Style-Question: Hat and Leather Jacket?

[Hal]

I think the newsboy cap style compliments a leather jacket very nicely.

There's a good photo on Aero's Facebook page of a guy in a cap and leather jacket...

The Failsworth caps Aero sells aren't as wide as most of the vintage repro options out there, but they are very nice - more of a 50s than a 30s cut, IMO. And insanely cheap by comparison.... buy both brown and grey, they look great with leathers. I wear mine all the time when I'm going more casual, with denim, or when it's too windy for a brimmed hat.

Sold on the newsboy for a super casual look.

I tend to think that, when the outer garment is of jacket length, the best accompanying headgear is a cap; to me the trilby/fedora looks better with longer coats like overcoats or trench-coats. Caps also go well with some but not all long coats.

 

[tropicalbob]

A fedora doesn't look good with a suit? A tweed jacket?

 

[Hal]

A fedora doesn't look good with a suit? A tweed jacket?

I was simply expressing an aesthetic preference (to me the shape of a crowned hat aesthetically balances a long coat and that of a flat cap balances a short jacket). I'm not dogmatically saying that the combinations you cite don't look good.
My attitude to headgear is practical rather than stylistic, so I just wear a straw hat for protection against the sun and a trilby/fedora for protection against cold with an overcoat and against rain with a trench-coat or other raincoat. Let's not give way to what might be called "hat fundamentalism" whereby the headgear is the be-all and end-all - that could have been a major contributor to the hat's 20th-century decline.