5 Workwear Pants Outfits for Guys

5 Days, 5 Ways to wear these sturdy bottoms

By Gabi Meyers | Last Updated: Jan 27 2020

Workwear pants are a casual alternative to jeans (perfect for No Jeans January!) that look and feel more rugged than chinos.


It should come as a surprise to exactly no one that I’m very into this “shipster” style that Megan recently wrote about over on The Inventory. Think: hipster-meets-salty old fisherman vibes.

An essential part of this 2020 trend? A sturdy pair of pants. My pick for you today? Workwear pants.

What are workwear pants?

Super durable, these pants are usually made with a canvas material and a slightly wider leg. Elements like tool pockets and a hammer loop might not be utilized, but it’s nice to know they’re there.

How to wear workwear pants?

Here’s the great thing about workwear-inspired bottoms. Much like Team SG’s beloved 5-pocket pants, you can basically wear them instead of jeans in any outfit. They’re hold up well and are easy to clean — no dry clean only tags here!

To keep the wider leg on this style from feeling too relaxed, try rolling up the pant legs and showing off those ankles!

How to wear workwear pants five ways:


loafers: G.H. Bass, $110 | glasses: Warby Parker, $95

Wear it well: Dress up your workwear pants with a structured sweater and penny loafers.

If you’re feeling extra daring, wear the loafers with white crew-length socks. If you’re worried that you’ll look like an extra from Grease, don’t worry! Wearing gym socks with street clothes is very hip and cool in 2020!

Want more sweater outfit ideas? You got ’em.


sweatshirt: Saturdays NYC |bandana: United by Blue | socks: Pair of Thieves

Wear it well: Keep things casual cool in elevated sneakers and punchy accessories.


henley: Bonobos | sneakers: Vans (similar)

Wear it well: Don’t overthink it; you can wear your workwear pants like your favorite jeans or 5-pocket pants.

Think: A bomber, henley, and skate sneakers combo that would look just as cool with dark denim.


raincoat: Stutterheim | tee:Madewell | sneakers: Converse

Wear it well: A high cuffed hem keeps you from getting the dreaded soggy pant bottoms when spring showers hit.

Weather-resistant shoes will help, too. Team SG picked their favorite pairs here.


denim jacket: Levi’s | shoes: similar | bracelet: Miansai

Wear it well: A camp collar shirt, denim jacket and some lace ups can take your workwear pants out for a drink.

Shop #SGapproved workwear pants

Want to see more ways to wear your favorite pieces? We show you 5 ways to wear a leather jacket, cropped trousers, and contrast sole shoes.