5 Days 5 Ways

How to Wear Cargo Pants in 2020

Not your older brother's cargo pants

By Gabi Meyers | Last Updated: Feb 2 2020

This might be a controversial opinion, but hopefully coming from me, it won’t surprise you too much:

I’m totally pro-guys wearing cargo pants.

Now, you guys may have put that together when I shared 5 ways to wear the modern cargo shorts, and while there was some pushback, nevertheless, I persist.

Because, guys, you would rock ’em so well! Of course, just like with the cargo shorts, these cargo pants are not the cargo pants your mean older brother was wearing in the early 2000’s.

Today’s cargo pants fit slim through the leg. Meaning, you shouldn’t be able to comfortably hold a can of Bud Light in one pocket and..well, another Bud Light in the other.

Cargo pants are a great casual alternative to jeans, chinos, and 5-pocket twill pants. Of course, you could wear the outfits below with any of the above, too, so take this outfit inspiration however you want.

Personally, I really like the nod cargo pants give to the military trend that has been in style for what feels like forever. It makes them just interesting enough without looking “out there.”

Oh, and also, they are the perfect weight for spring weather!

The modern cargo pants are slimmer in cut, with pockets that add visual interest, without the bulk.

Below, five ideas on how to wear cargo pants in a totally modern way:


shirt: J.Crew, $60 | boots (similar): To Boot New York, $238 | watch: Shinola, $925

Wear it well: Dress up your cargo pants for a creative work place with a blazer – roll up the cargo pants AND push your sleeves up to give it a lived in look.


tee: Everlane, $20 |key tag: Various Projects, $20

Wear it well: A few pops of color make your running errands outfit, complete with denim jacket and bright sneakers, feel more fun.


boots: Oak Street Bootmakers, $462 | fragrance: D.S. Durga, $175

Wear it well: You can wear your cargo pants all the way back to cool weather, by dressing them up with a textured sweater and topcoat. You’re sure to nail that ‘rugged gentleman’ vibe.


shirt (similar): Faherty, $138| shoes: Gypsy, $166 | watch: Nixon, $80 (on clearance!)

Wear it well: A zippy, fun short-sleeve shirt, with a half zip sweater and derbies take your cargos from work to drinks.


Breton stripe shirt: Saint James, $99 | Sneakers: Converse, $95

Wear it well: A breton shirt and a suede collared jacket elevate cargos while still keeping things casual.

Shop #SGapproved cargo pants picks

J.Crew, $80


Want to see more ways to wear your favorite pieces? See five ways to wear lace up boots, a breton shirt and brown derby shoes.