There are certain fashions that look great on gorgeous people with a team of stylists. On the rest of us they just look weird. Yes, there was a time when the fedora and trench coat looked fine. I suppose they’re fine if you want to look like a confused time traveller. Just don’t expect to recreate the Mad Men aesthetic.
MEGAN: A fedora?
BILLY: Yeah, I got a trench coat, too! Now I can look like Don Draper!
MEGAN: Hmm, try on the trench coat for me.
BILLY: How do I look?
MEGAN: Just as I suspected. All you need is a mustache to complete your pedophile look.