Raise Your Game: It’s Time to Update Your Soft Wear

A man's style is best judged by what he wears when no one's looking. Even if you're just reading the paper alone on a Saturday morning, it makes a difference if you have something to lounge in that's as well-made and flattering as your streetwear. It shows you always maintain high standards. So instead of boxers, try a pair of sweats that are cut slim and straight, just like a good pair of jeans.

Before anyone hits the streets in an old pair of sweats because GQ said it's cool, understand this: The out-and-about look here works because there are now pants that are more structured than ever before. (Notice how extra seams give these real shape.) That's what allows you to dress them up with something like a buttonfront shirt—instead of just wearing a tee.

1. Pile It On

Forget about "matching" colors. This looks great because it feels so accidental.

2. Join the Band

Designer details like striped bands make it clear you didn't buy this at the bookstore back in college.

3. The Suited Route

To wear a sweatshirt under a suit, make sure the sweatshirt fits snugly, so it won't add any bulk.

4. Color Up

Like its cousin the hoodie, a sweatshirt is a foolproof way to work in a bright tone.

Thom Browne New York, $300

We told you high-end designers have gotten in on the game: These are by Thom Browne, a man otherwise known for suits that cost serious coin.

Aviator Nation, $75

These faded, comfy shorts are long enough to throw on over trunks at the beach.

Club Monaco, $60

Your new gym shorts—new as in replacing those mesh saggers you've had too long. Upgrade to these.