Corduroys

Slim-fit pants don't fit you right? Polo by Ralph Lauren's Bootcut Corduroy Jeans ($90; polo.com) have a generous—but not loose—cut that will easily fit over your Sorels. What Converse's canvas Chuck Taylor All Star Hi-Tops ($45; converse.com) lack in ankle support, they easily make up in style.

With a regular fit and low-key styling, Quiksilver's Sequel Cords ($50; quiksilver.com) go with just about everything, even the neon-green laces on Onitsuka Tiger's Ultimate 81's ($80; onitsuka-tiger.com), which first debuted in 1981 as a running shoe and are now part of ASICS's line of re­released original athletic kicks.

Hand-sanded along the thighs, knee, and seat, J.Crew's straight-fit, five-pocket Vintage Cords ($70; jcrew.com) look as worn-in right off the rack as most vintage duds. Quiksilver's boat-shoe-inspired Continental canvas slip-ons ($60) won't fall off; they've got just the right amount of elasticized material around the forefoot.

Nautica's 5-Pocket Corduroys ($70; nautica.com) are styled like your favorite pair of jeans, with a relaxed but not-too-baggy fit. That's Patagonia's organic-cotton-and-polyester Buckshot Flannel shirt ($75; patagonia.com) up top, and Converse's Chuck Taylor All Star Hi-Tops down low.

Khakis

Dockers' all-cotton, slim-fitting City Chinos ($52; dockers.com) look just as good dressed up as they do paired with a pair of suede Vans Chukka Boots ($60; vans.com) and Patagonia's 100 percent organic-cotton Live Simply Bear T-shirt ($30).

You can't go wrong with Gap's cotton Original Khakis ($45; gap.com). Their classic, straight-leg fit never goes out of style. Seen here with canvas Vans Classic Slip-Ons ($40) and Patagonia's organic-cotton-and-polyester Buckshot long-sleeve shirt ($75).

Room for only one pair of pants in your carry-on? Dockers' cotton-and-nylon Eco Tahoe Convertibles ($72) are dressier than your average hiking pants, and they conveniently double as shorts. In the market for retro sneaks? Consider the originals, Converse's canvas Chuck Taylor All Star Lo-Tops ($45).

With their jeans-style pocketing and chino-like cut, Patagonia's nylon-canvas Roving Pants ($75) have an office-friendly look, but with a gusseted crotch, articulated knees, and a water-resistant coating, they're designed for climbing and hiking. The canvas-and-leather Sk8-Hi shoes ($50) by Vans give a nod to the days of Dogtown.