The idea of investing in a piece tells me you'd like to have this piece for a while, and you should—it's a classic, masculine piece that will always be in style. Thus buying a modern, single-breasted option would be counterproductive to the overcoat's storied history. I'd suggest the British label's updated "Trench 19 Slim," a shorter jacket with higher arm holes for a more narrow fit while retaining the coat's classic proportions. After all, if you're buying Burberry, the trench will likely outlive you. And don't worry about being a fair-weather wearer. A non-slicker raincoat is the perfect cover when the air gets chilly.

Slim-cut trench, $950,
at Burberry.

I'd like to invest in a Burberry trench this fall, but I'm torn between a traditional or more modern style. And my bigger question is, if I wear it when it's not raining, does it make me look like a flasher?
- Michael, Boston

FYI: In 1880, Thomas Burberry invented gabardine and in 1914 was commissioned by the British military to create the trench coat.