Regardless of season, a shirtdress is always appropriate. It's easy to throw on, but always looks polished and classic. For fall, it works really well because you can layer overtop of the shirtdress in so many different ways.
I paired this denim shirtdress with riding boots for a 'right now' look. But as it gets cooler, tights can be added or a throw on a turtleneck underneath or sweater over top. Not to mention, the cinch at the waist gives it some shape making it a little dressier and therefore, work appropriate.
If you don't have a Barbour jacket, I definitely recommend one. It's a well-made classic that never goes out of style. It's casual but versatile. I have the classic beaufort (seen here) and the one seen above is from the Barbour x Land Rover collection. I got this jacket half off at the Barbour store in Georgetown. Can't beat that!!
The tote you've seen here, but I have been using it constantly. It's so well made and the blue stripes go with most of my wardrobe. It's the perfect size for commuting to work! I really love all of the MDS collection by Mark Sikes. If you are unfamiliar with Mark Sikes, his interior design work is incredible-- I love everything he does and his taste matches mine to a T!