Shopping Roundup: 20 Pants for Fall and Winter

Shopping Roundup: 20 Pants for Fall and Winter

From casual twill to dress trousers
hm trousers

By Megan Collins | Last Updated: Oct 24 2017 | 3 min read

Look, are fall pants as fun to talk about as fall jackets? No, of course not. Or sweaters? Don’t be ridiculous. Pants remind us of how big our butts are, and how we probably didn’t need that second piece of pizza last night, and how we wish our legs were longer so we didn’t have to get every single pair of jeans we buy hemmed before we can wear them.

Or maybe that’s just me, and you l-o-o-o-o-ve wriggling into pair after pair of pants when shopping, and the variety of swapping out twill 5-pocket pants one day for dress pants the next, and chino joggers the day after that. 

At the end of the day, unless you’re Donald Duck (and if you are, hiiiiiiiiiiiiii!), you need to wear pants, like, most days. So we rounded up a few of our favorites for fall, from office formal to weekend warrior-casual.

Below, 20 fall pants for guys:

1. Carhartt WIP Sid Pant, $102

carhartt pants

2. Acne Studios Brobyn Pique Trousers, $410

Acne Brobyn pique trouser

Wear it well: These tailored and unhemmed trousers are the ultimate streetwear pant for a working man in the city. Yes, they’re expensive; they’re also really well-made, so unless you size out of them, you’ll have them basically forever.

3. Brooks Brothers Deco Trousers, $248

Brooks Brothers Regent Fit Black Watch with Deco Trousers

Wear it well: For the guy who’s not so shy

4. Counter Trousers, $240

counter trousers

5. Save Khaki, $140

save khaki slim twill trouser

Wear it well: These garment dyed twill trousers are an everyday pant that can be paired with any color shirt and a patterned jacket or sweater.

6. Wings + Horns knit wool “officers” pants, $265

wings horns pants

Wear it well: A hip and modern version of a dress trouser, these pants can be dressed up or down with a sport coat and dress shoes, or a sweater and sneakers.

7. Banana Republic, $118

banana republic windowpane dress pants

Wear it well: The windowpane adds a l’il somethin’ somethin’ to this stretch performance pant.

8. H&M, $50

hm trousers

Wear it well: Sure you could wear these with a button-up, but we like it the way H&M styled these suit pants—with sneakers and a slim-fit turtleneck.

9. Topman cropped smart pants, $70

topman cropped trousers

Wear it well: Yes, they’re cropped. Yes, you can pull them off. How do we know? We already showed you how to wear ’em here and here.

10. Guess, $49

guess sloane skinny suit pants

11. Beams Plus, $150

Beams Plus Slim-Fit Cotton-Blend Corduroy Trousers

Wear it well: Electric blue corduroy 5-pocket pants? Yessir.

12. Club Monaco, $98

club monaco pants

13. Todd Snyder olive infantry cargo pant, $245

todd snyder cargo pants

14. Van Heusen, $70

van heusen pants

15. Ministry of Supply “Going Places” pant, $94

ministry of supply pants

16. J.Crew, $128

j.crew bowery pant

Wear it well: Lookit that texture! Lookit those boots! Lookit ’em on you, and soon

17. Jack & Jones Intelligence, $79

camo cargo pants

Wear it well: Did you think we’d make it through a post on pants and not share some camo?

18. Dockers Stretch Slim pants, $50

dockers stretch khaki

19. Bonobos “Weekday Warrior” pant, $98

bonobos weekday warrior blue

20. Unis Gio Skinny black cotton twill, $2k

gio skinny black

Wear it well: True story, an old boyfriend had a pair of Unis’ Gio Skinny, and I wore them with wedges and a tank in the summer and looked real cute. What, that doesn’t help you figure out what to wear with them? Fine. Try dressing them up with an untucked OCBD and brown boots, or down with your favorite pocket tee and sneakers.



I started Style Girlfriend to help guys look, feel, and act their best.