Billy Reid, $625
Despite its old school associations with gentleman hunters and academia, the sturdy tweed jacket is getting a stylish shot in the arm this fall. The results are better-fitting blazers that retain the rustic, autumnal charm but are a tad lighter and decidedly less stuffy. Woven from cotton and lightweight wools, in both herringbone and Donegal tweed patterns, the jackets have a slightly more relaxed feel and make easy work out of layering various pieces under them as the weather cools down. Complement the texture of the tweed with a washed oxford cloth shirt and a knit tie in a darker color for an update on a timeless look that works for any occasion.