1. Redwing Iron Ranger, basically the boots I grew up seeing my grandfather wear. He worked in the iron ore mines of northern (upper penninsula) Michigan. Seriously burly.
2. Pringle makes some of the best knitwear ever. This coat is serious style I wish I had the guts to pull off! They make great shirts as well!
3. Fall in New England can quickly turn to winter as soon as the sun sets... These are what we call Chopper Mittens in Northern Michigan, most every hunting/sporting goods store has some variety. These are a bit "fancy" but still traditional. For real authenticity... have yer gran, mom or best gal knit ya some nice wool liners, light wool for fall, heavy for winter. Your hands will be warm and happy shovelin' snow or choppin' wood or drivin' a cold car to the grocery store. These things are built to last.
4. Arc'teryx, atechnical sweatshirt. Wear it under yer jean jacket, flannel, on its own, whatever. Looks good and Arc'teryx might be the most legit outdoors technical gear ever.
5. Vans Rowley SPV. Finally a classic look on a technical modern shoe from style master Geoff Rowley.