Not every dog jacket is built the same way.
Boston’s weather swings fast — 55 and sunny in the morning, raw and windy by evening. A jacket that actually works has to handle that swing, not just look good in a photo.

Start with coat type, not breed
A short-haired dog loses heat fast and needs real insulation. A thick double-coated breed usually needs less — sometimes just wind and rain protection, not warmth. Fit the jacket to the coat your dog actually has.
Fit matters more than style
A jacket that rides up, slips sideways, or binds at the shoulders will get shrugged off within a block. Measure chest girth and neck before you buy, and check for adjustable straps rather than a single fixed size.
Waterproof and warm are two different jobs
A jacket can be warm without being waterproof, and waterproof without being warm. For New England fall, look for a shell layer that sheds rain plus a lining that holds heat — not one fabric trying to do both.
Leash access should not be an afterthought
A good jacket has a back opening or D-ring cutout so you’re not fighting the harness every time you clip in for a walk.
Let your dog break it in indoors first
Put a new jacket on for a few short indoor stretches before the first real walk. It gives your dog a chance to get used to the feel before it’s also dealing with wind, leash, and new smells all at once.