When people like me… you know, internet menswear weirdos… tell other men to dress better, usually the suggestions we give include pants or trousers with a particular feature.

That feature is the slit pocket on the side-seams. Basically, regular “dress pants” pockets. Like this…

I never really gave them much thought.

But then I became a dad and actually had to carry a bunch of junk in my pockets. That’s when I realized that they aren’t all that great.

Why?

Well, it sounds almost too simple… but stuff always falls out of them!

I can’t be the only one who has noticed this.

If I’m wearing a pair of chinos and I cross my legs while sitting (or move around in basically any way), my spare change and pocket knife come tumbling out if the pocket’s opening comes anywhere close to parallel with the ground.

This always struck me as a rather silly design flaw, especially on chinos which are military-inspired, casual pants.

Now, one could remedy this by simply carrying most things in one’s jacket pockets. I do this and it works beautifully. One of the best things about wearing a sport coat, blazer, or suit jacket is that I can carry so much stuff!

But most guys aren’t wearing tailored jackets on the regular. They’re more than likely wearing something like the “elevated casual” I wrote about a little while ago.

And if they aren’t wearing jeans, then they are probably wearing chinos or some other more formal pant with side-seam pockets.

And they’re possibly disliking this new elevated style of theirs since their stuff is falling out of their pockets! It is, in their minds, yet another example of the impracticality of classic menswear!

I get it! I’ve never liked side-seam pockets (or “slash” pockets, or whatever you want to call them).

I have always preferred 5-pockets pants.

The problem with 5-pocket pants is that they often look too casual since they are structured like jeans. But I find that that’s hardly a real problem.

I said in my “elevated casual” article that most of the “nicer” instances men find themselves in (coffee dates, parent-teacher conferences, office visits) require that particular dress code. That dress code is NOT super fancy, so things like 5-pocket pants (even jeans!) are usually ok.

Heck, even if you wanted to put on a sport coat, 5-pocket pants are still fine! Like with this outfit from a couple years ago…

Basically, 5-pocket pants are fine for 99% of what men need nice clothes for.

They go with loafers, boots, sweaters, sport coats, oxford shirts, polos, boat shoes, leather jackets, flannel shirts, and pretty much everything else just below the formality of something like a navy blazer.

That’s a lot!

Since I am the dad to two little boys, I find that my 5-pocket pants perform much better in almost all scenarios than my side-seam pocket pants. Not only can I carry the boys’ toys without worrying about losing them, but I don’t have to worry about MY stuff falling into their hands, like my aforementioned pocket knife.

Also, 5-pocket pants are excellent for when I am out and about with my kids. When I am in a crowded area like a museum, park, or subway, I usually take my wallet out of my back pocket and place it in one of my front pockets for safe-keeping. I have done this ever since I was pick-pocketed on a Bronx-bound 6 train! The front pocket of a 5-pocket pant is almost impossible to pick-pocket.

Would I wear 5-pocket pants with a tie? No. Would I wear them with a navy blazer? No. Would I wear them with a spread-collar, French-cuff shirt? No.

But I do find that I can wear them with the vast majority of my wardrobe including some of the smarter items like cashmere sweaters and tailored jackets (albeit the rougher ones).

So, even though I love my chinos (and all my “nice” pants), I really feel that the 5-pocket pant is the best choice for busy dads who want to keep their stuff secure, especially when not wearing a jacket (since you can use the jacket’s pockets instead).

Yes, 5-pocket pants are a step down in formality. And regular chinos are actually more versatile since you can wear them casually and a bit more formally (like with a tie and a blazer). But the most versatile doesn’t always mean the most useful.

A pair of khaki or olive-colored 5-pocket pants will serve you in almost all situations where you need “nicer” pants.