Wearing a suit to the office isn't really an option for a growing number of guys these days. I call these guys "the new professionals," and they're typically found in creative environments like start-ups, boutique ad agencies, and design shops. A few months ago, I wrote a blog post outlining sartorial suggestions for these types, and here's a look that would work especially well for fall.
Jacket: 60/40 Mountain Parka by Apolis + Sierra Designs
Sierra Designs makes the best parkas around, and this limited-edition collaboration with Apolis makes the classic even better.
Pants: Gio Pant by Unis
The Gio pant should be considered a staple. Made in the USA from Italian cotton, they might cost you a little more, but they'll last forever—and fit perfectly.
Shirt: Flap Pocket Collegiate Shirt by Steven Alan
No matter how casual the environment, every guy should have at least five collared shirts in rotation, and Steven Alan shirts have a reputation for comfy-ness.
Boots: 1000 Mile Boot by Wolverine
Not only are they incredibly well made, but they are also versatile—you can wear them with denim, cords, or even suits (should the occasion call for one).
Sweater: Moss Shawl Cardigan by Barbour
First and foremost, sweaters should be warm and comfortable. This one fits the bill and can be tossed on over just about anything.
Bag: Day Pack by Epperson Mountaineering
For guys toting cameras, computers, iPads, and Kindles—and all at once—backpacks are functional as hell, and these days they look good, too.
Hat: Tweed Metal Plate 5 Pannel Hat by Supreme
No matter what, you should wear something that makes you feel like yourself, and a hat is a good place to start (if that's your thing). This Supreme cap combines street and traditional menswear styling to really pop.