Rule No. 1:
You can go outside in sweatpants, as long as they're not the same ones you'd sleep in. Designers are doling out slimmer, tailored versions that aren't meant for the gym.

Rule No. 2:
Keep the office dress shirts in your closet, but don't underestimate the power of a good button-down—you'll get endless use out of an oxford in linen or a lighter cotton weave come spring.

Rule No. 3:
A three-quarter trench coat like this one instantly dresses up everything, from jeans to sweatpants. Think of it as your ultimate cheat when stepping out the door.

On model: Trench coat ($1,650) by Gucci, Shirt ($280) by Officine Generale, Sweatpants ($250) by T by Alexander Wang, Shoes ($140) by Clarks.

Rule No. 4:
Comfort can no longer be used as an excuse for ignoring your personal style when you're out of the office. From Margaret Howell to Alexander Wang, designers are focusing on weekend-ready clothing now more than ever.

Rule No. 5:
Clean, minimalist sneakers like the ones below are basically the dress shoes of the weekend. They work not only with a suit (which can and should be thrown into the rotation on a Saturday; see Rule 6) but with everything else on these pages as well. Buy a pair (or all four) and never think twice about what to wear them with again.

Sneakers, clockwise from top left: Giorgio Armani ($525), Common Projects ($594), Nike ($150), Comme des Garçons Shirt x Erik Schedin ($365).

Rules 6–8 →