike, Patagonia, New Balance, Under Armour, and RYU.

None have close to dethroning Lululemon.

Do They Pass the Girlfriend Test?

Kim’s take:

“Chris wears these shorts more often than he wears a shirt in the summer.

For how often he wears them, they hold up great. Sure, the color fades every now and then but I think other shorts would do the same. And Chris can wear them multiple wears and they don’t ever stink too bad. They also dry super quick.

I’d like to see him in a shorter version (which Lululemon has) but for now, no complaints.”

Chris posing in his Lululemon Pace Breaker shorts on the seaweed filled beach in Tulum
In my defense, Kim took this photo of me in my Pace Breaker shorts for our anti-Instagram-centric Tulum travel guide.


I have to wash my Pace Breakers quite regularly, but that’s because I do a lot of sports in them. They’re not merino wool like my comfy shorts, so if I don’t wash them they, like any other sport short, smell like ass. Sweaty ass.

The good thing is, unlike other shorts I have, the fabric they’re made of doesn’t don’t get super staticky if I put them in the dryer (which I try to avoid since they hang dry fast enough).

As for durability, one pair lasted ten years but that was an exception. Usually they last me about three years before the color gets really faded and the fabric starts to wear.


Function is obviously what matters most for a sports short and that’s the reason I swear by the Pace Breakers.

In so many other sports shorts, the elastic waist band rides up or slides down or the drawstring comes loose too often. Cheaper pairs also annoyingly stick to your leg when they and you get really sweaty. My Pace Breakers have none of those problems.

They’re not perfect, though.

I use them for beach volleyball and recreational swimming and hot-tubbing and wish the pockets were of a flow-through fabric like my Outliers’ so they didn’t get sand or air pockets trapped in them.

Deep Pockets?

Most sports shorts don’t have regular front pockets, which is a pain in the ass when I want to wear them for errands and put my wallet, keys, or whatever into them.

No pain in the ass with these, because they have nice and deep front pockets. They also have a side zipper pocket which is handy for my cards, cash, and keys during workouts.

The only hole in my Pace Breaker’s pocket game is none of them are ideal for holding my cell phone while running, so I use one of these SPIbelts.

The newest model has a phone pocket on the thigh. I look forward to giving them a go whenever my current pairs give up on me.

Not Require Deep Pockets?

Their $68 price tag ain’t cheap but, like I said, they last a long time.

And Lululemon stands by their product quality. The couple of times I’ve had issues, the guys at the store replaced the shorts with new ones without batting an eye.

The Best Comfy Shorts

The only thing wrong with my super comfy Icebreaker Momentum shorts is their name, since I only use them for lazing about at home.

My Pick

Icebreaker Momentum Shorts.

If I were single I’d wear these shorts exclusively (except for sports).

I pretty much do anyway. As soon as I get home, I go to my room and change into them.

And when Kim’s not looking I wear them out in public.

They’re like a much-loved house pet: I don’t normally take them traveling because I keep my packing list light, but I miss them greatly when I’m away and rush to greet them as soon as I get home.

Do They Pass the Girlfriend Test?

Kim’s take:

“I like these more than Chris’ Roots sweatpants, but they’re still sweat-shorts.

I know they’re comfortable and I have no problem with him wearing them at home. But that being said, they’re very thin and show everything around the crotch region so I definitely don’t approve when he tries to wear them outside.”

Chris wears his comfortable Icebreaker Momentum shorts while lounging and doing work on the couch.
My Momentum shorts in “action.”


If I told you how rarely I wash my Momentum shorts, Kim would get mad at me.

That’s because they’re made with my favorite material in the world: stink-proof, super-insulating, surprisingly-soft merino wool.

And while merino wool has a reputation for not being very durable, I’ve had this pair of shorts for a year-and-a-half of heavy use and they’re still good as new.

The only downside is when I do wash them, they take longer to dry than purely synthetic shorts. I hate having to wear other shorts while I wait.


I’ve already said enough about how comfortable they are.

They feel like stretchy sweat shorts, but better because the merino fabric insulates better than cotton.

Deep Pockets?

They’re deep and tight to the body so stuff doesn’t fall out of them when I sit, lie down, and stand up.

They don’t have a zipper pocket, but that’s fine. I’m only supposed to wear them at home anyway. And the right pocket has a little coin pouch at the bottom of it, which is a nice touch.

Not Require Deep Pockets?

As with all merino products, they’re not cheap.

They’re $90. I could have bought ten pairs of regular cotton sweat shorts at Winners with that money. But I don’t care.

What’s Under the Shorts?

Beneath every great pair of shorts must be a great pair of underwear like these from Icebreaker.

When I wear my Lululemon sports shorts, nothing because they have a built-in liner.

But I do wear underwear below my Outlier fancy shorts and my Icebreaker comfy ones.

It’ll take a whole other blog post for another time to explain how I decided on the best underwear. If you insist on knowing now, my favorites are the Icebreaker Everyday Boxers.

More Cool Stuff

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